CN101250091B - Synthesis of polysubstitution 2-fluorin allyl alcohol compounds - Google Patents
Synthesis of polysubstitution 2-fluorin allyl alcohol compounds Download PDFInfo
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- CN101250091B CN101250091B CN2008100590840A CN200810059084A CN101250091B CN 101250091 B CN101250091 B CN 101250091B CN 2008100590840 A CN2008100590840 A CN 2008100590840A CN 200810059084 A CN200810059084 A CN 200810059084A CN 101250091 B CN101250091 B CN 101250091B
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- 150000004808 allyl alcohols Chemical class 0.000 title abstract description 4
- 238000003786 synthesis reaction Methods 0.000 title description 3
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 22
- -1 allyl alcohol compound Chemical class 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 150000001361 allenes Chemical class 0.000 claims abstract description 9
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- XEIHLEMBJXRLEI-UHFFFAOYSA-N 2-fluoroprop-2-en-1-ol Chemical class OCC(F)=C XEIHLEMBJXRLEI-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 238000003818 flash chromatography Methods 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 2
- 229940126214 compound 3 Drugs 0.000 claims description 2
- 239000012039 electrophile Substances 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 13
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N hydroxymethylethylene Natural products OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000003682 fluorination reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000012363 selectfluor Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- OPKQXJQFEPNJTP-UHFFFAOYSA-N 1-phenylpropa-1,2-dienylbenzene Chemical compound C=1C=CC=CC=1C(=C=C)C1=CC=CC=C1 OPKQXJQFEPNJTP-UHFFFAOYSA-N 0.000 description 1
- DYHZACXDGYGUBZ-UHFFFAOYSA-N CCCCC(=C=C)C1=CC=C(C)C=C1 Chemical compound CCCCC(=C=C)C1=CC=C(C)C=C1 DYHZACXDGYGUBZ-UHFFFAOYSA-N 0.000 description 1
- MCWBAEYMPNWDNS-UHFFFAOYSA-N CCCCC(=C=C)C1=CC=CC=C1C Chemical compound CCCCC(=C=C)C1=CC=CC=C1C MCWBAEYMPNWDNS-UHFFFAOYSA-N 0.000 description 1
- KCHYGHWBOOGWAZ-UHFFFAOYSA-N CCCCCCC(=C=C)C1=CC=CC=C1 Chemical compound CCCCCCC(=C=C)C1=CC=CC=C1 KCHYGHWBOOGWAZ-UHFFFAOYSA-N 0.000 description 1
- OGXMDFMCXMZVRV-UHFFFAOYSA-N CCCCCCC(=C=C)C1=CC=CC=C1C Chemical compound CCCCCCC(=C=C)C1=CC=CC=C1C OGXMDFMCXMZVRV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- HQZFSHGTEUJEJJ-UHFFFAOYSA-N hepta-1,2-dien-3-ylbenzene Chemical compound CCCCC(=C=C)C1=CC=CC=C1 HQZFSHGTEUJEJJ-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- CXWIPHRBYYENRX-UHFFFAOYSA-N penta-1,2-dien-3-ylbenzene Chemical compound CCC(=C=C)C1=CC=CC=C1 CXWIPHRBYYENRX-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WEHMXWJFCCNXHJ-UHFFFAOYSA-N propa-1,2-dienylbenzene Chemical compound C=C=CC1=CC=CC=C1 WEHMXWJFCCNXHJ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
Abstract
Description
技术领域technical field
本发明涉及一种合成多取代2-氟烯丙醇类化合物的方法，即通过联烯的羟氟化反应高区域和立体选择性地合成α-官能团化多取代烯丙醇方法。The present invention relates to a method for synthesizing multi-substituted 2-fluoro allyl alcohols, that is, a method for synthesizing α-functional multi-substituted allyl alcohols with high regio- and stereoselectivity through the hydroxyfluorination reaction of allenes.
背景技术Background technique
多取代烯丙醇是有机合成中最重要的中间体之一，也是天然产物中最常见的结构单元之一，具有多种重要的生理活性，在生物技术领域，医药及农药等方面有巨大的开发利用价值。而氟化物由于其独特的生理活性，在医药和农药等领域得到了广泛的应用，而通过一步反应生成取代2-氟烯丙醇类化合物的方法还没有文献报道。因此能一步引入多个取代基合成2-氟烯丙醇比以往反应有很大突破。Multi-substituted allyl alcohol is one of the most important intermediates in organic synthesis and one of the most common structural units in natural products. It has a variety of important physiological activities and has huge potential in the field of biotechnology, medicine and pesticides. development and utilization value. Due to its unique physiological activity, fluoride has been widely used in the fields of medicine and pesticides, but the method of generating substituted 2-fluoroallyl alcohols through a one-step reaction has not been reported in the literature. Therefore, the ability to introduce multiple substituents in one step to synthesize 2-fluoroallyl alcohol is a great breakthrough compared with previous reactions.
发明内容Contents of the invention
本发明的目的就是提供一种有效的合成多取代2-氟烯丙醇类化合物方法。The purpose of the present invention is to provide an effective method for synthesizing multi-substituted 2-fluoroallyl alcohols.
本发明基于联烯与含氟亲电试剂的高区域和立体选择性的羟氟化反应，合成2-氟烯丙醇类化合物，反应式如下：The present invention is based on the high regio- and stereoselective hydroxyfluorination of allenes and fluorine-containing electrophiles to synthesize 2-fluoroallyl alcohol compounds. The reaction formula is as follows:
产率：37-88％Yield: 37-88%
R可以是H或者不同碳链长短的烷基，其中烷基为CnH2n+1，其中n＝2-6，Ar可以是苯基或者是邻位、间位、对位被不同取代基取代的芳基，其步骤是：R can be H or an alkyl group with different carbon chain lengths, where the alkyl group is C n H 2n+1 , where n=2-6, Ar can be phenyl or different substituents in the ortho, meta, or para positions Substituted aryl, the steps are:
(1)在室温下将联烯1加入到乙腈和水混合溶剂中，搅拌下加入1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)2，室温下反应2-20小时，加水。(1) Add allene 1 to the mixed solvent of acetonitrile and water at room temperature, and add 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octanetetrafluoroboron under stirring acid salt (Selectfluor) 2, react at room temperature for 2-20 hours, and add water.
(2)用乙醚萃取，无水硫酸钠干燥，过滤，浓缩，快速柱层析，获得2-氟烯丙醇类化合物3。(2) Extracted with ether, dried over anhydrous sodium sulfate, filtered, concentrated, and subjected to flash column chromatography to obtain 2-fluoroallyl alcohol compound 3.
本发明所述的混合溶剂中乙腈与水的体积比为10∶1。The volume ratio of acetonitrile and water in the mixed solvent of the present invention is 10:1.
本发明所述的反应原料1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)与联烯的摩尔比为1.2～1.5∶1。The molar ratio of the reaction raw material 1-chloromethyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane tetrafluoroborate (Selectfluor) to allene in the present invention is 1.2～1.5 : 1.
本发明所述1毫摩尔的α-联烯需加溶剂乙腈的量为10毫升。The amount of acetonitrile that needs to be added as a solvent for 1 mmol of α-alkene in the present invention is 10 milliliters.
本方法操作简单，原料和试剂易得，反应具有高度的区域和立体选择性，能同时引入多个取代基，产物易分离纯化，适用于合成各种取代的2-氟烯丙醇The method is simple to operate, the raw materials and reagents are easy to obtain, the reaction has a high degree of regio and stereoselectivity, multiple substituents can be introduced at the same time, the product is easy to separate and purify, and is suitable for the synthesis of various substituted 2-fluoroallyl alcohols
本发明在于发展了一种方便实用合成多取代2-氟烯丙醇类化合物的方法。The present invention is to develop a convenient and practical method for synthesizing multi-substituted 2-fluoroallyl alcohol compounds.
本发明方法所得的相应的2-氟烯丙醇类化合物产率为37-88％。The yield of the corresponding 2-fluoroallyl alcohol compound obtained by the method of the present invention is 37-88%.
具体实施方式Detailed ways
以下实施例有助于理解本发明，但不限于本发明的内容。The following examples are helpful for understanding the present invention, but not limiting the content of the present invention.
实施例1Example 1
反应管中加入3-苯基-1，2-庚二烯(86.0mg，0.5mmol)，5.0mL乙腈(MeCN)与0.5mL H2O溶解，搅拌下加入212.4mg(0.60mmol)1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)，室温下搅拌2h反应完全(TLC点板跟踪)，加入10mL水淬灭，乙醚萃取三次(30+25×2mL)，饱和氯化钠溶液洗涤，无水硫酸钠干燥，浓缩溶液，快速柱层析，石油醚/乙酸乙酯＝20∶1，得产物64.8mg 3-苯基-2-氟-1-庚烯-3-醇，产率62％，产物为无色液体。Add 3-phenyl-1,2-heptadiene (86.0 mg, 0.5 mmol) to the reaction tube, dissolve 5.0 mL of acetonitrile (MeCN) and 0.5 mL of H 2 O, add 212.4 mg (0.60 mmol) of 1-chloro Methyl-4-fluoro-1,4-diazabicyclo[2.2.2]octanetetrafluoroborate (Selectfluor), stirred at room temperature for 2h, the reaction was complete (TLC plate tracking), quenched by adding 10mL of water, Extracted three times with ether (30+25×2mL), washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, concentrated the solution, flash column chromatography, petroleum ether/ethyl acetate=20:1, and obtained 64.8 mg of 3-benzene Ethyl-2-fluoro-1-hepten-3-ol, the yield is 62%, and the product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.50(d，J＝7.5Hz，2H)，7.39-7.23(m，3H)，4.81(dd，J＝7.8 &2.4Hz，1H)，4.70(dd，J＝24.0 & 3.0Hz，1H)，2.30(s，1H)，2.07-1.87(m，2H)，1.44-1.17(m，4H)，0.88(t，J＝6.9Hz，3H)； 1 H NMR (300MHz, CDCl 3 ) δ7.50(d, J=7.5Hz, 2H), 7.39-7.23(m, 3H), 4.81(dd, J=7.8 & 2.4Hz, 1H), 4.70(dd, J=24.0 & 3.0Hz, 1H), 2.30(s, 1H), 2.07-1.87(m, 2H), 1.44-1.17(m, 4H), 0.88(t, J=6.9Hz, 3H);
13C NMR(75MHz，CDCl3)δ167.9(d，J＝259.7Hz)，142.7，128.2，127.6，125.5，90.4(d，J＝19.1Hz)，76.6(d，J＝28.3Hz)，38.6，25.4，22.9，14.0； 13 C NMR (75MHz, CDCl 3 ) δ167.9 (d, J=259.7Hz), 142.7, 128.2, 127.6, 125.5, 90.4 (d, J=19.1Hz), 76.6 (d, J=28.3Hz), 38.6 , 25.4, 22.9, 14.0;
19F NMR(288MHz，CDCl3)δ-107.1； 19 F NMR (288MHz, CDCl 3 ) δ-107.1;
IR(neat)v(cm-1)3471，2958，2871，1670，1495，1447，1377，1233，1137；IR (neat) v (cm -1 ) 3471, 2958, 2871, 1670, 1495, 1447, 1377, 1233, 1137;
MS(70eV，EI)m/z(％)：208(M+，7.37)，151(100)；MS (70eV, EI) m/z (%): 208 (M + , 7.37), 151 (100);
HRMS Calcd for C13H17OF(M+)：208.1263，Found：208.1269。HRMS Calcd for C 13 H 17 OF (M + ): 208.1263, Found: 208.1269.
实施例2Example 2
按实施例1所述的方法，不同的是所用底物和试剂为：1-苯基-1，2-丙二烯(58.0mg，0.5mmol)，1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(212.4mg，0.60mmol)，5.0mL MeCN与0.5mL H2O，得产物28.2mg，产率为37％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 1-phenyl-1,2-propadiene (58.0 mg, 0.5 mmol), 1-chloromethyl-4-fluoro-1 , 4-diazabicyclo[2.2.2]octanetetrafluoroborate (Selectfluor) (212.4mg, 0.60mmol), 5.0mL MeCN and 0.5mL H 2 O, the product was 28.2mg, and the yield was 37% . The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.48-7.31(m，5H)，5.22(dd，J＝9.0 & 4.5Hz，1H)，4.82-4.58(m，2H)，2.31(d，J＝4.5Hz，1H)； 1 H NMR (300MHz, CDCl 3 ) δ7.48-7.31(m, 5H), 5.22(dd, J=9.0 & 4.5Hz, 1H), 4.82-4.58(m, 2H), 2.31(d, J=4.5 Hz, 1H);
13C NMR(75MHz，CDCl3)δ165.5(d，J＝258.2Hz)，139.1，128.63，128.57，126.7，91.2(d，J＝17.1Hz)，72.4(d，J＝33.7Hz)； 13 C NMR (75MHz, CDCl 3 ) δ165.5 (d, J=258.2Hz), 139.1, 128.63, 128.57, 126.7, 91.2 (d, J=17.1Hz), 72.4 (d, J=33.7Hz);
19F NMR(288MHz，CDCl3)δ-1 08.5； 19 F NMR (288MHz, CDCl 3 ) δ-1 08.5;
IR(neat)v(cm-1)3376，1677，1495，1456，，1119，1048；IR (neat) v (cm -1 ) 3376, 1677, 1495, 1456, 1119, 1048;
MS(70eV，EI)m/z(％)：152(M+，64.47)，77(100)。MS (70eV, EI) m/z (%): 152 (M + , 64.47), 77 (100).
实施例3Example 3
按实施例1所述的方法，不同的是所用底物和试剂为：3-苯基-1，2-戊二烯(72.0mg，0.5mmol)，1-氯甲基-4-氟-1，-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(212.4mg，0.60mmol)，5.0mL MeCN与0.5mL H2O，得产物56.8mg，产率为65％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 3-phenyl-1,2-pentadiene (72.0 mg, 0.5 mmol), 1-chloromethyl-4-fluoro-1 , -diazabicyclo[2.2.2]octanetetrafluoroborate (Selectfluor) (212.4mg, 0.60mmol), 5.0mL MeCN and 0.5mL H 2 O, the product was 56.8mg, and the yield was 65%. The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.52-7.44(m，2H)，7.42-7.27(m，3H)，4.80(dd，J＝6.0 & 3.3Hz，1H)，4.68(dd，J＝26.7 & 3.3Hz，1H)，2.28(s，1H)，1.87-2.15(m，2H)，0.90(t，J＝7.2Hz，3H)； 1 H NMR (300MHz, CDCl 3 ) δ7.52-7.44(m, 2H), 7.42-7.27(m, 3H), 4.80(dd, J=6.0 & 3.3Hz, 1H), 4.68(dd, J=26.7 & 3.3Hz, 1H), 2.28(s, 1H), 1.87-2.15(m, 2H), 0.90(t, J=7.2Hz, 3H);
13C NMR(75MHz，CDCl3)δ167.7(d，J＝259.7Hz)，142.4，128.2，127.6，125.5，90.59(d，J＝18.8Hz)，76.65，31.55，7.60； 13 C NMR (75MHz, CDCl 3 ) δ167.7 (d, J=259.7Hz), 142.4, 128.2, 127.6, 125.5, 90.59 (d, J=18.8Hz), 76.65, 31.55, 7.60;
19F NMR(288MHz，CDCl3)δ-107.2； 19 F NMR (288MHz, CDCl 3 ) δ-107.2;
IR(neat)v(cm-1)3473，2958，2931，2870，1670，1607，1464，1379，1234，1135；IR (neat) v (cm -1 ) 3473, 2958, 2931, 2870, 1670, 1607, 1464, 1379, 1234, 1135;
MS(70eV，EI)m/z(％)：180(M+，4.21)，73(100)；MS (70eV, EI) m/z (%): 180 (M + , 4.21), 73 (100);
HRMS Calcd for C11H13OF(M+)：180.0950，Found：180.0959。HRMS Calcd for C 11 H 13 OF (M + ): 180.0950, Found: 180.0959.
实施例4Example 4
按实施例1所述的方法，不同的是所用底物和试剂为：3-苯基-1，2-壬二烯(100.0mg，0.5mmol)，1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(212.4mg，0.60mmol)，5.0mL MeCN与0.5mL H2O，得产物67.6mg，产率为57％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 3-phenyl-1,2-nonadiene (100.0 mg, 0.5 mmol), 1-chloromethyl-4-fluoro-1 , 4-diazabicyclo[2.2.2]octanetetrafluoroborate (Selectfluor) (212.4mg, 0.60mmol), 5.0mL MeCN and 0.5mL H 2 O, the product was 67.6mg, and the yield was 57% . The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.50(d，J＝7.5Hz，2H)，7.24-7.39(m，3H)，4.81(dd，J＝7.8 &2.7Hz，1H)，4.70(dd，J＝24.3 & 2.7Hz，1H)，2.25(s，1H)，2.05-1.87(m，2H)，1.48-1.21(m，8H)，0.86(t，J＝6.3Hz，3H)； 1 H NMR (300MHz, CDCl 3 ) δ7.50(d, J=7.5Hz, 2H), 7.24-7.39(m, 3H), 4.81(dd, J=7.8 & 2.7Hz, 1H), 4.70(dd, J=24.3 & 2.7Hz, 1H), 2.25(s, 1H), 2.05-1.87(m, 2H), 1.48-1.21(m, 8H), 0.86(t, J=6.3Hz, 3H);
13C NMR(75MHz，CDCl3)δ167.9(d，J＝259.7Hz)，142.7，128.2，127.6，125.5，90.4(d，J＝18.5Hz)，76.6(d，J＝28.4Hz)，38.8，31.7，29.4，23.2，22.6，14.0； 13 C NMR (75MHz, CDCl 3 ) δ167.9(d, J=259.7Hz), 142.7, 128.2, 127.6, 125.5, 90.4(d, J=18.5Hz), 76.6(d, J=28.4Hz), 38.8 , 31.7, 29.4, 23.2, 22.6, 14.0;
19F NMR(288MHz，CDCl3)δ-107.1； 19 F NMR (288MHz, CDCl 3 ) δ-107.1;
IR(neat)v(cm-1)3580，3472，3063，2928，2958，1670，1597，1486，1451，1376，12301182，1131，1068；IR (neat) v (cm -1 ) 3580, 3472, 3063, 2928, 2958, 1670, 1597, 1486, 1451, 1376, 12301182, 1131, 1068;
MS(70eV，EI)m/z(％)：236(M+，2.70)，151(100)；MS (70eV, EI) m/z (%): 236 (M + , 2.70), 151 (100);
HRMS Calcd for C15H21OF(M+)：236.1576，Found：236.1566。HRMS Calcd for C 15 H 21 OF (M + ): 236.1576, Found: 236.1566.
实施例5Example 5
按实施例1所述的方法，不同的是所用底物和试剂为：1，1-二苯基-1，2-丙二烯(57.6mg，0.3mmol)，1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(127.4mg，0.36mmol)，3.0mL MeCN与0.3mL H2O，得产物33.5mg，产率为49％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 1,1-diphenyl-1,2-propadiene (57.6mg, 0.3mmol), 1-chloromethyl-4- Fluorine-1,4-diazabicyclo[2.2.2]octane tetrafluoroborate (Selectfluor) (127.4mg, 0.36mmol), 3.0mL MeCN and 0.3mL H 2 O, the product was 33.5mg, the yield for 49%. The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.50-7.41(m，4H)，7.40-7.28(m，6H)，4.95(dd，J＝17.4 & 3.0Hz，1H)，4.49(dd，J＝18.9 & 3.0Hz，1H)，2.91(s，1H)； 1 H NMR (300MHz, CDCl 3 ) δ7.50-7.41(m, 4H), 7.40-7.28(m, 6H), 4.95(dd, J=17.4 & 3.0Hz, 1H), 4.49(dd, J=18.9 & 3.0Hz, 1H), 2.91(s, 1H);
13C NMR(75MHz，CDCl3)δ166.9(d，J＝261.3Hz)，142.7，128.2，128.0，127.4，94.2(d，J＝18.8Hz)，79.7(d，J＝27.7Hz)； 13 C NMR (75MHz, CDCl 3 ) δ166.9 (d, J=261.3Hz), 142.7, 128.2, 128.0, 127.4, 94.2 (d, J=18.8Hz), 79.7 (d, J=27.7Hz);
19F NMR(288MHz，CDCl3)δ-104.4； 19 F NMR (288MHz, CDCl 3 ) δ-104.4;
IR(neat)v(cm-1)3582，3459，3061，3030，1669，1597，1492，1449，1365，1335，1235，1168，1135，1031；IR (neat) v (cm -1 ) 3582, 3459, 3061, 3030, 1669, 1597, 1492, 1449, 1365, 1335, 1235, 1168, 1135, 1031;
MS(70eV，EI)m/z(％)：228(M+，8.49)，105(100)；MS (70eV, EI) m/z (%): 228 (M + , 8.49), 105 (100);
HRMS Calcd for C15H13OF(M+)：228.0950，Found：228.0950。HRMS Calcd for C 15 H 13 OF (M + ): 228.0950, Found: 228.0950.
实施例6Example 6
按实施例1所述的方法，不同的是所用底物和试剂为：3-间甲基苯基-1，2-庚二烯(93.0mg，0.5mmol)，1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(212.4mg，0.60mmol)，5.0mL MeCN与0.5mL H2O，得产物81.8mg，产率为74％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 3-m-methylphenyl-1,2-heptadiene (93.0mg, 0.5mmol), 1-chloromethyl-4- Fluorine-1,4-diazabicyclo[2.2.2]octane tetrafluoroborate (Selectfluor) (212.4mg, 0.60mmol), 5.0mL MeCN and 0.5mL H 2 O, the product 81.8mg was obtained, the yield was 74%. The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.32-7.20(m，3H)，7.10(d，J＝6.9Hz，1H)，4.81(dd，J＝9.9 &2.7Hz，1H)，4.69(dd，J＝22.5 & 3.0Hz，1H)，2.36(s，3H)，2.24(s，1H)，2.09-1.87(m，2H)，1.44-1.16(m，4H)，0.88(t，J＝6.9Hz，3H)； 1 H NMR (300MHz, CDCl 3 ) δ7.32-7.20(m, 3H), 7.10(d, J=6.9Hz, 1H), 4.81(dd, J=9.9&2.7Hz, 1H), 4.69(dd, J=22.5 & 3.0Hz, 1H), 2.36(s, 3H), 2.24(s, 1H), 2.09-1.87(m, 2H), 1.44-1.16(m, 4H), 0.88(t, J=6.9Hz ,3H);
13C NMR(75MHz，CDCl3)δ168.0(d，J＝260.0Hz)，142.7，137.9，128.3，128.1，126.1，122.5，90.3(d，J＝18.9Hz)，76.6(d，J＝27.6Hz)，38.6，25.4，22.9，21.6，14.0； 13 C NMR (75MHz, CDCl 3 ) δ168.0(d, J=260.0Hz), 142.7, 137.9, 128.3, 128.1, 126.1, 122.5, 90.3(d, J=18.9Hz), 76.6(d, J=27.6 Hz), 38.6, 25.4, 22.9, 21.6, 14.0;
19F NMR(288MHz，CDCl3)δ-107.0； 19 F NMR (288MHz, CDCl 3 ) δ-107.0;
IR(neat)v(cm-1)3473，3029，2958，2931，2870，1670，1607，1487，1464，1379，1234，1210，1135，1078，1057；IR (neat) v (cm -1 ) 3473, 3029, 2958, 2931, 2870, 1670, 1607, 1487, 1464, 1379, 1234, 1210, 1135, 1078, 1057;
MS(70eV，EI)m/z(％)：222(M+，3.97)，73(100)；MS (70eV, EI) m/z (%): 222 (M + , 3.97), 73 (100);
HRMS Calcd for C14H19OF(M+)：222.1420，Found：222.1421。HRMS Calcd for C 14 H 19 OF (M + ): 222.1420, Found: 222.1421.
实施例7Example 7
按实施例1所述的方法，不同的是所用底物和试剂为：3-间甲基苯基-1，2-壬二烯(107.1mg，0.5mmol)，1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(212.4mg，0.60mmol)，5.0mL MeCN与0.5mL H2O，得产物88.2mg，产率为71％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 3-m-methylphenyl-1,2-nonadiene (107.1 mg, 0.5 mmol), 1-chloromethyl-4- Fluorine-1,4-diazabicyclo[2.2.2]octanetetrafluoroborate (Selectfluor) (212.4mg, 0.60mmol), 5.0mL MeCN and 0.5mL H 2 O, the product 88.2mg was obtained, the yield was 71%. The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.32-7.20(m，3H)，7.09(d，J＝7.2Hz，1H)，4.80(dd，J1＝10.2Hz，J2＝3.0Hz，1H)，4.69(dd，J1＝22.2Hz，J1＝3.0Hz，1H)，2.36(s，3H)，2.27(s，1H)，2.05-1.90(m，2H)，1.44-1.22(m，8H)，0.86(t，J＝6.0Hz，3H)； 1 H NMR (300MHz, CDCl 3 ) δ7.32-7.20 (m, 3H), 7.09 (d, J=7.2Hz, 1H), 4.80 (dd, J 1 =10.2Hz, J 2 =3.0Hz, 1H) , 4.69(dd, J 1 =22.2Hz, J 1 =3.0Hz, 1H), 2.36(s, 3H), 2.27(s, 1H), 2.05-1.90(m, 2H), 1.44-1.22(m, 8H ), 0.86(t, J=6.0Hz, 3H);
13C NMR(75MHz，CDCl3)δ168.0(d，J＝260.0Hz)，142.7，137.8，128.3，128.1，126.1，122.5，90.3(d，J＝18.8Hz)，76.6(d，J＝28.8Hz)，38.8，31.7，29.5，23.2，22.6，21.6，14.0； 13 C NMR (75MHz, CDCl 3 ) δ168.0(d, J=260.0Hz), 142.7, 137.8, 128.3, 128.1, 126.1, 122.5, 90.3(d, J=18.8Hz), 76.6(d, J=28.8 Hz), 38.8, 31.7, 29.5, 23.2, 22.6, 21.6, 14.0;
19F NMR(282MHz，CDCl3)δ-106.9； 19 F NMR (282MHz, CDCl 3 ) δ-106.9;
IR(neat)v(cm-1)3473，3029，2958，2931，2870，1670，1607，1487，1464，1379，1341，1234，1210，1135，1078，1 057；IR (neat) v (cm -1 ) 3473, 3029, 2958, 2931, 2870, 1670, 1607, 1487, 1464, 1379, 1341, 1234, 1210, 1135, 1078, 1057;
MS(70eV，EI)m/z(％)：250(M+，6.23)，165(100)；MS (70eV, EI) m/z (%): 250 (M + , 6.23), 165 (100);
Elemental analysis：Calcd for C16H23FO：C，76.76，H，9.26；Found：C，76.89，H，9.05。Elemental analysis: Calcd for C 16 H 23 FO: C, 76.76, H, 9.26; Found: C, 76.89, H, 9.05.
实施例8Example 8
按实施例1所述的方法，不同的是所用底物和试剂为：3-间三氟甲基苯基-1，2-庚二烯(120.0mg，0.5mmol)，1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(212.4mg，0.60mmol)，5.0mL MeCN与0.5mL H2O，得产物54.8mg，产率为40％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 3-trifluoromethylphenyl-1,2-heptadiene (120.0 mg, 0.5 mmol), 1-chloromethyl- 4-Fluoro-1,4-diazabicyclo[2.2.2]octanetetrafluoroborate (Selectfluor) (212.4mg, 0.60mmol), 5.0mL MeCN and 0.5mL H 2 O, the product 54.8mg was obtained, The yield was 40%. The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.80(s，1H)，7.69(d，J＝7.8Hz，1H)，7.56(d，J＝7.5Hz，1H)，7.48(t，J＝7.8Hz，1H)，4.85(dd，J＝6.6 & 3.3Hz，1H)，4.74(dd，J＝25.8 & 3.3Hz，1H)，2.30(s，1H)，1.87-2.18(m，2H)，1.26-1.44(m，3H)，1.10-1.26(m，1H)，0.89(t，J＝6.9Hz，3H)； 1 H NMR (300MHz, CDCl 3 ) δ7.80(s, 1H), 7.69(d, J=7.8Hz, 1H), 7.56(d, J=7.5Hz, 1H), 7.48(t, J=7.8Hz , 1H), 4.85(dd, J=6.6 & 3.3Hz, 1H), 4.74(dd, J=25.8 & 3.3Hz, 1H), 2.30(s, 1H), 1.87-2.18(m, 2H), 1.26- 1.44(m, 3H), 1.10-1.26(m, 1H), 0.89(t, J=6.9Hz, 3H);
13C NMR(75MHz，CDCl3)δ167.2(d，J＝260.4Hz)，143.9，130.7(q，J＝31.6Hz)，129.0，128.7，125.9，124.5(q，J＝4.1Hz)，122.4(q，J＝4.7Hz)，90.9(d，J＝18.6Hz)，76.2，38.8，25.2(d，J＝8.6Hz)，22.8，13.8(d，J＝9.6Hz)； 13 C NMR (75MHz, CDCl 3 ) δ167.2(d, J=260.4Hz), 143.9, 130.7(q, J=31.6Hz), 129.0, 128.7, 125.9, 124.5(q, J=4.1Hz), 122.4 (q, J=4.7Hz), 90.9(d, J=18.6Hz), 76.2, 38.8, 25.2(d, J=8.6Hz), 22.8, 13.8(d, J=9.6Hz);
19F NMR(288MHz，CDCl3)δ-62.6，-107.6； 19 F NMR (288MHz, CDCl 3 ) δ-62.6, -107.6;
IR(neat)v(cm-1)3475，2961，1672，1442，1330，1167，1129，1076；IR (neat) v (cm -1 ) 3475, 2961, 1672, 1442, 1330, 1167, 1129, 1076;
MS(70eV，EI)m/z(％)：277(M++H，90.0)，237(100)；MS (70eV, EI) m/z (%): 277 (M ++ H, 90.0), 237 (100);
HRMS Calcd for C14H16OF4(M+)：276.1137，Found：276.1134。HRMS Calcd for C 14 H 16 OF 4 (M + ): 276.1137, Found: 276.1134.
实施例9Example 9
按实施例1所述的方法，不同的是所用底物和试剂为：3-对甲基苯基-1，2-庚二烯(93.5mg，0.5mmol)，1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(212.4mg，0.60mmol)，5.0mL MeCN与0.5mL H2O，得产物98.7mg，产率为88％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 3-p-methylphenyl-1,2-heptadiene (93.5mg, 0.5mmol), 1-chloromethyl-4- Fluorine-1,4-diazabicyclo[2.2.2]octane tetrafluoroborate (Selectfluor) (212.4mg, 0.60mmol), 5.0mL MeCN and 0.5mL H 2 O, the product was 98.7mg, the yield was 88%. The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.42(d，J＝8.1Hz，2H)，7.20(d，J＝8.1Hz，2H)，4.83(dd，J＝10.5 & 3.3Hz，1H)，4.69(dd，J＝21.9 & 3.3Hz，1H)，2.37(s，3H)，2.29(s，1H)，2.25-1.89(m，2H)，1.48-1.17(m，4H)，0.92(t，J＝7.2Hz，3H)； 1 H NMR (300MHz, CDCl 3 ) δ7.42 (d, J=8.1Hz, 2H), 7.20 (d, J=8.1Hz, 2H), 4.83 (dd, J=10.5 & 3.3Hz, 1H), 4.69 (dd, J=21.9 & 3.3Hz, 1H), 2.37(s, 3H), 2.29(s, 1H), 2.25-1.89(m, 2H), 1.48-1.17(m, 4H), 0.92(t, J =7.2Hz, 3H);
13C NMR(75MHz，CDCl3)δ167.6(d，J＝260.0Hz)，139.8，137.3，128.9，125.4，90.2(d，J＝18.5Hz)，76.5(d，J＝28.7Hz)，38.5，25.4，22.9，21.0，13.9； 13 C NMR (75MHz, CDCl 3 ) δ167.6 (d, J=260.0Hz), 139.8, 137.3, 128.9, 125.4, 90.2 (d, J=18.5Hz), 76.5 (d, J=28.7Hz), 38.5 , 25.4, 22.9, 21.0, 13.9;
19F NMR(288MHz，CDCl3)δ-107.1； 19 F NMR (288MHz, CDCl 3 ) δ-107.1;
IR(neat)v(cm-1)3477，2958，1670，1464，1380，1235，1115；IR (neat) v (cm -1 ) 3477, 2958, 1670, 1464, 1380, 1235, 1115;
MS(70eV，EI)m/z(％)：222(M+，3.87)，165(100)；MS (70eV, EI) m/z (%): 222 (M + , 3.87), 165 (100);
HRMS Calcd for C14H19OF(M+)：222.1420，Found：222.1424。HRMS Calcd for C 14 H 19 OF (M + ): 222.1420, Found: 222.1424.
实施例10Example 10
按实施例1所述的方法，不同的是所用底物和试剂为：3-对氟苯基-1，2-壬二烯(109.0mg，0.5mmol)，1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(212.4mg，0.60mmol)，5.0mL MeCN与0.5mL H2O，得产物98.5mg，产率为78％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 3-p-fluorophenyl-1,2-nonadiene (109.0mg, 0.5mmol), 1-chloromethyl-4-fluoro -1,4-diazabicyclo[2.2.2]octanetetrafluoroborate (Selectfluor) (212.4mg, 0.60mmol), 5.0mL MeCN and 0.5mL H 2 O, the product was 98.5mg, and the yield was 78%. The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.48(dd，J＝8.7 & 5.7Hz，2H)，7.04(t，J＝8.7Hz，2H)，4.81(dd，J＝6.9 & 3.3Hz，1H)，4.70(dd，J＝25.8 & 3.3Hz，1H)，2.26(s，1H)，2.11-1.85(m，2H)，1.48-1.17(m，8H)，0.87(t，J＝6.6Hz，3H)； 1 H NMR (300MHz, CDCl 3 ) δ7.48(dd, J=8.7 & 5.7Hz, 2H), 7.04(t, J=8.7Hz, 2H), 4.81(dd, J=6.9 & 3.3Hz, 1H) , 4.70(dd, J=25.8 & 3.3Hz, 1H), 2.26(s, 1H), 2.11-1.85(m, 2H), 1.48-1.17(m, 8H), 0.87(t, J=6.6Hz, 3H );
13C NMR(75MHz，CDCl3)δ167.8(d，J＝260.1Hz)，162.2(d，J＝244.6Hz)，138.5(d，J＝2.8Hz)，127.4(d，J＝8.0Hz)，115.0(d，J＝20.6Hz)，90.5(d，J＝18.9Hz)，76.3(d，J＝28.3Hz)，39.0，31.7，29.4，23.2，22.5，14.0； 13 C NMR (75MHz, CDCl 3 ) δ167.8(d, J=260.1Hz), 162.2(d, J=244.6Hz), 138.5(d, J=2.8Hz), 127.4(d, J=8.0Hz) , 115.0(d, J=20.6Hz), 90.5(d, J=18.9Hz), 76.3(d, J=28.3Hz), 39.0, 31.7, 29.4, 23.2, 22.5, 14.0;
19F NMR(288MHz，CDCl3)δ-107.3，-115.2； 19 F NMR (288MHz, CDCl 3 ) δ-107.3, -115.2;
IR(neat)v(cm-1)3473，2967，1671，1509，1233，1162；IR (neat) v (cm -1 ) 3473, 2967, 1671, 1509, 1233, 1162;
MS(70eV，EI)m/z(％)：254(M+，2.03)，169(100)；MS (70eV, EI) m/z (%): 254 (M + , 2.03), 169 (100);
HRMS Calcd for C15H20OF2(M+)：254.1482，Found：254.1483。HRMS Calcd for C 15 H 20 OF 2 (M + ): 254.1482, Found: 254.1483.
实施例11Example 11
按实施例1所述的方法，不同的是所用底物和试剂为：3-邻甲基苯基-1，2-庚二烯(93.1mg，0.5mmol)，1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(212.4mg，0.60mmol)，5.0mL MeCN与0.5mL H2O，得产物49.8mg，产率为45％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 3-o-methylphenyl-1,2-heptadiene (93.1mg, 0.5mmol), 1-chloromethyl-4- Fluorine-1,4-diazabicyclo[2.2.2]octane tetrafluoroborate (Selectfluor) (212.4mg, 0.60mmol), 5.0mL MeCN and 0.5mL H 2 O, the product was 49.8mg, the yield 45%. The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.55-7.47(m，1H)，7.24-7.13(m，3H)，4.81(dd，J＝18.0 & 3.3Hz，1H)，4.66(dd，J＝20.4 & 3.3Hz，1H)，2.50(s，3H)，2.23(s，1H)，2.21-2.00(m，2H)，1.46-1.10(m，4H)，0.90(t，J＝7.2Hz，3H)； 1 H NMR (300MHz, CDCl 3 ) δ7.55-7.47(m, 1H), 7.24-7.13(m, 3H), 4.81(dd, J=18.0 & 3.3Hz, 1H), 4.66(dd, J=20.4 & 3.3Hz, 1H), 2.50(s, 3H), 2.23(s, 1H), 2.21-2.00(m, 2H), 1.46-1.10(m, 4H), 0.90(t, J=7.2Hz, 3H) ;
13C NMR(75MHz，CDCl3)δ168.0(d，J＝260.0Hz)，139.4，136.4，132.5，127.7，127.0，125.6，91.1(d，J＝19.4Hz)，77.5(d，J＝28.2Hz)，37.3，25.6，22.9，21.6，14.0； 13 C NMR (75MHz, CDCl 3 ) δ168.0(d, J=260.0Hz), 139.4, 136.4, 132.5, 127.7, 127.0, 125.6, 91.1(d, J=19.4Hz), 77.5(d, J=28.2 Hz), 37.3, 25.6, 22.9, 21.6, 14.0;
19F NMR(288MHz，CDCl3)δ-106.6； 19 F NMR (288MHz, CDCl 3 ) δ-106.6;
IR(neat)v(cm-1)3477，2959，1669，1458，1234，1124；IR (neat) v (cm -1 ) 3477, 2959, 1669, 1458, 1234, 1124;
MS(70eV，EI)m/z(％)：222(M+，2.19)，165(100)；MS (70eV, EI) m/z (%): 222 (M + , 2.19), 165 (100);
HRMS Calcd for C14H19OF(M+)：222.1420，Found：222.1415。HRMS Calcd for C 14 H 19 OF (M + ): 222.1420, Found: 222.1415.
实施例12Example 12
按实施例1所述的方法，不同的是所用底物和试剂为：3-邻甲基苯基-1，2-壬二烯(106.8mg，0.5mmol)，1-氯甲基-4-氟-1，4-二氮二环[2.2.2]辛烷四氟硼酸盐(Selectfluor)(212.4mg，0.60mmol)，5.0mL MeCN与0.5mL H2O，得产物49.9mg，产率为40％。产物为无色液体。According to the method described in Example 1, the difference is that the substrates and reagents used are: 3-o-methylphenyl-1,2-nonadiene (106.8 mg, 0.5 mmol), 1-chloromethyl-4- Fluorine-1,4-diazabicyclo[2.2.2]octanetetrafluoroborate (Selectfluor) (212.4mg, 0.60mmol), 5.0mL MeCN and 0.5mL H 2 O, the product 49.9mg was obtained, the yield 40%. The product is a colorless liquid.
1H NMR(300MHz，CDCl3)δ7.53-7.46(m，1H)，7.24-7.12(m，3H)，4.80(dd，J1＝18.3Hz，J2＝3.0Hz，1H)，4.65(dd，J1＝20.4Hz，J2＝3.0Hz，1H)，2.49(s，3H)，2.22(s，1H)，2.19-1.99(m，2H)，1.45-1.12(m，8H)，0.86(t，J＝6.3Hz，3H)； 1 H NMR (300MHz, CDCl 3 ) δ7.53-7.46 (m, 1H), 7.24-7.12 (m, 3H), 4.80 (dd, J 1 =18.3Hz, J 2 =3.0Hz, 1H), 4.65 ( dd, J 1 =20.4Hz, J 2 =3.0Hz, 1H), 2.49(s, 3H), 2.22(s, 1H), 2.19-1.99(m, 2H), 1.45-1.12(m, 8H), 0.86 (t, J=6.3Hz, 3H);
13C NMR(75MHz，CDCl3)δ167.4(d，J＝260.3Hz)，139.4，136.4，132.5，127.7，127.0，125.6，91.0(d，J＝18.8Hz)，77.5(d，J＝39.8Hz)，37.6，31.7，29.5，23.4，22.6，21.6，14.0； 13 C NMR (75MHz, CDCl 3 ) δ167.4(d, J=260.3Hz), 139.4, 136.4, 132.5, 127.7, 127.0, 125.6, 91.0(d, J=18.8Hz), 77.5(d, J=39.8 Hz), 37.6, 31.7, 29.5, 23.4, 22.6, 21.6, 14.0;
19F NMR(282MHz，CDCl3)δ-106.5； 19 F NMR (282MHz, CDCl 3 ) δ-106.5;
IR(neat)v(cm-1)3471，2930，2857，1669，1459，1374，1233，1125；IR (neat) v (cm -1 ) 3471, 2930, 2857, 1669, 1459, 1374, 1233, 1125;
MS(70eV，EI)m/z(％)：250(M+，3.92)，165(100)；MS (70eV, EI) m/z (%): 250 (M + , 3.92), 165 (100);
Elemental analysis：Calcd for C16H23FO：C，76.76，H，9.26；Found：C，76.95，H，9.01。Elemental analysis: Calcd for C 16 H 23 FO: C, 76.76, H, 9.26; Found: C, 76.95, H, 9.01.
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| G. Sankar Lal.Site-Selective Fluorination of Organic Compounds Using 1-Alkyl-4-fluoro-1, 4-diazabicyclo[2.2.2]octane Salts(SelectfluorReagents).《Journal of Organic Chemistry》.1993,第58卷(第10期),表II、第2795页左栏倒数第17行-右栏第20行. * |
| Gaj Stavber et al..Selective and Effective Fluorination of Organic Compounds inWater Using Selectfluor F-TEDA-BF4.《Organic Letters》.2004,第6卷(第26期),4973-4976. * |
| M Carmen Pacheco et al..Electrophilic Fluorodesilylation of Allenylmethylsilanes:ANovelEntry to 2-Fluoro-1, 3-dienes.《Organic Letters》.2005,第7卷(第7期),1267-1270. * |
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