3,4-(3S,4R)-dichloropyrrolidine-1,2-(2S)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester | 204398-86-7

• 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: 3,4-(3S,4R)-dichloropyrrolidine-1,2-(2S)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
• 英文别名: O1-tert-butyl O2-methyl (2R,3S,4R)-3,4-dichloropyrrolidine-1,2-dicarboxylate；1-O-tert-butyl 2-O-methyl (2R,3S,4R)-3,4-dichloropyrrolidine-1,2-dicarboxylate
• CAS: 204398-86-7
• 化学式: C₁₁H₁₇Cl₂NO₄
• 分子量: 298.166
• InChiKey: MVBSYSGTHGYKFP-PRJMDXOYSA-N

物化性质

• 沸点：
  367.8±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  3,4-(3S,4R)-dichloropyrrolidine-1,2-(2S)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 在 盐酸 作用下， 反应 2.0h， 以99%的产率得到methyl (2R,3S,4R)-3,4-dichloropyrrolidin-1-ium-2-carboxylate;chloride
  参考文献：
  名称：

  Synthetic studies toward astins A, B and C. Efficient syntheses of cis-3,4-dihydroxyprolines and (−)-(3S,4R)-dichloroproline esters

  摘要：

  Efficient syntheses of the esters of cis-3,4-dihydroxyprolines and the first synthesis of the ester of the rare amino acid (-)-(3S,4R)-dichloroproline from trans-4-hydroxy-L-proline are presented. The synthetic route provides easy access to several substituted prolines and cis-hydroxylated proline esters. Various types of biological activities have been associated with these substituted prolines. The role of (-)-(3S,4R)-dichloroproline in astins A, B and C is under investigation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00617-4
• 作为产物：
  描述：

  2-methyl 1-(2-methyl-2-propanyl) (2S,3R,4S)-3,4-dihydroxy-1,2-pyrrolidinedicarboxylate 在 三苯基膦 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 以74.5%的产率得到3,4-(3S,4R)-dichloropyrrolidine-1,2-(2S)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
  参考文献：
  名称：

  Synthetic studies toward astins A, B and C. Efficient syntheses of cis-3,4-dihydroxyprolines and (−)-(3S,4R)-dichloroproline esters

  摘要：

  Efficient syntheses of the esters of cis-3,4-dihydroxyprolines and the first synthesis of the ester of the rare amino acid (-)-(3S,4R)-dichloroproline from trans-4-hydroxy-L-proline are presented. The synthetic route provides easy access to several substituted prolines and cis-hydroxylated proline esters. Various types of biological activities have been associated with these substituted prolines. The role of (-)-(3S,4R)-dichloroproline in astins A, B and C is under investigation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00617-4

文献信息

• Synthetic studies toward astins A, B and C. Efficient syntheses of cis-3,4-dihydroxyprolines and (−)-(3S,4R)-dichloroproline esters
  作者：Kelly K. Schumacher、Jianjun Jiang、Madeleine M. Joullié

  DOI：10.1016/s0957-4166(97)00617-4

  日期：1998.1

  Efficient syntheses of the esters of cis-3,4-dihydroxyprolines and the first synthesis of the ester of the rare amino acid (-)-(3S,4R)-dichloroproline from trans-4-hydroxy-L-proline are presented. The synthetic route provides easy access to several substituted prolines and cis-hydroxylated proline esters. Various types of biological activities have been associated with these substituted prolines. The role of (-)-(3S,4R)-dichloroproline in astins A, B and C is under investigation. (C) 1998 Elsevier Science Ltd. All rights reserved.