3-(羧苯甲酰氨基)戊内酯 | 84787-51-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(羧苯甲酰氨基)戊内酯
• 英文名称: 3-(Carbobenzoxyamino)valerolactone
• 英文别名: benzyl N-[(4R)-2-oxooxan-4-yl]carbamate
• CAS: 84787-51-9
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: WGNIWBQMXGJLSC-LLVKDONJSA-N

物化性质

• 沸点：
  474.1±44.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(羧苯甲酰氨基)戊内酯 生成 benzyl N-[(3R,4R)-3-(2-hydroxypropan-2-yl)-2-oxooxan-4-yl]carbamate
  参考文献：
  名称：

  UMEHDZAVA, XAMAO;ONO, MASADZI

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-tert-Butyl 3-Amino-5-(tert-Butyldimethylsiloxy)pentanoate 在 三氟乙酸 作用下， 反应 1.5h， 生成 3-(羧苯甲酰氨基)戊内酯
  参考文献：
  名称：

  An asymmetric ammonia synthon for Michael additions

  摘要：

  The highly diastereoselective 1,4-addition of lithiated chiral amine 1 to alpha,beta-unsaturated esters, followed by hydrogenolysis of the benzylic-type C-N bonds of the 1,4-adducts, provides an asymmetric ammonia synthon for Michael additions. Under optimized conditions, lithiated 1 adds to alpha,beta-unsaturated tert-butyl esters in dimethoxyethane at -63-degrees-C in high yield with very high diastereoselectivity. Small, large, functionalized, and chiral beta-ester substituents are amenable, with (S)-1 consistently adding to (E)-3 from the top as drawn in Table II. Hydrogenolysis liberates the beta-amino esters with typically 95-99% ee.

  DOI：

  10.1021/jo00033a037

文献信息

• New synthesis of β-amino acids by nucleophilic addition of enolate anions to N-methoxycarbonylimines generated from α-methoxy carbamates1
  作者：Tatsuya Shono*、Naoki Kise、Fumio Sanda、Satoru Ohi、Kenji Tsubata

  DOI：10.1016/s0040-4039(00)80062-3

  日期：1988.1
• UMEHDZAVA, XAMAO;ONO, MASADZI
  作者：UMEHDZAVA, XAMAO、ONO, MASADZI

  DOI：——

  日期：——
• JPS5959652A
  申请人：——

  公开号：JPS5959652A

  公开（公告）日：1984-04-05
• An asymmetric ammonia synthon for Michael additions
  作者：Joel M. Hawkins、Timothy A. Lewis

  DOI：10.1021/jo00033a037

  日期：1992.3

  The highly diastereoselective 1,4-addition of lithiated chiral amine 1 to alpha,beta-unsaturated esters, followed by hydrogenolysis of the benzylic-type C-N bonds of the 1,4-adducts, provides an asymmetric ammonia synthon for Michael additions. Under optimized conditions, lithiated 1 adds to alpha,beta-unsaturated tert-butyl esters in dimethoxyethane at -63-degrees-C in high yield with very high diastereoselectivity. Small, large, functionalized, and chiral beta-ester substituents are amenable, with (S)-1 consistently adding to (E)-3 from the top as drawn in Table II. Hydrogenolysis liberates the beta-amino esters with typically 95-99% ee.