(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(methoxy-diphenyl-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 866011-42-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(methoxy-diphenyl-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[methoxy(diphenyl)methyl]pyrrolidine-1-carboxylate
• CAS: 866011-42-9
• 化学式: C₂₉H₄₃NO₄Si
• 分子量: 497.75
• InChiKey: AUZNDNTXRFINAR-RPBOFIJWSA-N

物化性质

• 沸点：
  523.6±50.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(methoxy-diphenyl-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 水 为溶剂， 生成 (3R,5S)-5-(methoxydiphenylmethyl)pyrrolidin-3-ol
  参考文献：
  名称：

  CHIRAL SYNTHESIS OF NORNICOTINE AND NICOTINE

  摘要：

  The present invention relates to a method of producing nornicotine through enantioselective hydrosilylation of myosmine and a composition produced thereby, as well as a composition comprising nornicotine and a catalyst, wherein the catalyst is an organic chiral Lewis base, and a catalyst. The present invention also relates to a method of producing nicotine or a salt thereof from myosmine through enantioselective hydrosilylation of myosmine to nornicotine and further reacting the nornicotine to nicotine or a salt thereof, and a composition produced thereby, as well as a composition comprising nicotine, or a salt thereof, and a catalyst, wherein the catalyst is an organic chiral Lewis base.

  公开号：

  WO2024047152A1
• 作为产物：
  描述：

  N-Boc-反式-4-羟基-L-脯氨酸甲酯 在 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(methoxy-diphenyl-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  CHIRAL SYNTHESIS OF NORNICOTINE AND NICOTINE

  摘要：

  The present invention relates to a method of producing nornicotine through enantioselective hydrosilylation of myosmine and a composition produced thereby, as well as a composition comprising nornicotine and a catalyst, wherein the catalyst is an organic chiral Lewis base, and a catalyst. The present invention also relates to a method of producing nicotine or a salt thereof from myosmine through enantioselective hydrosilylation of myosmine to nornicotine and further reacting the nornicotine to nicotine or a salt thereof, and a composition produced thereby, as well as a composition comprising nicotine, or a salt thereof, and a catalyst, wherein the catalyst is an organic chiral Lewis base.

  公开号：

  WO2024047152A1

文献信息

• Immobilization of Oligostyrene-Prolinol Conjugates into Polystyrene via Electrospinning and Applications of these Fibers in Catalysis
  作者：Joachim Wendorff、Armido Studer、Caren Röben、Michael Stasiak、Birgit Janza、Andreas Greiner

  DOI：10.1055/s-2008-1067146

  日期：2008.7

  This paper reports the synthesis of prolinol-oligostytrene conjugates and their immobilization into a polystyrene matrix by using the electrospinning process. Via this approach fibers with a large surface area (fiber diameter of 1.2 µm) containing the prolinol conjugate are readily obtained. The fibers are shown to be catalytically active in a test Michael reaction. The fibrous catalyst system can readily be removed from the reaction mixture and be reused. However, a decrease of the catalyst activity was noticed upon recycling the fibrous catalyst systems.

  本文报道了以电纺法合成的脯氨醇-低聚苯乙烯共轭物，并将其固定于聚苯乙烯基质中的研究。通过这种方法可以轻松地获得具有较大表面积（纤维直径为1.2微米）且含有脯氨醇共轭物的纤维。这些纤维在迈克尔反应测试中表现出催化活性。该纤维催化剂系统可以轻松地从反应混合物中去除并重复使用。然而，在循环使用纤维催化剂系统时注意到催化活性的下降。
• Diphenylprolinol Methyl Ether:  A Highly Enantioselective Catalyst for Michael Addition of Aldehydes to Simple Enones
  作者：Yonggui Chi、Samuel H. Gellman

  DOI：10.1021/ol0517729

  日期：2005.9.1

  [reaction: see text] Diphenylprolinol methyl ether catalyzes intermolecular Michael addition of simple aldehydes to relatively nonactivated enones with the highest enantioselectivities reported to date (95-99% ee) and significantly lower catalyst loadings than have been typical in this arena.

  [反应：见正文]二苯基脯氨醇甲醚催化简单的分子间迈克尔加成到相对未活化的烯酮上，迄今为止报道的对映选择性最高（95-99％ee），并且催化剂的负载量大大低于该领域的典型水平。