CN107383111A - 一种手性镍配合物晶体及用途 - Google Patents

一种手性镍配合物晶体及用途 Download PDF

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CN107383111A
CN107383111A CN201710596855.9A CN201710596855A CN107383111A CN 107383111 A CN107383111 A CN 107383111A CN 201710596855 A CN201710596855 A CN 201710596855A CN 107383111 A CN107383111 A CN 107383111A
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complex
crystal
nickel
phenylalaninol
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罗梅
李名雷
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Hefei Xiangchen Chemical Engineering Co Ltd
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    • 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
    • C07F15/04—Nickel compounds
    • C07F15/045—Nickel compounds without a metal-carbon linkage
    • 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
    • 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
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2217—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
    • C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
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    • 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
    • B01J2531/847—Nickel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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Abstract

一种手性二水合三[R‑(‑)‑苯丙氨醇]硝酸镍配合物镍配合物（I），其化学式如下：

Description

一种手性镍配合物晶体及用途
一、技术领域
本发明涉及一种新化合物及其制备方法，特别涉及一种镍化合物及其制备方法，确切地说是一种二水合三[R-(-)-苯丙氨醇]硝酸镍配合物的制备及合成方法。
二、背景技术
手性氨基醇镍配合物是重要的催化剂和医药化工产品，其作为催化剂在二乙基锌与苯甲醛的加成反应中已显示了较好的催化性能。【1】
参考文献：
1. Catalytic enantioselective conjugate addition of diethylzinc tochalcones using chiral amino alcohol-nickel complexes, Wakimoto, Izumi;Tomioka, Yuko; Kawanami, Yasuhiro , Tetrahedron (2002), 58(40), 8095-8097。
三、发明内容
本发明旨在提供手性二水合三[R-(-)-苯丙氨醇]硝酸镍配合物； 所要解决的技术问题是一步合成得到目标产物。
本发明所称的手性锌配合物是由R-(-)-苯丙氨醇与六水合硝酸镍（Ⅱ）制备的由以下化学式所示的化合物：
(I)。
化学名称：二水合三[R-(-)-苯丙氨醇]硝酸镍配合物,简称配合物(I)。该配合物在苯甲醛与苯甲酰胺的反应中显示了一定的催化性能，其转化率达46%。
本合成方法包括合成和分离，称取D-苯丙氨醇3.0060 g（0.0199mol），六水合硝酸镍1.9271g（0.0066mol）于100mL圆底烧瓶，加入50mL无水甲醇作溶剂，加热搅拌回流36h，热过滤，静置挥发。数天后析出蓝色晶体；用石油醚和正己烷冲洗3次，真空干燥后，得到干净的目标产物。
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是二水合三[R-(-)-苯丙氨醇]硝酸镍配合物的单晶X-衍射图。
五、具体实施方式
二水合三[R-(-)-苯丙氨醇]硝酸镍配合物的制备：
D-苯丙氨醇和六水合硝酸镍以摩尔比3:1比例进行反应，称取D-苯丙氨醇3.0060 g（0.0199mol），六水合硝酸镍1.9271g（0.0066mol）于100mL圆底烧瓶，加入50mL无水甲醇作溶剂，加热搅拌回流36h，热过滤，静置挥发。数天后析出蓝色晶体；用石油醚和正己烷冲洗3次，真空干燥后，得到干净的目标产物，熔点为162～168℃。比旋光度为[α]20 D=-576.87°（c=0.080，CH3OH）。元素分析数据：C27H43N5NiO11，理论值（%）：C：48.23%；H：6.45%；N：10.42%；实测值（%）：C：48.54%；H：6.37%； N：10.57%；红外光谱数据（KBr；υ；cm-1）：3319，3254，2953，2426，1603，1497，1382，1038，828，755，700，669；
配合物的晶体数据：
经验式 C27H43N5O11Ni
分子量 672.37
温度 293(2) K
波长 0.71073 Å
晶系， 空间群 单斜,P212121
晶胞参数 a = 10.0390(10) Å α = 90 °.
b = 13.2501 (12 Å β = 90 °.
c = 25.249(2) Å γ = 120 °.
体积 3358.6（6）Å^3
电荷密度 4, 1.330 Mg/m^3
吸收 校正参数 0.639 mm^-1
单胞内的电子数目 1424
晶体大小 0.220x 0.170x 0.140 mm
Theta 角的范围 1.613 to 25.499°
HKL的指标收集范围 -12<=h<=10, -14<=k<16, -30<=l<=30
收集/独立衍射数据 19413/ 6236 [R(int) = 0.0468]
theta = 30.5的数据完整度 99.9 %
吸收校正的方法 多层扫描
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 6236/61/409
精修使用的方法 1.035
衍射点的一致性因子 R1 = 0.0535，ωR2= 0.1329
可观察衍射的吻合因子 R1 = 0.0747, ωR2 = 0.1463
绝对构型参数 0.023（11）
差值傅里叶图上的最大峰顶和峰谷 0.433and -0.281e.Å^-3
晶体典型的键长数据：
Ni(1)-N(2) 2.045(5)
Ni(1)-N(1) 2.064(5)
Ni(1)-O(2) 2.086(4)
Ni(1)-N(3) 2.094(5)
Ni(1)-O(3) 2.094(4)
Ni(1)-O(1) 2.132(4)
N(1)-C(2) 1.478(7)
N(1)-H(1A) 0.9700
N(1)-H(1B) 0.9700
N(2)-C(11) 1.477(7)
N(2)-H(2A) 0.9700
N(2)-H(2B) 0.9700
N(3)-C(20) 1.490(8)
N(3)-H(3A) 0.9700
N(3)-H(3B) 0.9700
N(4)-O(6) 1.184(9)
N(4)-O(4) 1.190(10)
N(4)-O(5) 1.225(9)
N(5)-O(9) 1.231(8)
N(5)-O(7) 1.233(8)
N(5)-O(8) 1.239(8)
O(1)-C(1) 1.429(8)
O(1)-H(1F) 0.83(3)
O(2)-C(10) 1.440(7)
O(2)-H(2F) 0.81(3)
O(3)-C(19) 1.403(8)
O(3)-H(3F) 0.82(3)
O(10)-H(10D) 0.8337
O(10)-H(10E) 0.8653
O(11)-H(11D) 0.8214
O(11)-H(11E) 0.7436
C(1)-C(2) 1.495(9)
C(1)-H(1C) 0.9700
C(1)-H(1D) 0.9700
C(2)-C(3) 1.522(8)
C(2)-H(2) 0.9800
C(3)-C(4) 1.511(8)
C(3)-H(3C) 0.9700
C(3)-H(3D) 0.9700
C(4)-C(9) 1.384(13)
C(4)-C(5) 1.389(12)
C(5)-C(6) 1.360(12)
C(5)-H(5A) 0.9300
C(6)-C(7) 1.392(17)
C(6)-H(6) 0.9300
C(7)-C(8) 1.351(16)
C(7)-H(7A) 0.9300
C(8)-C(9) 1.425(12)
C(8)-H(8A) 0.9300
C(9)-H(9) 0.9300
C(10)-C(11) 1.494(10)
C(10)-H(10A) 0.9700
C(10)-H(10B) 0.9700
C(11)-C(12) 1.525(7)
C(11)-H(11) 0.9800
C(12)-C(13) 1.491(8)
C(12)-H(12A) 0.9700
C(12)-H(12B) 0.9700
C(13)-C(18) 1.347(13)
C(13)-C(14) 1.371(10)
C(14)-C(15) 1.382(12)
C(14)-H(14) 0.9300
C(15)-C(16) 1.347(16)
C(15)-H(15) 0.9300
C(16)-C(17) 1.378(16)
C(16)-H(16) 0.9300
C(17)-C(18) 1.401(13)
C(17)-H(17) 0.9300
C(18)-H(18) 0.9300
C(19)-C(20) 1.500(9)
C(19)-H(19A) 0.9700
C(19)-H(19B) 0.9700
C(20)-C(21) 1.515(8)
C(20)-H(20) 0.9800
C(21)-C(22) 1.503(9)
C(21)-H(21A) 0.9700
C(21)-H(21B) 0.9700
C(22)-C(23) 1.357(10)
C(22)-C(27) 1.385(10)
C(23)-C(24) 1.387(11)
C(23)-H(23) 0.9300
C(24)-C(25) 1.346(13)
C(24)-H(24) 0.9300
C(25)-C(26) 1.352(13)
C(25)-H(25) 0.9300
C(26)-C(27) 1.393(11)
C(26)-H(26) 0.9300
C(27)-H(27) 0.9300
晶体典型的键角数据：
N(2)-Ni(1)-N(1) 166.54(19)
N(2)-Ni(1)-O(2) 80.86(19)
N(1)-Ni(1)-O(2) 93.6(2)
N(2)-Ni(1)-N(3) 98.7(2)
N(1)-Ni(1)-N(3) 94.1(2)
O(2)-Ni(1)-N(3) 96.46(19)
N(2)-Ni(1)-O(3) 89.84(19)
N(1)-Ni(1)-O(3) 96.4(2)
O(2)-Ni(1)-O(3) 169.78(19)
N(3)-Ni(1)-O(3) 80.69(17)
N(2)-Ni(1)-O(1) 88.2(2)
N(1)-Ni(1)-O(1) 79.42(19)
O(2)-Ni(1)-O(1) 89.47(19)
N(3)-Ni(1)-O(1) 171.5(2)
O(3)-Ni(1)-O(1) 94.49(17)
C(2)-N(1)-Ni(1) 107.3(3)
C(2)-N(1)-H(1A) 110.3
Ni(1)-N(1)-H(1A) 110.3
C(2)-N(1)-H(1B) 110.3
Ni(1)-N(1)-H(1B) 110.3
H(1A)-N(1)-H(1B) 108.5
C(11)-N(2)-Ni(1) 109.3(3)
C(11)-N(2)-H(2A) 109.8
Ni(1)-N(2)-H(2A) 109.8
C(11)-N(2)-H(2B) 109.8
Ni(1)-N(2)-H(2B) 109.8
H(2A)-N(2)-H(2B) 108.3
C(20)-N(3)-Ni(1) 106.2(3)
C(20)-N(3)-H(3A) 110.5
Ni(1)-N(3)-H(3A) 110.5
C(20)-N(3)-H(3B) 110.5
Ni(1)-N(3)-H(3B) 110.5
H(3A)-N(3)-H(3B) 108.7
O(6)-N(4)-O(4) 119.8(9)
O(6)-N(4)-O(5) 121.0(9)
O(4)-N(4)-O(5) 118.8(8)
O(9)-N(5)-O(7) 120.1(7)
O(9)-N(5)-O(8) 120.4(7)
O(7)-N(5)-O(8) 119.3(8)
C(1)-O(1)-Ni(1) 112.1(4)
C(1)-O(1)-H(1F) 116(5)
Ni(1)-O(1)-H(1F) 113(5)
C(10)-O(2)-Ni(1) 110.5(4)
C(10)-O(2)-H(2F) 128(7)
Ni(1)-O(2)-H(2F) 121(7)
C(19)-O(3)-Ni(1) 111.7(4)
C(19)-O(3)-H(3F) 116(4)
Ni(1)-O(3)-H(3F) 114(4)
H(10D)-O(10)-H(10E) 78.3
H(11D)-O(11)-H(11E) 170.7
O(1)-C(1)-C(2) 107.8(5)
O(1)-C(1)-H(1C) 110.1
C(2)-C(1)-H(1C) 110.1
O(1)-C(1)-H(1D) 110.1
C(2)-C(1)-H(1D) 110.1
H(1C)-C(1)-H(1D) 108.5
N(1)-C(2)-C(1) 107.4(5)
N(1)-C(2)-C(3) 112.3(5)
C(1)-C(2)-C(3) 112.9(6)
N(1)-C(2)-H(2) 108.0
C(1)-C(2)-H(2) 108.0
C(3)-C(2)-H(2) 108.0
C(4)-C(3)-C(2) 112.3(5)
C(4)-C(3)-H(3C) 109.1
C(2)-C(3)-H(3C) 109.1
C(4)-C(3)-H(3D) 109.1
C(2)-C(3)-H(3D) 109.1
H(3C)-C(3)-H(3D) 107.9
C(9)-C(4)-C(5) 120.5(8)
C(9)-C(4)-C(3) 121.8(8)
C(5)-C(4)-C(3) 117.7(8)
C(6)-C(5)-C(4) 123.2(12)
C(6)-C(5)-H(5A) 118.4
C(4)-C(5)-H(5A) 118.4
C(5)-C(6)-C(7) 114.1(13)
C(5)-C(6)-H(6) 123.0
C(7)-C(6)-H(6) 123.0
C(8)-C(7)-C(6) 126.9(11)
C(8)-C(7)-H(7A) 116.5
C(6)-C(7)-H(7A) 116.5
C(7)-C(8)-C(9) 116.9(12)
C(7)-C(8)-H(8A) 121.5
C(9)-C(8)-H(8A) 121.5
C(4)-C(9)-C(8) 118.2(12)
C(4)-C(9)-H(9) 120.9
C(8)-C(9)-H(9) 120.9
O(2)-C(10)-C(11) 106.9(5)
O(2)-C(10)-H(10A) 110.3
C(11)-C(10)-H(10A) 110.3
O(2)-C(10)-H(10B) 110.3
C(11)-C(10)-H(10B) 110.3
H(10A)-C(10)-H(10B) 108.6
N(2)-C(11)-C(10) 107.2(5)
N(2)-C(11)-C(12) 112.3(5)
C(10)-C(11)-C(12) 112.9(6)
N(2)-C(11)-H(11) 108.1
C(10)-C(11)-H(11) 108.1
C(12)-C(11)-H(11) 108.1
C(13)-C(12)-C(11) 114.4(5)
C(13)-C(12)-H(12A) 108.7
C(11)-C(12)-H(12A) 108.7
C(13)-C(12)-H(12B) 108.7
C(11)-C(12)-H(12B) 108.7
H(12A)-C(12)-H(12B) 107.6
C(18)-C(13)-C(14) 119.3(7)
C(18)-C(13)-C(12) 118.7(7)
C(14)-C(13)-C(12) 121.8(6)
C(13)-C(14)-C(15) 122.8(9)
C(13)-C(14)-H(14) 118.6
C(15)-C(14)-H(14) 118.6
C(16)-C(15)-C(14) 116.6(11)
C(16)-C(15)-H(15) 121.7
C(14)-C(15)-H(15) 121.7
C(15)-C(16)-C(17) 122.5(11)
C(15)-C(16)-H(16) 118.8
C(17)-C(16)-H(16) 118.8
C(16)-C(17)-C(18) 118.9(12)
C(16)-C(17)-H(17) 120.5
C(18)-C(17)-H(17) 120.5
C(13)-C(18)-C(17) 119.4(11)
C(13)-C(18)-H(18) 120.3
C(17)-C(18)-H(18) 120.3
O(3)-C(19)-C(20) 111.7(6)
O(3)-C(19)-H(19A) 109.3
C(20)-C(19)-H(19A) 109.3
O(3)-C(19)-H(19B) 109.3
C(20)-C(19)-H(19B) 109.3
H(19A)-C(19)-H(19B) 107.9
N(3)-C(20)-C(19) 106.7(5)
N(3)-C(20)-C(21) 113.9(5)
C(19)-C(20)-C(21) 113.2(6)
N(3)-C(20)-H(20) 107.6
C(19)-C(20)-H(20) 107.6
C(21)-C(20)-H(20) 107.6
C(22)-C(21)-C(20) 114.2(5)
C(22)-C(21)-H(21A) 108.7
C(20)-C(21)-H(21A) 108.7
C(22)-C(21)-H(21B) 108.7
C(20)-C(21)-H(21B) 108.7
H(21A)-C(21)-H(21B) 107.6
C(23)-C(22)-C(27) 116.7(7)
C(23)-C(22)-C(21) 122.7(7)
C(27)-C(22)-C(21) 120.6(6)
C(22)-C(23)-C(24) 121.7(8)
C(22)-C(23)-H(23) 119.2
C(24)-C(23)-H(23) 119.2
C(25)-C(24)-C(23) 120.2(9)
C(25)-C(24)-H(24) 119.9
C(23)-C(24)-H(24) 119.9
C(24)-C(25)-C(26) 120.5(9)
C(24)-C(25)-H(25) 119.7
C(26)-C(25)-H(25) 119.7
C(25)-C(26)-C(27) 118.9(9)
C(25)-C(26)-H(26) 120.6
C(27)-C(26)-H(26) 120.6
C(22)-C(27)-C(26) 121.9(8)
C(22)-C(27)-H(27) 119.1
C(26)-C(27)-H(27) 119.1
N，N’-（苯基亚甲基）二苯甲酰胺的制备
在25mL两口瓶中,加入15mol% 配合物I , 氯苯10mL, 0.1mL苯甲醛及0.2034g苯甲酰胺,回流反应21小时后,有晶体出现; 用核磁检测，转化率：46% ; 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)。

Claims (4)

1.一种手性二水合三[R-(-)-苯丙氨醇]硝酸镍配合物镍配合物（I），其化学式如下：
（I）。
2.权利要求1所述的配合物晶体(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MoKa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 单斜, P212121 ；晶胞参数 ： a = 10.0390(10) Å α = 90 °.；b = 13.2501(12 Å β = 90 °；c = 25.249(2) Å γ = 120 °。
3.权利要求2所述的配合物晶体(I)的合成方法，包括合成和分离，其特征在于所述的合成称取D-苯丙氨醇3.0060 g（0.0199mol），六水合硝酸镍1.9271g（0.0066mol）于100mL圆底烧瓶，加入50mL无水甲醇作溶剂，加热搅拌回流36h，热过滤，静置挥发。数天后析出蓝色晶体。
4.权利要求2所述的配合物晶体(I)，该配合物在苯甲醛与苯甲酰胺的反应中显示了一定的催化性能，其转化率达46%。
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