tert-butyl (2RS,E)-3-(2'-bromoethylidene)-1-tert-butoxycarbonyl-azetidine-2-carboxylate | 144572-36-1

• 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: tert-butyl (2RS,E)-3-(2'-bromoethylidene)-1-tert-butoxycarbonyl-azetidine-2-carboxylate
• 英文别名: ditert-butyl (3E)-3-(2-bromoethylidene)azetidine-1,2-dicarboxylate
• CAS: 144572-36-1
• 化学式: C₁₅H₂₄BrNO₄
• 分子量: 362.264
• InChiKey: JVMSWEZBQYWDKL-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2RS,E)-3-(2'-bromoethylidene)-1-tert-butoxycarbonyl-azetidine-2-carboxylate 在 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以81%的产率得到tert-butyl (2RS,E)-1-tert-butoxycarbonyl-3-ethylidene-azetidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of (2RS,E)-3-Ethylidene-azetidine-2-carboxylic acid (rac. polyoximic acid)

  摘要：

  Treatment of alpha-diazo beta-ketoester 4 with a catalytic amount of rhodium (II) acetate followed by Wittig reaction with phosphorane 5 gave the isomeric phenylthioester derivative 6a and 6b. Reduction of 6a led to the corresponding allylic alcohol 7, which was further converted into the bromide 8. Dehalogenation of 8 with NaBH4/DMF resulted in compound 9, which was deprotected with trifluoroacetic acid, giving racemic polyoximic acid (1).

  DOI：

  10.1016/s0040-4020(01)88257-0
• 作为产物：
  描述：

  tert-butyl (2RS,E)-1-tert-butoxycarbonyl-3-(phenylthiocarbonyl-methylidene)-azetidine-2-carboxylate 在 sodium tetrahydroborate 、 cerium(III) chloride 、 四溴化碳 、 1,2-双(二苯基膦)乙烷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 tert-butyl (2RS,E)-3-(2'-bromoethylidene)-1-tert-butoxycarbonyl-azetidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of (2RS,E)-3-Ethylidene-azetidine-2-carboxylic acid (rac. polyoximic acid)

  摘要：

  Treatment of alpha-diazo beta-ketoester 4 with a catalytic amount of rhodium (II) acetate followed by Wittig reaction with phosphorane 5 gave the isomeric phenylthioester derivative 6a and 6b. Reduction of 6a led to the corresponding allylic alcohol 7, which was further converted into the bromide 8. Dehalogenation of 8 with NaBH4/DMF resulted in compound 9, which was deprotected with trifluoroacetic acid, giving racemic polyoximic acid (1).

  DOI：

  10.1016/s0040-4020(01)88257-0

文献信息

• Synthesis of (2RS,E)-3-Ethylidene-azetidine-2-carboxylic acid (rac. polyoximic acid)
  作者：Gerhard Emmer

  DOI：10.1016/s0040-4020(01)88257-0

  日期：1992.1

  Treatment of alpha-diazo beta-ketoester 4 with a catalytic amount of rhodium (II) acetate followed by Wittig reaction with phosphorane 5 gave the isomeric phenylthioester derivative 6a and 6b. Reduction of 6a led to the corresponding allylic alcohol 7, which was further converted into the bromide 8. Dehalogenation of 8 with NaBH4/DMF resulted in compound 9, which was deprotected with trifluoroacetic acid, giving racemic polyoximic acid (1).