(R)-3-Benzylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid tert-butyl ester | 329956-35-6

• 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: (R)-3-Benzylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid tert-butyl ester
• 英文别名: tert-butyl (3R)-3-(benzylamino)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate
• CAS: 329956-35-6
• 化学式: C₁₉H₂₉NO₄
• 分子量: 335.444
• InChiKey: VFYNQCSTPYTEDM-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-Benzylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid tert-butyl ester 在 potassium tert-butylate 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 (2R,3S)-1-Benzyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-oxo-pyrrolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of chiral pyrrolidine and pyrrole derivatives through the chemoselective Dieckmann reaction of α,β-aminodiesters

  摘要：

  alpha,beta -Aminodiesters were allowed to react with t-BuOK in THF at -78 degreesC. The chemoselectivity of the Dieckmann cyclization was controlled by the nature of the substituents R-3 and R-4, allowing the preparation of pyrrolidine or pyrrole derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00377-3
• 作为产物：
  描述：

  tert-butyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate 、 苄胺 反应 48.0h， 以67%的产率得到(R)-3-Benzylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propionic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of chiral pyrrolidine and pyrrole derivatives through the chemoselective Dieckmann reaction of α,β-aminodiesters

  摘要：

  alpha,beta -Aminodiesters were allowed to react with t-BuOK in THF at -78 degreesC. The chemoselectivity of the Dieckmann cyclization was controlled by the nature of the substituents R-3 and R-4, allowing the preparation of pyrrolidine or pyrrole derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00377-3

文献信息

• Synthesis of chiral pyrrolidine and pyrrole derivatives through the chemoselective Dieckmann reaction of α,β-aminodiesters
  作者：Américo C. Pinto、Rodrigo V. Abdala、Paulo R.R. Costa

  DOI：10.1016/s0957-4166(00)00377-3

  日期：2000.11

  alpha,beta -Aminodiesters were allowed to react with t-BuOK in THF at -78 degreesC. The chemoselectivity of the Dieckmann cyclization was controlled by the nature of the substituents R-3 and R-4, allowing the preparation of pyrrolidine or pyrrole derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.