CN114621295B - 一种手性噁唑啉钯配合物晶体及用途 - Google Patents

一种手性噁唑啉钯配合物晶体及用途 Download PDF

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CN114621295B
CN114621295B CN202210290030.5A CN202210290030A CN114621295B CN 114621295 B CN114621295 B CN 114621295B CN 202210290030 A CN202210290030 A CN 202210290030A CN 114621295 B CN114621295 B CN 114621295B
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罗梅
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Abstract

一种手性钯配合物，其化学式如下：(Ⅰ)。该手性配合物(I)的合成方法是由1，4‑二氰基苯39.2mmol和D‑苯丙氨醇16.2075g在无水无氧条件下和催化剂无水ZnCl2于氯苯溶剂中回流反应60小时，然后分离、纯化，反应结束后脱去氯苯，将粗产品用石油醚/二氯甲烷按体积比4:1柱层析,得白色噁唑啉晶体；再按照噁唑啉与氯化钯按质量比：1.42：1.70，以氯苯为溶剂反应，用二氯甲烷及无水甲醇进行重结晶，得红褐色双核氯化钯配合物单晶；该手性配合物(I)的用途，其特征在于：作为催化剂在二苯甲酮腙与三甲基硅腈的反应中显示了较好的催化效果，其转化率达74％。

Description

一种手性噁唑啉钯配合物晶体及用途
一、技术领域
本发明涉及一种金属有机配位化合物(配合物)的用途，特别涉及含氮的手性金属有机配合物的用途，确切地说是一种手性噁唑啉钯金属有机配合物及用途。
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及医药领域中的应用愈来愈广,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发展，近年来手性噁唑啉钯金属配合物在有机反应及抗癌等活性中取得了较好的应用。
参考文献：
1 G.C.Hargaden,P.J.Guiry,Chem.Rev.2009,109,2505.
2 G.Desimoni,G.Faita,K.A.Chem.Rev.2006,106,3561.
3.G.Desimoni,G.Faita,K.A.Chem.Rev.2011,111,PR284.
三、发明内容
本发明旨在提供一种Pd-N金属有机配合物以应用于医药领域，所要解决的技术问题是合成手性催化剂并应用于抗癌试剂的研发。
本发明所称的手性钯氮配合物是由以下化学式(I)所示的配合物：
化学名称：：双{[1,4-(4S)-二苄基－2－噁唑啉基苯]氯化钯}配合物，简称配合物(I)。
本手性配合物(I)的合成方法包括反应、分离和纯化，其特征是由1，4-二氰基苯39.2mmol和D-苯丙氨醇16.2075g在无水无氧条件下和催化剂无水ZnCl2(26.4mol％)于氯苯溶剂中回流反应60小时，然后分离、纯化，反应结束后脱去氯苯，将粗产品用石油醚/二氯甲烷(4:1)柱层析,得白色噁唑啉晶体,再按照噁唑啉与氯化钯摩尔比0.7：1，以氯苯为溶剂反应，用三氯甲烷及乙醇进行重结晶，得红褐色双核氯化钯配合物单晶。该手性钯配合物在二苯甲酮腙与三甲基硅腈的反应中显示了较好的催化效果，其转化率达74％。
四、附图说明
图1是配合物(I)的单晶衍射图。
五、具体实施方式
1.手性配合物的制备
(1)[1,4-(4R)-二苄基－2－噁唑啉基]苯的制备
在100mL两口瓶中,无水无氧条件下,加入无水ZnCl21.54g(10.64mmol),40ml氯苯,1,4-二氰基苯5.62g(39.2mmol),D-苯丙氨醇18.8g,将混合物在高温下回流60h,停止反应,减压以除去溶剂,,将剩余物用水溶解,并用CHCl3(20mLx2)萃取,有机相用无水硫酸钠干燥,旋转除去溶剂,将粗产品用石油醚/二氯甲烷(4:1)柱层析,得浅绿色粘稠状液体,产率52％；白色晶体,熔点:48-50℃；[α]25 D＝+39.1°(c 0.098,CHCl3)；1H NMR(500MHz,298K,CDCl3)δppm 7.98(s,4H),7.22-7.32(m,10H,ArH),4.59-4.61(m,2H,CH×2),4.37(t,J＝8.9Hz,2H,CH×2),4.16(t,J＝7.9Hz,2H,CH×2),3.23,3.26(dd,J＝5.1,5.1Hz,2H,CH×2),2.71,2.75(dd,J＝9.0,9.0Hz,2H,CH2×2)；13C{1H}NMR(125MHz,298K,CDCl3)163.4,137.8,130.2,129.2,128.6,128.2,126.6,72.0,68.0,41.8；HRMS(EI)m/z(％)calcd forC26H24N2O2 396.1838；found 396.1833.νmax(cm-1)3420,3081,3054,3031,2988,2956,2893,2231,1647,1608,1497,1454,1406,1359,1343,1317,1293,1276,1262,1201,1174,1073,1046,1017,967,953,860,840,755,697,669,548,527；
双{[1,4-(4R)-二苄基－2－噁唑啉基苯]氯化钯}配合物的制备100mL两口瓶中,无水无氧条件下,加入氯化钯1.7000g(4.92mmol),1,4-(4R)
-二苄基－2－噁唑啉基苯1.4283g，氯苯100mL将混合物在高温下回流48h,停止反应,减压以除去溶剂,,将剩余物三氯甲烷及乙醇溶解，自然挥发，得红褐色配合物得晶体，产率：95％；m.p.:>200℃,[a]5 D＝+16.4°(c 0.0076,CH3OH)；
1H NMR(600MHz,CDCl3),δppm 9.2(s,8H,ArH),7.26-7.44(m,20H，ArH)),4.91-4.93(m,4H),4.67-4.73(m，8H),3.85-3.86(m,4H),3.23-3.27(m,4H)；
13C NMR(150MHz,CDCl3)δppm 165.9(x4),136.5(x4),130.3(x6),129.3(x6),129.2(x6),129.1(x4),127.3(x4),72.9(x4),68.8(x4),67.0(x4),41.5(x4)；νmax(cm-1)3459,3063,3042,3027,3002,2945,2934,2921,2851,1648,1633,1607,1566,1507,1494,1474,1454,1439,1417,1369,1302,1282,1246,1289,2957,2929,2872,1642,1609,1572,1509,1480,1464,1416,1379,1331,1288,1246,1241,1205,1179,1154,1050,1029,1021,970,938,918,903,855,845,762,682,633,601,588,528；
Elemental analysis for C52H48N4Cl4O4Pd2,found C 53.90％,H：4.353％；N:4.68％；requires C 54.42％,H 4.22％,N 4.88％；
ESI(C52H48N4Cl4O4Pd2·H2O)m+1/e:Calcd:1166.6430；found:1166.5046其晶体数据如下
经验式 C52H48N4Cl4O4Pd2
分子量 1147.54
温度 293(2)K
波长
晶系，空间群 三斜晶系,P21
晶胞参数 α＝90°.
β＝90°.
γ＝90°.
体积
电荷密度 4,1.529 Mg/m^3
吸收校正参数 8.182 mm^-1
单胞内的电子数目 968.0
晶体大小 0.20x0.18x0.15mm
Theta角的范围 7.938 to 145.852
HKL的指标收集范围 -45<＝h<＝41,-9<k<14，-14<l<＝13
收集/独立衍射数据 20868/9073[R(int)＝0.0463]
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 9073/0/595
精修使用的方法 1.086
衍射点的一致性因子 R1＝0.0504，ωR2＝0.1090
可观察衍射的吻合因子 R1＝0.0615,ωR2＝0.1150
差值傅里叶图上的最大峰顶和峰谷
表1晶体的键长数据
表2晶体的键角数据
二苯甲酮腙与三甲基硅腈的反应应用
称取0.01147g钯配合物I，二苯甲酮肟0.0197g,三甲基硅腈0.2mL放入25mL烧瓶中，加入2.0mL二氯甲烷溶液中室温搅拌使其溶解；反应48小时后，加入水，用二氯甲烷(3x15)mL萃取，进行柱层析分离,将第一组分点自然挥发，得目标化合物晶体I；转化率：74％；1HNMR(600MHz,CDCl3,27),℃δ(ppm)＝7.66(d,J＝7.5Hz,3H),7.52-7.58(m,3H),7.43-7.48(m,11H),7.35(d,J＝7.4Hz，3H)，7.28-7.30(m,5H),7.19-7.22(m,5H)。

Claims (3)

1.一种手性钯配合物，其化学式如下：
2.权利要求1所述手性配合物的合成方法，包括反应、分离和纯化，其特征是由1，4-二氰基苯39.2mmol和D-苯丙氨醇16.2075g在无水无氧条件下和催化剂无水ZnCl2于氯苯溶剂中回流反应60小时，然后分离、纯化，反应结束后脱去氯苯，将粗产品用石油醚:二氯甲烷＝4:1进行柱层析分离,得白色噁唑啉晶体,再按照噁唑啉与氯化钯按质量比为1.42：1.70，以氯苯为溶剂反应，用二氯甲烷及乙醇进行重结晶，得红褐色双核氯化钯配合物单晶。
3.权利要求1所述手性配合物的用途，其特征在于：作为催化剂在二苯甲酮肟与三甲基硅腈的反应中显示了较好的催化效果，其转化率达74％。
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