dimethyl (2R,3R)-(+)-1-methylsulfonylaziridine-2,3-dicarboxylate | 155976-03-7

• 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: dimethyl (2R,3R)-(+)-1-methylsulfonylaziridine-2,3-dicarboxylate
• 英文别名: dimethyl (2R,3R)-1-methylsulfonylaziridine-2,3-dicarboxylate
• CAS: 155976-03-7
• 化学式: C₇H₁₁NO₆S
• 分子量: 237.233
• InChiKey: YSTWFIHTTRUUMI-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  98.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl (2R,3R)-(+)-1-methylsulfonylaziridine-2,3-dicarboxylate 在 sodium azide 、 四丁基硫酸氢铵 作用下， 以 氯仿 、 水 为溶剂， 反应 16.0h， 以60%的产率得到(2R,3S)-2-Azido-3-methanesulfonylamino-succinic acid dimethyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Erythro β-Substituted Aspartates

  摘要：

  The nucleophilic ring opening of trans-aziridine-2,3-dicarboxylate 1 and substituted N-acyl-, N-(methoxycarbonyl)-, and N-(methanesulfonyl)aziridine-2,3-dicarboxylates 2-4 allows an easy synthetic approach to beta-hydroxy, beta-amino, beta-(alkylthio), and beta-halogenoaspartates 5-8; in this respect, compounds 2-4 display higher reactivities. The erythro stereochemistry of the synthesized aspartates and the S(N)2-like mechanism of the nucleophilic attack were unambiguously identified by the (2R,3S) X-ray absolute configuration determination of enantiomerically pure beta-amino derivative 9, obtained from (2R,3R)-4, and by its chemical correlation with meso alpha,beta-bis[N-(methanesulfonyl)amino]succinate (10).

  DOI：

  10.1021/jo971285+
• 作为产物：
  描述：

  dimethyl 1-methylsulfonylaziridine-2,3-dicarboxylate 在 sodium chloride 作用下， 以 水 为溶剂， 反应 24.0h， 生成 (2S,3S)-1-Methanesulfonyl-aziridine-2,3-dicarboxylic acid monomethyl ester 、 dimethyl (2R,3R)-(+)-1-methylsulfonylaziridine-2,3-dicarboxylate
  参考文献：
  名称：

  Bucciarelli, Maria; Forni, Arrigo; Moretti, Irene, Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 3041 - 3046

  摘要：

  DOI：

文献信息

• Bucciarelli, Maria; Forni, Arrigo; Moretti, Irene, Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 3041 - 3046
  作者：Bucciarelli, Maria、Forni, Arrigo、Moretti, Irene、Prati, Fabio、Torre, Giovanni

  DOI：——

  日期：——
• Stereoselective Synthesis of <i>Erythro</i> β-Substituted Aspartates
  作者：Luciano Antolini、Maria Bucciarelli、Emilia Caselli、Paolo Davoli、Arrigo Forni、Irene Moretti、Fabio Prati、Giovanni Torre

  DOI：10.1021/jo971285+

  日期：1997.12.1

  The nucleophilic ring opening of trans-aziridine-2,3-dicarboxylate 1 and substituted N-acyl-, N-(methoxycarbonyl)-, and N-(methanesulfonyl)aziridine-2,3-dicarboxylates 2-4 allows an easy synthetic approach to beta-hydroxy, beta-amino, beta-(alkylthio), and beta-halogenoaspartates 5-8; in this respect, compounds 2-4 display higher reactivities. The erythro stereochemistry of the synthesized aspartates and the S(N)2-like mechanism of the nucleophilic attack were unambiguously identified by the (2R,3S) X-ray absolute configuration determination of enantiomerically pure beta-amino derivative 9, obtained from (2R,3R)-4, and by its chemical correlation with meso alpha,beta-bis[N-(methanesulfonyl)amino]succinate (10).