(S)-N-(1,4-benzodioxan-2-carbonyl)piperazine D-tartrate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (S)-N-(1,4-benzodioxan-2-carbonyl)piperazine D-tartrate
• 英文别名: [(3S)-2,3-dihydro-1,4-benzodioxin-3-yl]-piperazin-4-ium-1-ylmethanone;(2S,3S)-2,3,4-trihydroxy-4-oxobutanoate
• 化学式: C₄H₆O₆*C₁₃H₁₆N₂O₃
• 分子量: 398.37
• InChiKey: XOXJZSXWIQYRCA-RBTVCSKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.23
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  173
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-N-(1,4-benzodioxan-2-carbonyl)piperazine D-tartrate 在 potassium carbonate 作用下， 生成 (S)-1,4-苯并二噁烷-2-羧基哌嗪
  参考文献：
  名称：

  Practical chemical and enzymatic technologies for (S)-1,4-benzodioxan-2-carboxypiperizine intermediate in the synthesis of (S)-doxazosin mesylate

  摘要：

  (S)-1,4-Benzodioxan-2-carboxypiperazine (S)-2, the key chiral intermediate for the synthesis of (S)-doxazosin, was prepared utilizing two approaches: (i) enzymatic resolution of ethyl 1,4-benzodioxan-2-carboxylate with an esterase (Serratia) followed by an-de formation; (ii) direct resolution of 1,4-benzodioxan-2-carboxypiperazine 2 with D-tartaric acid. An efficient process for the conversion of (S)-2 to (S)-doxazosin mesylate was developed (80% yield, 99.9% e.e.). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00368-8
• 作为产物：
  描述：

  D-酒石酸 、 N-(1,4-苯并二烷-2-羰基)哌嗪 以 水 、 乙腈 为溶剂， 以50%的产率得到(S)-N-(1,4-benzodioxan-2-carbonyl)piperazine D-tartrate
  参考文献：
  名称：

  Practical chemical and enzymatic technologies for (S)-1,4-benzodioxan-2-carboxypiperizine intermediate in the synthesis of (S)-doxazosin mesylate

  摘要：

  (S)-1,4-Benzodioxan-2-carboxypiperazine (S)-2, the key chiral intermediate for the synthesis of (S)-doxazosin, was prepared utilizing two approaches: (i) enzymatic resolution of ethyl 1,4-benzodioxan-2-carboxylate with an esterase (Serratia) followed by an-de formation; (ii) direct resolution of 1,4-benzodioxan-2-carboxypiperazine 2 with D-tartaric acid. An efficient process for the conversion of (S)-2 to (S)-doxazosin mesylate was developed (80% yield, 99.9% e.e.). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00368-8

文献信息

• Practical chemical and enzymatic technologies for (S)-1,4-benzodioxan-2-carboxypiperizine intermediate in the synthesis of (S)-doxazosin mesylate
  作者：Q.Kevin Fang、Paul Grover、Zhengxu Han、Fran X. McConville、Richard F. Rossi、Damase J. Olsson、Donald W. Kessler、Stephen A. Wald、Chris H. Senanayake

  DOI：10.1016/s0957-4166(01)00368-8

  日期：2001.8

  (S)-1,4-Benzodioxan-2-carboxypiperazine (S)-2, the key chiral intermediate for the synthesis of (S)-doxazosin, was prepared utilizing two approaches: (i) enzymatic resolution of ethyl 1,4-benzodioxan-2-carboxylate with an esterase (Serratia) followed by an-de formation; (ii) direct resolution of 1,4-benzodioxan-2-carboxypiperazine 2 with D-tartaric acid. An efficient process for the conversion of (S)-2 to (S)-doxazosin mesylate was developed (80% yield, 99.9% e.e.). (C) 2001 Elsevier Science Ltd. All rights reserved.