1-(4-Methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester | 205443-19-2

• 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: 1-(4-Methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester
• 英文别名: Methyl 1-[(4-methoxyphenyl)methyl]azetidine-2-carboxylate
• CAS: 205443-19-2
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: OXHKDWRXLFVADA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-Methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester 生成 (R)-(+)-methyl 1-(4-methoxybenzyl)azetidine-2-carboxylate
  参考文献：
  名称：

  Enzymatic resolution of methyl N-alkyl-azetidine-2-carboxylates by Candida antarctica lipase-mediated ammoniolysis

  摘要：

  A facile method for the synthesis of optically active azetidine-2-carboxylic acid derivatives is presented. Racemic N-alkylated azetidine esters are resolved by lipase from Candida antarctica in an ammoniolysis reaction, and both the S-amide and the R-ester are obtained with excellent stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00632-0
• 作为产物：
  描述：

  2,4-二溴丁酸甲酯 、 4-甲氧基苄胺 在 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 以39%的产率得到1-(4-Methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Enzymatic resolution of methyl N-alkyl-azetidine-2-carboxylates by Candida antarctica lipase-mediated ammoniolysis

  摘要：

  A facile method for the synthesis of optically active azetidine-2-carboxylic acid derivatives is presented. Racemic N-alkylated azetidine esters are resolved by lipase from Candida antarctica in an ammoniolysis reaction, and both the S-amide and the R-ester are obtained with excellent stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00632-0

文献信息

• Method for racemization of optically active azetidine-2-carboxylate
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP0957089A1

  公开（公告）日：1999-11-17

  A method for racemization of an optically active N-substituted azetidine-2-carboxylic acid ester of the formula (1): wherein * represents an asymmetric carbon atom, R1 represents an optionally substituted aryl group, a saturated hydrocarbon group which may be substituted with an optionally substituted aryl group, or an unsaturated hydrocarbon group, R2 represents a saturated hydrocarbon group which may be substituted, an optionally substituted unsaturated hydrocarbon group, an alkyloxycarbonyl group which may be substituted, an alkenyloxycarbonyl group, or an optionally substituted sulfonyl group,    which comprises heating the ester of the formula (1) at 100°C or higher or subjecting the ester to contact with a basic compound selected from an alkali metal hydride, an alkali metal alkoxide of a tertiary alcohol and an organic amine.

  一种式（1）的具有光学活性的 N-取代氮杂环丁烷-2-羧酸酯的消旋化方法： 其中 * 代表不对称碳原子、 R1 代表任选取代的芳基、可被任选取代的芳基取代的饱和烃基或不饱和烃基、 R2 代表可被取代的饱和烃基、可被取代的不饱和烃基、可被取代的烷氧羰基、烯氧羰基或可被取代的磺酰基、 其中包括在 100°C 或更高温度下加热式（1）的酯，或使酯与选自碱金属氢化物、叔醇的碱金属烷氧化物和有机胺的碱性化合物接触。
• Method for racemization of optically active azetidine-2-Carboxylate
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1201653B1

  公开（公告）日：2005-04-20
• US6166224A
  申请人：——

  公开号：US6166224A

  公开（公告）日：2000-12-26