(S)-tert-butyl ((2-(butylamino)-4-oxo-4,5-dihydrofuran-3-yl)(phenyl)methyl)carbamate | 1346253-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (S)-tert-butyl ((2-(butylamino)-4-oxo-4,5-dihydrofuran-3-yl)(phenyl)methyl)carbamate
• 英文别名: tert-butyl N-[(S)-[2-(butylamino)-4-oxofuran-3-yl]-phenylmethyl]carbamate
• CAS: 1346253-43-7
• 化学式: C₂₀H₂₈N₂O₄
• 分子量: 360.453
• InChiKey: ZVNFUWQLTSAWMO-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 三乙胺 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 16.0h， 生成 (S)-tert-butyl ((2-(butylamino)-4-oxo-4,5-dihydrofuran-3-yl)(phenyl)methyl)carbamate
  参考文献：
  名称：

  Asymmetric synthesis of O-alkylated tetronic acid derivatives via an organocatalytic Mannich reaction and subsequent intramolecular cyclization

  摘要：

  The organocatalytic asymmetric Mannich reaction of ethyl 4-chloro-3-oxobutanoate with N-Boc-imines has been studied and Cinchona alkaloids and chiral thiourea-tertiary amines were evaluated as catalysts. A pyrrolidine-based thiourea-tertiary amine was identified as the best catalyst for the transformation. The Mannich adducts readily underwent a one-pot intramolecular cyclization in the presence of triethylamine. A number of O-ethyl tetronic acid derivatives were obtained in good yields and enantioselectivities (up to 91% ee). The products could be further converted to the heteroatomic mimics of prostaglandins via reaction with primary amines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.08.022

文献信息

• Asymmetric synthesis of O-alkylated tetronic acid derivatives via an organocatalytic Mannich reaction and subsequent intramolecular cyclization
  作者：Nian-hua Luo、Xiang Sun、Yun-yun Yan、Shao-zhen Nie、Ming Yan

  DOI：10.1016/j.tetasy.2011.08.022

  日期：2011.7

  The organocatalytic asymmetric Mannich reaction of ethyl 4-chloro-3-oxobutanoate with N-Boc-imines has been studied and Cinchona alkaloids and chiral thiourea-tertiary amines were evaluated as catalysts. A pyrrolidine-based thiourea-tertiary amine was identified as the best catalyst for the transformation. The Mannich adducts readily underwent a one-pot intramolecular cyclization in the presence of triethylamine. A number of O-ethyl tetronic acid derivatives were obtained in good yields and enantioselectivities (up to 91% ee). The products could be further converted to the heteroatomic mimics of prostaglandins via reaction with primary amines. (C) 2011 Elsevier Ltd. All rights reserved.