CN106632497A - Carborane derivative crystal built by alkynol ligand and preparation method thereof - Google Patents
Carborane derivative crystal built by alkynol ligand and preparation method thereof Download PDFInfo
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- CN106632497A CN106632497A CN201611112348.5A CN201611112348A CN106632497A CN 106632497 A CN106632497 A CN 106632497A CN 201611112348 A CN201611112348 A CN 201611112348A CN 106632497 A CN106632497 A CN 106632497A
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- alkynol
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- 239000013078 crystal Substances 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003446 ligand Substances 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 53
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 32
- 239000003208 petroleum Substances 0.000 claims description 16
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000003480 eluent Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 6
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 claims description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229960001866 silicon dioxide Drugs 0.000 claims description 5
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- YTZKOQUCBOVLHL-UHFFFAOYSA-N p-methylisopropylbenzene Natural products CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000013461 design Methods 0.000 abstract description 2
- 238000005481 NMR spectroscopy Methods 0.000 abstract 1
- 238000002441 X-ray diffraction Methods 0.000 abstract 1
- GKPOMITUDGXOSB-UHFFFAOYSA-N but-3-yn-2-ol Chemical compound CC(O)C#C GKPOMITUDGXOSB-UHFFFAOYSA-N 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000005564 crystal structure determination Methods 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- -1 organometallic ruthenium compound Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
The invention relates to a carborane derivative crystal built by alkynol ligand and a preparation method thereof, and belongs to the technical field of organic metallochemistry. The structure of the compound is expressed by methods of monocrystal X-ray diffraction and nuclear magnetic resonance and the like and is confirmed; the crystal belongs to a triclinic system; the space group is P-1; the molecular formula is C20H34B10ORuS2; the molecular weight is 563.76; according to the cell parameters, a is 8.4121(5) angstrom; b is 10.8419(7) angstrom; c is 15.3551(9)A; alpha is 91.5940(10) degrees; beta is 95.4510(10) degrees; gamma is 108.3700(10) degrees. According to the method, CH2Cl2is used as a solvent, [p-(CH3)2CHC6H4(CH3)]Ru(S2C2B10H10)] and 3-Butyn-2-ol are used as raw materials to prepare an organic metal compound (the molecular formula is shown as the accompanying drawing). The compound provided by the invention has the characteristics that the preparation method is simple; the yield is high; the repeatability is high, and the like. A novel idea is provided for the design and the synthesis of the carborane derivative with good performance and application prospects.
Description
Technical field
The invention belongs to organometallic chemistry technical field, and in particular to the carborane derivative that a kind of alkynol part is constructed is brilliant
Body and preparation method thereof.
Background technology
16 electronics elemental carbon containing sulfur family borine organo-metallic compounds can be with stable existence, and such compound is by center gold
Category, sulphur, five yuan of metallic heterocyclic planes of carbon atom composition are " Solarium lycopersicoide " structures, and the unsaturation of central metal atom
Property, thus various addition reactions can occur and form the more stable complex with 18 electronic structures.(such as：Hu J R,
Tang X, Liu G F, et al.J.Organomet.Chem.2012,721-722,36；Meng X, Wang F S, Jin G
X.Coord.Chem.Rev., 2010,254,1260；Hu J R, Wen J L, Wu D H, et al.Organometallics,
2011,30,298；Xie Z.Coord.Chem.Rev., 2006,250,259.)
The reaction of half sandwich type elemental carbon containing sulfur family borine organo-metallic compound and alkynes can promote on carborane with carbon
The activation of adjacent boron atom, the functionalization for carborane provides effective approach.In recent years, based on the knot that carborane is unique
Structure property, the research as the borine organo-metallic compound of elemental carbon containing sulfur family of multi-crossed disciplines is just causing more and more science
The great interest of family.(such as：Hu J R, Liu G F, Jiang Q B, et al.Inorg.Chem., 2010,49,11199；Xu
B H, Tao J C, Li Y Z, et al.Organometallics, 2008,27,334；Hu J R, Peng H N, Hu X, et
Al.Acta Chim.Sinica, 2013,71,892；Yao Z J, Jin G X.Coord.Chem.Rev., 2013,257,
2522；Deng L, Xie Z.Coord.Chem.Rev., 2007,251,2452.).The invention discloses a kind of alkynol part structure
Carborane derivative crystal built and preparation method thereof, is that design carborane of the synthesis with superperformance and application prospect derives
Thing provides new thinking.
The content of the invention
It is an object of the invention to disclose carborane derivative crystal that a kind of alkynol part is constructed and preparation method thereof.
For achieving the above object, the technical solution used in the present invention is as follows：
The carborane derivative crystal that the alkynol part of the present invention is constructed is the crystal of following chemical formula：[p-(CH3)2CHC6H4(CH3)]Ru(S2C2B10H9)(CH3CH=CCH2OCH(CH3)C≡CH)；Its skeleton symbol is as follows：
The compound crystal belongs to anorthic system, space group P-1, molecular formula C20H34B10ORuS2, molecular weight=563.76,
Cell parameter：α=91.5940 (10) °, β=95.4510
(10) °, γ=108.3700 (10) °,Z=2, R1=0.0474, wR2=0.1277.
The basic structure of the compound is that a molecule 3- butyne-2-alcohols are inserted into [p- (CH3)2CHC6H4(CH3)]Ru
(S2C2B10H10) in a Ru-S key in, cause [p- (the CH of the intermediate containing Ru-B keys3)2CHC6H4(CH3)]Ru
(S2C2B10H9)(CH3CH=CCH2OH formation), the intermediate forms target with another molecule 3- butyne-2-alcohols dehydrating condensation
Compound [p- (CH3)2CHC6H4(CH3)]Ru(S2C2B10H9)(CH3CH=CCH2OCH(CH3)C≡CH)；Wrap in compound structure
Quaternary metallic heterocyclic RuBCS of hexa-atomic metallic heterocyclic RuSCCSC containing a distortion and close plane；The C=C double bond keys of coordination
It is a length ofBetween traditional carbon-carbon single bondAnd double bondBetween, this bond distance's feature shows double bond
To the significant antibonding contribution of metal center；The bond distance of the keys of end C ≡ C tri- is
Under argon gas protection, by compound [p- (CH3)2CHC6H4(CH3)]Ru(S2C2B10H10)] it is dissolved in 15mL
CH2Cl2In, after stirring and dissolving, add HC ≡ CCH (OH) CH3, 25-30 DEG C of temperature control, stirring reaction 18-20 hour, by reactant liquor
It is concentrated to dryness；Petroleum ether is eluant, eluent with the mixed liquor of dichloromethane, crosses the isolated target chemical combination of 200-300 mesh silicagel columns
Thing；Crystallized with the mixed solvent of dichloromethane with petroleum ether, obtained yellow bulk crystals.
Described [p- (CH3)2CHC6H4(CH3)]Ru(S2C2B10H10)] and HC ≡ CCH (OH) CH3Mol ratio be 1: 2.
Described eluant, eluent is formed by petroleum ether and dichloromethane by 1: 3 volume ratio mixture.
The mixed solvent that described crystallization is used is formed by petroleum ether and dichloromethane by 1: 1 volume ratio mixture.
Beneficial effects of the present invention：
1st, the present invention selects cheap end alkynol HC ≡ CCH (OH) CH3For organic source, its hydroxyl is one more active anti-
Site is answered, the reaction pattern of such boronation has further been expanded, the synthesis and exploitation for the new material containing carborane is provided
New thinking.
2nd, the synthetic method that the present invention represents, low cost, reaction condition are gentle, preparation method is simple, favorable repeatability.
Description of the drawings
Fig. 1 is the compounds of this invention crystal [p- (CH3)2CHC6H4(CH3)]Ru(S2C2B10H9)(CH3CH=CCH2OCH
(CH3) C ≡ CH) and molecular structure ellipsoid figure (30% index ellipsoid, hydrogen atom omit).
Specific embodiment
The compound crystal of the present invention belongs to anorthic system, space group P-1, molecular formula C20H34B10ORuS2, molecular weight=
563.76, cell parameter：α=91.5940
(10) °, β=95.4510 (10) °, γ=108.3700 (10) °,Z=2, R1=0.0474, wR2=
0.1277.Its basic structure be to maintain the ruthenium atom of 6e neutral ligand p -Methylisopropylbenzene bases and sulphur atom, one
Boron atom and the coordination of C=C double bond, cause hexa-atomic metallic heterocyclic RuSCCSC comprising a distortion in compound structure and
Quaternary metallic heterocyclic RuBCS of one close plane；The C=C double bond bond distances of coordination areBetween traditional carbon-carbon single bondAnd double bondBetween, this bond distance's feature shows double bond to the significant antibonding contribution of metal center；End C
The bond distance of the keys of ≡ C tri- is
In the preparation method of the compound crystal of the present invention, under argon gas protection, by compound [p- (CH3)2CHC6H4
(CH3)]Ru(S2C2B10H10)] it is dissolved in 15mL CH2Cl2In, after stirring and dissolving, add HC ≡ CCH (OH) CH3, temperature control 25-30
DEG C, stirring reaction 18-20 hour is concentrated to dryness reactant liquor；Petroleum ether is eluant, eluent with the mixed liquor of dichloromethane, crosses 200-
The isolated target compound of 300 mesh silicagel columns；Crystallized with the mixed solvent of dichloromethane with petroleum ether, obtained yellow block
Crystal.
Embodiment 1
Under argon gas protection, by compound [p- (CH3)2CHC6H4(CH3)]Ru(S2C2B10H10)] (88.4mg, 0.2mmol)
It is dissolved in 15mL CH2Cl2In, after stirring and dissolving, add HC ≡ CCH (OH) CH3(28mg, 0.4mmol), 25 DEG C of temperature control, stirring
Reaction 20 hours, reactant liquor is concentrated to dryness；Cross the isolated target compound of 200-300 mesh silicagel columns (43.9mg, 39%)
(eluant, eluent：V (petroleum ether)/V (dichloromethane)=1: 3)；The compound is dissolved in into petroleum ether molten with the mixing of dichloromethane
(V (petroleum ether)/V (dichloromethane)=1: 1) is crystallized in agent, yellow bulk crystals are obtained.Fusing point：171℃；1H NMR
(CDCl3)：(d, J=7.0Hz, 3H, the CH (CH of δ 1.27,1.293)2), 1.42 (d, J=7.0Hz, 3H, RuCH (CH3)), 2.04
(d, J=7.0Hz, 3H, OCH (CH3)), 2.22 (s, 3H, C6H4-CH3), 2.41 (s, 1H, C ≡ CH), 2.81 (sept.J=
7.0Hz, 1H, CH (CH3)2), 3.02 (d, J=10Hz, 1H, O-CH2), 4.23 (d, J=10Hz, 1H, O-CH2), 4.28 (m,
1H, O-CH), 4.64 (m, 1H, Ru-CH), 5.48 (d, J=6.0Hz, 1H, C6H4), 5.50 (d, J=6.0Hz, 1H, C6H4),
6.24 (d, J=6.0Hz, 1H, C6H4), 6.31 (d, J=6.0Hz, 1H, C6H4).
Embodiment 2
Under argon gas protection, by compound [p- (CH3)2CHC6H4(CH3)]Ru(S2C2B10H10)] (88.4mg, 0.2mmol)
It is dissolved in 15mL CH2Cl2In, after stirring and dissolving, add HC ≡ CCH (OH) CH3(28mg, 0.4mmol), 30 DEG C of temperature control, stirring
Reaction 18 hours, reactant liquor is concentrated to dryness；Cross the isolated target compound of 200-300 mesh silicagel columns (42.8mg, 38%)
(eluant, eluent：V (petroleum ether)/V (dichloromethane)=1: 3)；The compound is dissolved in into petroleum ether molten with the mixing of dichloromethane
(V (petroleum ether)/V (dichloromethane)=1: 1) is crystallized in agent, yellow bulk crystals are obtained.Fusing point：171℃；1H NMR
(CDCl3)：(d, J=7.0Hz, 3H, the CH (CH of δ 1.27,1.293)2), 1.42 (d, J=7.0Hz, 3H, RuCH (CH3)), 2.04
(d, J=7.0Hz, 3H, OCH (CH3)), 2.22 (s, 3H, C6H4-CH3), 2.41 (s, 1H, C ≡ CH), 2.81 (sept.J=
7.0Hz, 1H, CH (CH3)2), 3.02 (d, J=10Hz, 1H, O-CH2), 4.23 (d, J=10Hz, 1H, O-CH2), 4.28 (m,
1H, O-CH), 4.64 (m, 1H, Ru-CH), 5.48 (d, J=6.0Hz, 1H, C6H4), 5.50 (d, J=6.0Hz, 1H, C6H4),
6.24 (d, J=6.0Hz, 1H, C6H4), 6.31 (d, J=6.0Hz, 1H, C6H4).
A kind of further characterization of the organometallic ruthenium compound crystal rich in boron of the gained of Example 1, its process is as follows：
The crystal structure determination of compound：Choosing the monocrystalline of suitable size, to be placed in Bruker SMARTAPEX II CCD mono-
On brilliant diffractometer, with graphite monochromatised Mo K alpha raysFor light source, at a temperature of 293 (2) K, with ω/2 θ
Scan mode collects diffraction data.Data convert is carried out with SAINT programs, and carries out absorption correction with SADABS programs. chemical combination
The structure of thing is solved with direct method, and complete matrix least square method essence is carried out to non-hydrogen atom coordinate and anisotropic temperature factor
Repair.Geometry is hydrogenated with.Structure elucidation adopts SHELXS-97, structure refinement to adopt SHELXL-97.Detailed axonometry data are shown in
Table 1；Important bond distance and bond angle data is shown in Table 2；Crystal structure is shown in accompanying drawing.
Can be seen by above-mentioned characterization result, compound crystal of the present invention belongs to anorthic system, space group P-1, molecule
Formula C20H34B10ORuS2, molecular weight=563.76, cell parameter：
α=91.5940 (10) °, β=95.4510 (10) °, γ=108.3700 (10) °,Z=2, R1=
0.0474, wR2=0.1277.Its basic structure is to maintain the ruthenium atom of 6e neutral ligand p -Methylisopropylbenzene bases and one
Sulphur atom, a boron atom and a C=C double bonds coordination, cause the hexa-atomic metal comprising a distortion in compound structure miscellaneous
Quaternary metallic heterocyclic RuBCS of ring RuSCCSC and a close plane；The C=C double bond bond distances of coordination areBetween
Traditional carbon-carbon single bondAnd double bondBetween, this bond distance's feature shows that double bond is significantly anti-to metal center
Key is contributed；The bond distance of the keys of end C ≡ C tri- is
Above example is merely to illustrate present disclosure, and in addition, the present invention also has other embodiment.But
It is that the technical scheme that all employing equivalents or equivalent deformation mode are formed is all fallen within protection scope of the present invention.
The predominant crystal data of the compound of table 1
The main bond distance of the compound of table 2With bond angle (°)
Claims (6)
1. the carborane derivative crystal that a kind of alkynol part is constructed, it is characterised in that：Compound crystal belongs to anorthic system, space
Group P-1, cell parameter：α=91.5940 (10) °, β=
95.4510 (10) °, γ=108.3700 (10) °,Z=2, R1=0.0474, wR2=0.1277；Point
Minor is C20H34B10ORuS2, molecular weight is 563.76, and skeleton symbol is as follows
2. the carborane derivative crystal that a kind of alkynol part as claimed in claim 1 is constructed, it is characterised in that：Remain 6e
The ruthenium atom of neutral ligand p -Methylisopropylbenzene base and a sulphur atom, a boron atom and a C=C double bonds coordination, lead
Cause the quaternary metallic heterocyclic comprising hexa-atomic metallic heterocyclic RuSCCSC for distorting and a close plane in compound structure
RuBCS；The C=C double bond bond distances of coordination areBetween traditional carbon-carbon single bondAnd double bondBetween,
This bond distance's feature shows double bond to the significant antibonding contribution of metal center；The bond distance of the keys of end C ≡ C tri- is
3. the preparation method of the carborane derivative crystal that a kind of alkynol part as claimed in claim 1 is constructed, its feature exists
In：Under argon gas protection, by compound [p- (CH3)2CHC6H4(CH3)]Ru(S2C2B10H10)] it is dissolved in 15mL CH2Cl2In,
After stirring and dissolving, HC ≡ CCH (OH) CH are added3, 25-30 DEG C of temperature control, stirring reaction 18-20 hour is concentrated to dryness reactant liquor；
Petroleum ether is eluant, eluent with the mixed liquor of dichloromethane, crosses the isolated target compound of 200-300 mesh silicagel columns；Use petroleum ether
Crystallized with the mixed solvent of dichloromethane, obtained yellow bulk crystals.
4. the preparation method of the carborane derivative crystal that a kind of alkynol part as claimed in claim 3 is constructed, its feature exists
In：Described [p- (CH3)2CHC6H4(CH3)]Ru(S2C2B10H10)] and HC ≡ CCH (OH) CH3Mol ratio be 1: 2.
5. the preparation method of the carborane derivative crystal that a kind of alkynol part as claimed in claim 3 is constructed, its feature exists
In：Described eluant, eluent is formed by petroleum ether and dichloromethane by 1: 3 volume ratio mixture.
6. the preparation method of the carborane derivative crystal that a kind of alkynol part as claimed in claim 3 is constructed, its feature exists
In：The used mixed solvent of crystallization is formed by petroleum ether and dichloromethane by 1: 1 volume ratio mixture.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110105404A (en) * | 2019-05-07 | 2019-08-09 | 上海应用技术大学 | The ruthenium complex of the benzoxazoles structure of carborane radical containing ortho position and its preparation and application |
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| CN103951712A (en) * | 2014-04-21 | 2014-07-30 | 上饶师范学院 | Metal ruthenium complex crystal based on activation of boron-hydrogen bonds and preparation method thereof |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103951712A (en) * | 2014-04-21 | 2014-07-30 | 上饶师范学院 | Metal ruthenium complex crystal based on activation of boron-hydrogen bonds and preparation method thereof |
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| 胡久荣: "含硫族碳硼烷配体有机金属钌化合物的合成及其与炔醇的反应性研究", 《中国博士学位论文全文数据库-工程科技Ⅰ辑》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110105404A (en) * | 2019-05-07 | 2019-08-09 | 上海应用技术大学 | The ruthenium complex of the benzoxazoles structure of carborane radical containing ortho position and its preparation and application |
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Application publication date: 20170510 |