tert-butyl (2S,4S)-4-cyano-2-methylpyrrolidine-1-carboxylate | 1004750-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,4S)-4-cyano-2-methylpyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S,4S)-4-cyano-2-methyl-pyrrolidine-1-carboxylate
• CAS: 1004750-57-5
• 化学式: C₁₁H₁₈N₂O₂
• 分子量: 210.276
• InChiKey: PVSSRFOUDVSLLJ-DTWKUNHWSA-N

物化性质

• 沸点：
  315.5±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4S)-4-cyano-2-methylpyrrolidine-1-carboxylate 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (3S,5S)-1-(tert-butoxycarbonyl)-5-methylpyrrolidine-3-carboxylic acid hydrochloride
  参考文献：
  名称：

  [EN] AMIDE DERIVATIVES USEFUL IN THE TREATMENT OF HBV INFECTION OR HBV-INDUCED DISEASES
  [FR] DÉRIVÉS D'AMIDE UTILES DANS LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B OU DE MALADIES INDUITES PAR LE VIRUS DE L'HÉPATITE B

  摘要：

  该申请涉及酰胺衍生物，其制备方法，药物组合物以及它们的用途，更具体地说，它们在治疗慢性乙型肝炎病毒（HBV）感染中的用途。

  公开号：

  WO2020225230A1
• 作为产物：
  描述：

  (2S,4R)-1BOC-4-methanesulfonyloxy-2-methylpyrrolidine 在 氰化钠 作用下， 以 二甲基亚砜 为溶剂， 生成 tert-butyl (2S,4S)-4-cyano-2-methylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Catalysis of 3-Pyrrolidinecarboxylic Acid and Related Pyrrolidine Derivatives in Enantioselective anti-Mannich-Type Reactions:  Importance of the 3-Acid Group on Pyrrolidine for Stereocontrol

  摘要：

  The development of enantioselective anti-selective Mannich-type reactions of aldehydes and ketones with imines catalyzed by 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives is reported in detail. Both (3R,5R)-5-methyl-3-pyrrolidinecarboxylic acid and (R)-3-pyrrolidinecarboxylic acid efficiently catalyzed the reactions of aldehydes with alpha-imino esters under mild conditions and afforded anti-Mannich products with high diastereo- and enantioselectivities (anti/syn up to 99:1, up to >99% ee). For the reactions of ketones with a-imino esters, (R)-3-pyrrolidinecarboxylic acid was an efficient catalyst (anti/syn up to >99:1, up to 99% ee). Evaluation of a series of pyrrolidine-based catalysts indicated that the acid group at the beta-position of the pyrrolidine ring of the catalyst played an important role in forwarding the carbon-carbon bond formation and in directing anti-selectivity and enantioselectivity.

  DOI：

  10.1021/ja074907+

文献信息

• AMIDE DERIVATIVES USEFUL IN THE TREATMENT OF HBV INFECTION OR HBV-INDUCED DISEASES
  申请人：Janssen Sciences Ireland Unlimited Company

  公开号：US20200352925A1

  公开（公告）日：2020-11-12

  The application relates to amide derivatives, processes for their preparation, pharmaceutical compositions, and their uses, more particularly their uses in treating chronic hepatitis B virus (HBV) infection.