tert-butyl (3R)-3',3'-dicyano-1-methyl-5'-methylidene-2-oxospiro[indole-3,2'-pyrrolidine]-1'-carboxylate | 1429615-31-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (3R)-3',3'-dicyano-1-methyl-5'-methylidene-2-oxospiro[indole-3,2'-pyrrolidine]-1'-carboxylate
• CAS: 1429615-31-5
• 化学式: C₂₀H₂₀N₄O₃
• 分子量: 364.404
• InChiKey: HPUKONBQKYUHOE-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3R)-3',3'-dicyano-1-methyl-5'-methylidene-2-oxospiro[indole-3,2'-pyrrolidine]-1'-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以75%的产率得到(R)-1,5'-dimethyl-2-oxospiro[indoline-3,2'-pyrrole]-3',3'(4'H)-dicarbonitrile
  参考文献：
  名称：

  Asymmetric One-Pot Sequential Mannich/Hydroamination Reaction by Organo- and Gold Catalysts: Synthesis of Spiro[pyrrolidin-3,2′-oxindole] Derivatives

  摘要：

  An asymmetric organo- and gold-catalyzed one-pot sequential Mannich/hydroamination reaction has been developed. Using this protocol, spiro[pyrrolidin-3,2'-oxindole] derivatives were synthesized in good yields (up to 91%) and excellent enantioselectivities (up to 97% ee).

  DOI：

  10.1021/ol4004542
• 作为产物：
  描述：

  tert-butyl 1-methyl-2-oxoindolin-3-ylidenecarbamate 在 三氟化硼乙醚 、 9-O-(3,5-bis(trifluoromethyl)benzyl)-6'-hydroxycinchonidine 作用下， 以 甲苯 为溶剂， 反应 24.5h， 生成 tert-butyl (3R)-3',3'-dicyano-1-methyl-5'-methylidene-2-oxospiro[indole-3,2'-pyrrolidine]-1'-carboxylate
  参考文献：
  名称：

  Asymmetric One-Pot Sequential Mannich/Hydroamination Reaction by Organo- and Gold Catalysts: Synthesis of Spiro[pyrrolidin-3,2′-oxindole] Derivatives

  摘要：

  An asymmetric organo- and gold-catalyzed one-pot sequential Mannich/hydroamination reaction has been developed. Using this protocol, spiro[pyrrolidin-3,2'-oxindole] derivatives were synthesized in good yields (up to 91%) and excellent enantioselectivities (up to 97% ee).

  DOI：

  10.1021/ol4004542

文献信息

• Chiral Dinuclear Benzyliminobinaphthoxy‐Palladium Catalyst for Asymmetric Mannich Reaction of Aldimines and Isatin‐Derived Ketimines with Alkylmalononitriles
  作者：Ayu Nakamura、Satoru Kuwano、Junchuan Sun、Kensuke Araseki、Eri Ogino、Takayoshi Arai

  DOI：10.1002/adsc.202000447

  日期：2020.8.4

  A newly developed dinuclear bis(benzylimino)binaphthol (BIB )−Pd complex showed good catalytic activity for the Mannich reaction of aldimines and isatin‐derived ketimines with alkylmalononitriles to give the products in a highly enantioselective manner.

  一种新开发的双核双（苄基亚氨基）联萘酚（BIB）-Pd络合物对醛亚胺和源自靛红的酮亚胺与烷基丙二腈的曼尼希反应具有良好的催化活性，从而以高度对映选择性的方式提供了产物。
• Asymmetric One-Pot Sequential Mannich/Hydroamination Reaction by Organo- and Gold Catalysts: Synthesis of Spiro[pyrrolidin-3,2′-oxindole] Derivatives
  作者：Xianjie Chen、Hui Chen、Xun Ji、Hualiang Jiang、Zhu-Jun Yao、Hong Liu

  DOI：10.1021/ol4004542

  日期：2013.4.19

  An asymmetric organo- and gold-catalyzed one-pot sequential Mannich/hydroamination reaction has been developed. Using this protocol, spiro[pyrrolidin-3,2'-oxindole] derivatives were synthesized in good yields (up to 91%) and excellent enantioselectivities (up to 97% ee).