(S)-doxazosin hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (S)-doxazosin hydrochloride
• 英文别名: (+)-Doxazosin hydrochloride；[4-(4-amino-6,7-dimethoxyquinazolin-3-ium-2-yl)piperazin-1-yl]-[(3S)-2,3-dihydro-1,4-benzodioxin-3-yl]methanone;chloride
• 化学式: C₂₃H₂₅N₅O₅*ClH
• 分子量: 487.943
• InChiKey: AQAZIYFEPYHLHC-BDQAORGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-doxazosin hydrochloride 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到S-多沙唑嗪
  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：

  1,4-苯并二氧六环-2-甲酸乙酯 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 esterase from Serracia marcescens 、 碳酸氢钠 作用下， 以 甲醇 、 氘代氯仿 、 水 、 甲苯 、 正丁醇 为溶剂， 反应 29.5h， 生成 (S)-doxazosin hydrochloride
  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

• CAMPBELL S. F.; DAVEY M. J.; HARDSTONE J. D.; LEWIS B. N. (IN PART); PALM+, J. MED. CHEM., 30,(1987) N 1, 49-57
  作者：CAMPBELL S. F.、 DAVEY M. J.、 HARDSTONE J. D.、 LEWIS B. N. (IN PART)、 PALM+

  DOI：——

  日期：——
• 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.