Hydroquinidine 4-chlorobenzoate | 113162-02-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: Hydroquinidine 4-chlorobenzoate
• 英文别名: [(S)-[(2R,4S,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl] 4-chlorobenzoate
• CAS: 113162-02-0
• 化学式: C₂₇H₂₉ClN₂O₃
• 分子量: 465.0
• InChiKey: TXVNNFDXQZFMBQ-XHYUFEOFSA-N

物化性质

• 熔点：
  102-105 °C(lit.)
• 沸点：
  598.0±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xi
• 安全说明：
  S22,S24/25,S26,S36
• 危险类别码：
  R36/37/38
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险品运输编号：
  UN 1544
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  反式-1,2-二苯乙烯 、 N-甲基吗啉氧化物 、 、 Hydroquinidine 4-chlorobenzoate 、 、 Sodium sulfate-III 、 、 在 四氧化锇 丙酮 、 乙酸乙酯 、 水 、 Sodium sulfate-III 、 diol 、 乙醇 作用下， 以 olefin 、 二氯甲烷 、 乙醚 、 水 为溶剂， 反应 42.0h， 以afforded 172-180 g (80-84%) of enantiomerically pure stilbene diol as a white solid, mp 145.5°-146.5° C., [α]D25 =91.1° (c=1.209, abs EtOH)的产率得到Stilbenediol
  参考文献：
  名称：

  Ligands for ADH: cinchona alkaloids and moderately sized organic

  摘要：

  讨论了铂族金属催化烯烃加成的方法。在本发明的不对称双羟基化方法中，将烯烃、手性配体、有机溶剂、水溶液、碱、铁氰化盐和含铂族金属化合物组合。手性配体是一种生物碱或生物碱衍生物，通过平面芳香间隔基团连接至分子量至少为300道尔顿的有机取代基。有机取代基可以是另一种生物碱或生物碱衍生物。使用所述手性配体，可以实现高产率和对映选择性的烯烃不对称双羟基化。

  公开号：

  US05260461A1

文献信息

• Facilitation of turnover in the ADH by additives which catalyze the
  申请人：Massachusetts Institute of Technology

  公开号：US05227543A1

  公开（公告）日：1993-07-13

  Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant, an osmium-containing compound and an organic soluble anion are combined. The presence of the organic soluble anion allows the asymmetric dihydroxylation reaction to occur rapidly and the amount of olefin that is diydroxylated is high with concomitantly less chiral ligand and osmium-containing catalyst than previously achieved.

  讨论了铱催化的烯烃加成方法。在本发明的不对称二羟基化方法中，将烯烃、手性配体、有机溶剂、水、氧化剂、含铱化合物和有机可溶性阴离子结合在一起。有机可溶性阴离子的存在使得不对称二羟基化反应迅速发生，并且二羟基化的烯烃量高，同时所需的手性配体和含铱催化剂的量比以前实现的更少。
• Ligands for ADH: cinchona alkaloids and moderately sized organic
  申请人：Massachusetts Institute of Technology

  公开号：US05260461A1

  公开（公告）日：1993-11-09

  Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, an aqueous solution, a base, a ferricyanide salt and an osmium-containing compound are combined. The chiral ligand is an alkaloid or alkaloid derivative linked to an organic substituent of at least 300 daltons molecular weight through a planar aromatic spacer group. The organic substituent can be another alkaloid or alkaloid derivative. With the described chiral ligands, asymmetric dihydroxylation of olefins with high yields and enantiomeric excesses are achieved.

  讨论了铂族金属催化烯烃加成的方法。在本发明的不对称双羟基化方法中，将烯烃、手性配体、有机溶剂、水溶液、碱、铁氰化盐和含铂族金属化合物组合。手性配体是一种生物碱或生物碱衍生物，通过平面芳香间隔基团连接至分子量至少为300道尔顿的有机取代基。有机取代基可以是另一种生物碱或生物碱衍生物。使用所述手性配体，可以实现高产率和对映选择性的烯烃不对称双羟基化。
• Methods for catalytic asymmetric dihydroxylation of olefins
  申请人：Massachusetts Institute of Technology

  公开号：US05126494A1

  公开（公告）日：1992-06-30

  Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallo-chloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.

  本文讨论了铂铱催化剂对烯烃加成的方法。在本发明的不对称二羟基化方法中，将烯烃、手性配体、有机溶剂、水、氧化剂和含铂铱化合物混合。在本发明的不对称氧胺化方法中，将烯烃、手性配体、有机溶剂、水、金属氯胺衍生物、含铂铱化合物和可选的四烷基铵化合物混合。在本发明的不对称二胺化方法中，将烯烃、手性配体、有机溶剂、金属氯胺衍生物、胺和含铂铱化合物混合。在一种实施方式中，将烯烃、聚二羟基喹啉衍生物或二羟基喹啉衍生物的手性配体、丙酮、水、碱、氧化剂和四氧化锇混合以实现烯烃的不对称二羟基化。
• Method for catalytic asymmetric dihydroxylation of olefins using
  申请人：Massachusetts Institute of Technology

  公开号：US05516929A1

  公开（公告）日：1996-05-14

  Osmium-catalyzed methods of addition to an olefin are discussed. In the method of asymmetric dihydroxylation of the present invention, an olefin, a chiral ligand, an organic solvent, water, an oxidant and an osmium-containing compound are combined. In the method of asymmetric oxyamination of the present invention, an olefin, a chiral ligand, an organic solvent, water, a metallochloramine derivative, an osmium-containing compound and, optionally, a tetraalkyl ammonium compound are combined. In the method of asymmetric diamination of the present invention, an olefin, a chiral ligand, an organic solvent, a metallo-chloramine derivative, an amine and an osmium-containing compound are combined. In one embodiment, an olefin, a chiral ligand which is a polymeric dihydroquinidine derivative or a dihydroquinine derivative, acetone, water, a base, an oxidant and osmium tetroxide are combined to effect asymmetric dihydroxylation of the olefin.

  本文讨论了奥兹米催化的烯烃加成方法。在本发明的不对称双羟基化方法中，将烯烃、手性配体、有机溶剂、水、氧化剂和含奥兹米的化合物混合。在本发明的不对称氧胺化方法中，将烯烃、手性配体、有机溶剂、水、金属氯胺衍生物、含奥兹米的化合物和可选的四烷基铵化合物混合。在本发明的不对称二胺化方法中，将烯烃、手性配体、有机溶剂、金属氯胺衍生物、胺和含奥兹米的化合物混合。在一种实施方式中，将烯烃、聚合二羟基喹啉衍生物或二喹啉衍生物的手性配体、丙酮、水、碱、氧化剂和四氧化二锇混合，以实现烯烃的不对称双羟基化。