CN107337652A - 一种手性噁唑啉钴配合物及用途 - Google Patents

一种手性噁唑啉钴配合物及用途 Download PDF

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CN107337652A
CN107337652A CN201710544145.1A CN201710544145A CN107337652A CN 107337652 A CN107337652 A CN 107337652A CN 201710544145 A CN201710544145 A CN 201710544145A CN 107337652 A CN107337652 A CN 107337652A
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罗梅
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Hefei Xiangchen Chemical Engineering Co Ltd
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
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    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups
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    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0213—Complexes without C-metal linkages
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/16—Copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt
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    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
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    • B01J2531/847—Nickel

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Abstract

一种钴配合物，其化学式如下：

Description

一种手性噁唑啉钴配合物及用途
一、技术领域
本发明涉及一种金属有机配位化合物（配合物）及其制备方法，特别涉及含氮的噁唑啉金属有机配合物及其制备方法，确切地说是一种水杨腈双噁唑啉钴配合物及其合成方法。
二、背景技术
随着有机化学的发展,金属有机化合物在有机合成中的应用愈来愈广,是现在有机化学中极为活跃的领域之一,已经广泛应用于有机合成反应中。20世纪60年代后期出现的使用手性配体与过渡金属络合物催化的不对称合成反应大大加速了手性药物的研究。化学催化不对称合成法的重要内容便是手性配体及含金属催化剂的设计,从而使反应具有高效和高对映选择性。近年来手性双噁唑啉配体一钴金属配合物的合成有许多文献报道。
参考文献：
1. NCN-Pincer Cobalt Complexes Containing Bis(oxazolinyl)phenyl Ligands,
Hosokawa, Satomi; Ito, Jun-ichi; Nishiyama, Hisao, Organometallics(2013), 32(14), 3980-3985;
2. Cyclopentadienyl 1,2- and 1,3-Disubstituted Cobalt Sandwich Compounds{η5-[MeOC(O)]2C5H3} Co(η4-C4Ph4): Precursors for Sterically HinderedBidentate Chiral and Achiral Ligands, Singh, Nem; Elias, Anil J. ,Organometallics (2012), 31(5), 2059-2065;
3.(Py)2Co(CH2SiMe3)2 As an easily accessible source of "CoR2"，Zhu, Di;Janssen, Femke F. B. J.; Budzelaar, Peter H. M. , Organometallics (2010), 29(8), 1897-1908。
三、发明内容
本发明旨在提供一种Co-N金属有机配合物以应用于催化领域，所要解决的技术问题遴选邻羟基噁唑啉作为配体并合成手性双噁唑啉的铜配合物。
本发明所称的手性双噁唑啉的铜配合物一种是由邻羟基苯甲腈、D-苯甘氨醇与六水合氯化钴制备的由以下化学式所示的配合物：
（Ⅰ）。
化学名称：双{2-[4（R）-苯基-4,5-二氢化]-2-噁唑啉基}苯酚钴配合物，简称配合物(I)。该化合物在丙酮酸乙酯的亨利反应及苯甲醛与苯甲酰胺的反应中显示了一定的催化性能，其转化率分别为86 %及99%。
本合成方法包括合成和分离，所述的合成用58.0 mol% 六水合氯化钴做催化剂,邻羟基苯甲腈1.0889gg，D-苯甘氨醇1.8983g，用50mL氯苯做溶剂，回流反应60小时，纯化，即反应结束后脱去氯苯，加入无水乙醇甲醇及三氯甲烷，自然挥发得橙红色晶体配合物。
合成反应如下：
本合成方法一步得到目标产物，工艺简单，操作方便。
四、附图说明
图1双{2-[4（R）-苯基-4,5-二氢化]-2-噁唑啉基}苯酚钴配合物的X-衍射分析图。
五、具体实施方式
在100mL两口瓶中,加入1.2580g（5.310mmol）六水合氯化钴做催化剂, 邻羟基苯甲腈1.0889g (9.15mmol)，D-苯甘氨醇1.8983g，用50mL氯苯做溶剂，回流反应60小时，纯化，即反应结束后脱去氯苯，再加入无水乙醇甲醇及三氯甲烷，自然挥发得橙红色晶体配合物；产率72%, m.p.: 146-147°C, [a]5 D= -149.2°(0.054 , CH3OH), 元素分析：测试值：C:67.87 %, H: 4.86%, N: 6.33 %；计算值：67.54%, 4.53%, N, 6.34%；IR (KBr): 3411,3127，2928, 1614，1617, 1591, 1536, 1493, 1475, 1456, 1439, 1388，1255, 1236，1157, 1074，1056，954，932，913,851, 753，699，660, 615, 567, 530, 415；
配合物晶体数据如下：
经验式 C30H24N2O4Co
分子量 535.44
温度 293(2) K
波长 0.71073 Å
晶系， 空间群 单斜晶系, C2
晶胞参数 a = 19.403(4) Å α = 90 °.
b = 5.6909(11) Å β = 94.438(7)°.
c = 11.562(2) Å γ = 90 °.
体积 1272.9（4）Å^3
电荷密度 2, 1.397 Mg/m^3
吸收 校正参数 0.713 mm^-1
单胞内的电子数目 554
晶体大小 0.160x 0.110x 0.050m
Theta 角的范围 1.767 to 25.497
HKL的指标收集范围 -23<=h<=13, -6<k<6, -13<l<=14
收集/独立衍射数据 3630/ 2284[R(int) = 0.0319]
theta = 30.5的数据完整度 99.9 %
吸收校正的方法 多层扫描
最大最小的透过率 0.7456 and 0.6363
精修使用的方法 F^2 的矩阵最小二乘法
数据数目/使用限制的数目/参数数目 2284/1/168
精修使用的方法 1.002
衍射点的一致性因子 R1 = 0.0547，ωR2= 0.1136
可观察衍射的吻合因子 R1 = 0.0606, ωR2 = 0.1170
绝对构型参数 0.05（2）
差值傅里叶图上的最大峰顶和峰谷 0.575 and -0.265e.Å^-3
晶体典型的键长数据：
Co(1)-O(1) 1.925(4)
Co(1)-O(1)#1 1.925(4)
Co(1)-N(1)#1 1.983(5)
Co(1)-N(1) 1.983(5)
N(1)-C(7) 1.291(7)
N(1)-C(9) 1.475(8)
O(1)-C(1) 1.301(7)
O(2)-C(7) 1.345(7)
O(2)-C(8) 1.439(9)
C(1)-C(2) 1.405(9)
C(1)-C(6) 1.430(10)
C(2)-C(3) 1.366(10)
C(2)-H(2) 0.9300
C(3)-C(4) 1.373(13)
C(3)-H(3) 0.9300
C(4)-C(5) 1.357(12)
C(4)-H(4) 0.9300
C(5)-C(6) 1.414(8)
C(5)-H(5) 0.9300
C(6)-C(7) 1.455(10)
C(8)-C(9) 1.534(9)
C(8)-H(8A) 0.9700
C(8)-H(8B) 0.9700
C(9)-C(10) 1.504(9)
C(9)-H(9) 0.9800
C(10)-C(15) 1.374(9)
C(10)-C(11) 1.376(10)
C(11)-C(12) 1.376(10)
C(11)-H(11) 0.9300
C(12)-C(13) 1.353(14)
C(12)-H(12) 0.9300
C(13)-C(14) 1.353(15)
C(13)-H(13) 0.9300
C(14)-C(15) 1.364(11)
C(14)-H(14) 0.9300
C(15)-H(15) 0.9300
晶体典型的键角数据：
O(1)-Co(1)-O(1)#1 108.4(3)
O(1)-Co(1)-N(1)#1 126.90(18)
O(1)#1-Co(1)-N(1)#1 93.19(18)
O(1)-Co(1)-N(1) 93.19(18)
O(1)#1-Co(1)-N(1) 126.89(18)
N(1)#1-Co(1)-N(1) 111.8(3)
C(7)-N(1)-C(9) 109.6(5)
C(7)-N(1)-Co(1) 123.5(4)
C(9)-N(1)-Co(1) 126.8(4)
C(1)-O(1)-Co(1) 128.1(4)
C(7)-O(2)-C(8) 107.1(5)
O(1)-C(1)-C(2) 119.2(6)
O(1)-C(1)-C(6) 124.7(5)
C(2)-C(1)-C(6) 116.1(6)
C(3)-C(2)-C(1) 122.3(8)
C(3)-C(2)-H(2) 118.9
C(1)-C(2)-H(2) 118.9
C(2)-C(3)-C(4) 121.2(8)
C(2)-C(3)-H(3) 119.4
C(4)-C(3)-H(3) 119.4
C(5)-C(4)-C(3) 119.3(7)
C(5)-C(4)-H(4) 120.3
C(3)-C(4)-H(4) 120.3
C(4)-C(5)-C(6) 121.5(9)
C(4)-C(5)-H(5) 119.3
C(6)-C(5)-H(5) 119.3
C(5)-C(6)-C(1) 119.5(8)
C(5)-C(6)-C(7) 118.9(8)
C(1)-C(6)-C(7) 121.6(5)
N(1)-C(7)-O(2) 115.7(6)
N(1)-C(7)-C(6) 127.9(6)
O(2)-C(7)-C(6) 116.4(6)
O(2)-C(8)-C(9) 105.9(6)
O(2)-C(8)-H(8A) 110.6
C(9)-C(8)-H(8A) 110.6
O(2)-C(8)-H(8B) 110.6
C(9)-C(8)-H(8B) 110.6
H(8A)-C(8)-H(8B) 108.7
N(1)-C(9)-C(10) 113.4(5)
N(1)-C(9)-C(8) 101.8(6)
C(10)-C(9)-C(8) 113.5(5)
N(1)-C(9)-H(9) 109.3
C(10)-C(9)-H(9) 109.3
C(8)-C(9)-H(9) 109.3
C(15)-C(10)-C(11) 117.9(7)
C(15)-C(10)-C(9) 119.6(6)
C(11)-C(10)-C(9) 122.4(7)
C(10)-C(11)-C(12) 120.0(9)
C(10)-C(11)-H(11) 120.0
C(12)-C(11)-H(11) 120.0
C(13)-C(12)-C(11) 121.3(10)
C(13)-C(12)-H(12) 119.4
C(11)-C(12)-H(12) 119.4
C(14)-C(13)-C(12) 118.8(8)
C(14)-C(13)-H(13) 120.6
C(12)-C(13)-H(13) 120.6
C(13)-C(14)-C(15) 121.0(9)
C(13)-C(14)-H(14) 119.5
C(15)-C(14)-H(14) 119.5
C(14)-C(15)-C(10) 120.9(8)
C(14)-C(15)-H(15) 119.5
C(10)-C(15)-H(15) 119.5
六、亨利反应应用
0.0675g 化合物（I），置于25mL烧瓶中，依次加入1mL四氢呋喃、0.3 mL硝基甲烷和0.5mmol丙酮酸乙酯，常温搅拌反应48h，分别取样进行1HNMR检测,其转化率为86%;1 H NMR(CDCl 3 ): δ ) 4.86 (d,J =13.8 Hz, 1H), 4.58 (d, J =13.8 Hz, 1H), 4.34 (m,2H), 3.85(s, 1H), 1.46 (s, 3H), 1.33 (t, J =7.2 Hz, 3H).13 C NMR (CDCl 3 ):δ=173.4, 80.9, 72.4, 63.0, 23.8, 13.9。
七、N，N’-（苯基亚甲基）二苯甲酰胺的制备
在25mL两口瓶中,加入0.0659g配合物I , 2mLTHF和氯苯2mL, 0.05mL苯甲醛及0.1302g苯甲酰胺,回流反应96小时后,有晶体出现：用核磁检测，转化率：99% ; 1HNMR(500MHz, CDCl3, 27℃), δ (ppm) = 9.02 (d，J=7.77Hz, 2H), 7.91 (d, J=7.42Hz,4H),7.54(t，J=7.4Hz,2H),7.47(t,J=7.7Hz,6H),7.37(t,J=7.7Hz,2H),7.30(t, J=7.3Hz,1H), 7.03(t, J=7.9Hz, 1H)。
同时，平行条件下，发明人做了类似配合物的铜（II），镍(III)的催化丙酮酸乙酯的亨利反应及苯甲醛与苯甲酰胺的反应,其结果如下：
（II） (III)
亨利反应应用 II: 58% III:55%
苯甲醛与苯甲酰胺的反应： II: 44% III:79%。

Claims (4)

1.一种钴配合物，其特征在于：由邻羟基苯甲腈、D-苯甘氨醇与六水合氯化钴制备的、由以下化学式所示的配合物：
（Ⅰ）。
2.权利要求1所述的配合物(I)，在293（2）k温度下，在 牛津X-射线单晶衍射仪上，用经石墨单色器单色化的MoKα射线（λ=0.71073 Å）以ω-θ 扫描方式收集衍射数据，其特征在于晶体属斜方晶系, 单斜晶系,C2 ；晶胞参数：a = 19.403(4) Å α = 90 °；b = 5.6909(11)Å β = 94.438(7)°；c = 11.562(2) Å γ = 90 °。
3.权利要求1所述的配合物 (I) 的合成方法，包括合成和分离，所述的合成用58.0mol%六水合氯化钴做催化剂, 邻羟基苯甲腈1.0889g，D-苯甘氨醇1.8983g，用50mL氯苯做溶剂，回流反应60小时，纯化，即反应结束后脱去氯苯，再加入无水乙醇、甲醇及三氯甲烷，自然挥发得橙红色晶体配合物。
4.权利要求1所述的乙酰脲二聚体晶体化合物(Ⅰ)的用途，是作为催化剂在丙酮酸乙酯的亨利反应及苯甲醛与苯甲酰胺的反应中应用，其转化率分别达86%及99%。
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CN110669023A (zh) * 2019-10-17 2020-01-10 合肥工业大学 一种手性噁唑啉铜配合物的用途
CN112480126A (zh) * 2020-12-11 2021-03-12 合肥工业大学 一种5-烷基喹唑啉衍生物的制备及用途

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CN103641787A (zh) * 2013-12-23 2014-03-19 罗梅 一种手性噁唑啉钴配合物及其合成方法
CN105001268A (zh) * 2015-08-13 2015-10-28 合肥祥晨化工有限公司 一种手性噁唑啉铂配合物晶体及其合成方法
CN105198935A (zh) * 2015-10-02 2015-12-30 合肥祥晨化工有限公司 一种手性噁唑啉钯配合物
CN105712927A (zh) * 2016-01-21 2016-06-29 合肥工业大学 一种钴配合物制备及其合成方法
CN106008611A (zh) * 2016-06-03 2016-10-12 合肥工业大学 一种手性钴配合物
CN106220519A (zh) * 2016-07-12 2016-12-14 合肥祥晨化工有限公司 一种钴配合物的制备及合成方法

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CN108191914A (zh) * 2018-01-09 2018-06-22 合肥工业大学 一种锰配合物晶体
CN108840821A (zh) * 2018-04-12 2018-11-20 合肥工业大学 一种钴配合物制备及其合成方法
CN108840821B (zh) * 2018-04-12 2021-05-25 合肥工业大学 一种钴配合物制备及其合成方法
CN110669023A (zh) * 2019-10-17 2020-01-10 合肥工业大学 一种手性噁唑啉铜配合物的用途
CN110669023B (zh) * 2019-10-17 2022-11-29 合肥工业大学 一种手性噁唑啉铜配合物的用途
CN112480126A (zh) * 2020-12-11 2021-03-12 合肥工业大学 一种5-烷基喹唑啉衍生物的制备及用途

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Application publication date: 20171110