(R)-1-benzyl-4-methylazetidine-2-carboxylic acid

• 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)-1-benzyl-4-methylazetidine-2-carboxylic acid
• 英文别名: (2R,4S)-1-benzyl-4-methylazetidine-2-carboxylic acid
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: DPHJCCRLGZHNPB-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-benzyl-4-methylazetidine-2-carboxylic acid 、 草酰氯 以26%的产率得到
  参考文献：
  名称：

  WASSERMAN, H. H.;HAN, W. T.;SCHAUS, J. M.;FALLER, J. W., TETRAHEDRON LETT., 1984, 25, N 29, 3111-3114

  摘要：

  DOI：
• 作为产物：
  描述：

  (2RS,4SR)-1-benzyl-4-methylazetidine-2-carboxamide 在 Rhodococcus erythropolis AJ₂₇₀ 作用下， 反应 70.0h， 以47%的产率得到(2S,4R)-(-)-1-benzyl-4-methylazetidine-2-carboxamide
  参考文献：
  名称：

  Highly Efficient and Enantioselective Biotransformations of Racemic Azetidine-2-carbonitriles and Their Synthetic Applications

  摘要：

  Catalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst in neutral aqueous buffer at 30 degrees C, a number of racemic 1-benzylazetidine-2-carbonitriles, trans-1-benzyl-4-methylazetidine-2-carbonitrile. and 1-benzyl-2-methylazetidine-2-carbonitrile and their amide substrates underwent efficient and enantioselective biotransformations to afford the corresponding azetidine-2-carboxylic acids and their amide derivatives in excellent yields with cc up to >99.5%. The overall excellent, act enantioselectivity of the biocatalytic reactions stemmed from a combined effect of a very active but virtually nonenantioselective nitrite hydratase and a high R-enantioselective amidase involved in microbial whole cells. The synthetic applications have been demonstrated by the nucleophilic ring-opening reactions of azetidiniums of the resulting chiral azetidine-2-carbox amide derivatives for the preparation of alpha,gamma-diamino, alpha-phenoxy-gamma-amino, and alpha-cyano-gamma-amino carboxamides. The intramolecular Cul-catalyzed cross-coupling reaction for the synthesis of azetidine-fused 1,4-benzodiazepin-2-one derivative was also presented.

  DOI：

  10.1021/jo9011656

文献信息

• Stereochemical effects in the reactions of n-alkyl-4-substituted azetidine 2-carboxylic acids with oxalyl chloride. Rearrangement to chloro-γ-lactams.
  作者：Harry H. Wasserman、William T. Han、John M. Schaus、John W. Faller

  DOI：10.1016/0040-4039(84)80021-0

  日期：——

  Treatment of N-alkylazetidine 2-carboxylates with oxalyl chloride may yield acid chlorides, iminium salts or chloro-γ-lactams depending on the stereochemistry and nature of the substituents on the azetidine ring.

  用草酰氯处理N-烷基氮杂环丁烷2-羧酸盐可产生酰氯，亚胺盐或氯代-γ-内酰胺，这取决于氮杂环丁烷环上取代基的立体化学和性质。
• Soriano, David S.; Podraza, Kenneth F.; Cromwell, Norman H., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 623 - 624
  作者：Soriano, David S.、Podraza, Kenneth F.、Cromwell, Norman H.

  DOI：——

  日期：——