tert-butyl (2S)-2-methyl-5-oxopyrrolidine-2-carboxylate | 882392-64-5

• 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 (2S)-2-methyl-5-oxopyrrolidine-2-carboxylate
• CAS: 882392-64-5
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: VHMVPTHFTIAYBB-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-methyl-5-oxopyrrolidine-2-carboxylate 在 盐酸 、 4-二甲氨基吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 10.5h， 生成 (S)-2-甲基脯氨酸
  参考文献：
  名称：

  Catalytic Asymmetric Michael Reaction under Phase-Transfer Catalysis: Construction of Chiral Tetrasubstituted Carbon and Its Application to the Synthesis of a Chiral Pyrrolidone

  摘要：

  A catalytic asymmetric Michael reaction using Schiff bases promoted by D-2-symmetrical ammonium salts as phase-transfer catalysts is described. The reaction of glycine Schiff base (1a) gave the Michael adduct with up to 91% ee and tetrasubstituted carbons was also constructed using alanine Schiff base (3a) with up to 63% ee.

  DOI：

  10.3987/com-05-s(t)41
• 作为产物：
  描述：

  在 柠檬酸 作用下， 以 四氢呋喃 为溶剂， 反应 45.0h， 生成 tert-butyl (2S)-2-methyl-5-oxopyrrolidine-2-carboxylate
  参考文献：
  名称：

  Catalytic Asymmetric Michael Reaction under Phase-Transfer Catalysis: Construction of Chiral Tetrasubstituted Carbon and Its Application to the Synthesis of a Chiral Pyrrolidone

  摘要：

  A catalytic asymmetric Michael reaction using Schiff bases promoted by D-2-symmetrical ammonium salts as phase-transfer catalysts is described. The reaction of glycine Schiff base (1a) gave the Michael adduct with up to 91% ee and tetrasubstituted carbons was also constructed using alanine Schiff base (3a) with up to 63% ee.

  DOI：

  10.3987/com-05-s(t)41

文献信息

• CYP3A4 catalyzes the rearrangement of the dual orexin receptor antagonist daridorexant to 4‐hydroxy piperidinol metabolites
  作者：Alexander Treiber、Hamed Aissaoui、Stéphane Delahaye、Sven Glutz、Julien Grimont、Claus Müller、Swen Seeland、Valérie Siefken、Christoph Boss

  DOI：10.1002/cmdc.202300030

  日期：——

  monooxygenase CYP3A4 catalyzes the intramolecular rearrangement of the dual orexin receptor antagonist daridorexant. Hydroxylation in 5-position of the pyrrolidine ring initially yields a cyclic hemiaminal which subsequently hydrolyzes to a ring-open amino aldehyde. Cyclization of the latter onto one of the nitrogen atoms of the benzimidazole moiety yields the final 4-hydroxy piperidinol metabolite.

  人单加氧酶CYP3A4 催化双重食欲素受体拮抗剂 daridorexant 的分子内重排。吡咯烷环 5 位的羟基化最初产生环状半缩醛胺，随后水解为开环氨基醛。后者在苯并咪唑部分的一个氮原子上环化产生最终的 4-羟基哌啶醇代谢物。
• Catalytic Asymmetric Michael Reaction under Phase-Transfer Catalysis: Construction of Chiral Tetrasubstituted Carbon and Its Application to the Synthesis of a Chiral Pyrrolidone
  作者：Shigeru Arai、Fumie Takahashi、Riichiro Tsuji、Atsushi Nishida

  DOI：10.3987/com-05-s(t)41

  日期：——

  A catalytic asymmetric Michael reaction using Schiff bases promoted by D-2-symmetrical ammonium salts as phase-transfer catalysts is described. The reaction of glycine Schiff base (1a) gave the Michael adduct with up to 91% ee and tetrasubstituted carbons was also constructed using alanine Schiff base (3a) with up to 63% ee.