3-[(1S,2R)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2-isoquinolinio]propyl-1-sulfate | 213999-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 3-[(1S,2R)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2-isoquinolinio]propyl-1-sulfate
• 英文别名: 3-[(1S,2R)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxyphenyl)-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propyl sulfate
• CAS: 213999-54-3
• 化学式: C₂₄H₃₃NO₉S
• 分子量: 511.593
• InChiKey: LJRQIWQSSFHPKA-ZCYQVOJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-[(1S,2R)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2-isoquinolinio]propyl-1-sulfate 在 甲醇 、 乙酰氯 作用下， 反应 6.0h， 以98%的产率得到(1S,2R)-6,7-dimethoxy-2-(3-hydroxypropyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydroisoquinolinium chloride
  参考文献：
  名称：

  Synthesis of Ultra-Short-Acting Neuromuscular Blocker GW 0430:  A Remarkably Stereo- and Regioselective Synthesis of Mixed Tetrahydroisoquinolinium Chlorofumarates

  摘要：

  [GRAPHICS]The stereo- and regioselective synthesis of ultra-short-acting nondepolarizing neuromuscular blocker GW 0430 (5a) is described. Key steps involved the enantioselective transfer hydrogenation of imine 8 employing Noyori's catalyst, the stereoselective crystallization and methanolysis of trans-betaines 11 and 12, and the stereo- and regioselective trans elimination of hydrogen chloride from 14, The latter transformation allowed complete control of the position of the chloro substituent and stereochemistry at the double bond of the linker in 15.

  DOI：

  10.1021/ol9911573
• 作为产物：
  描述：

  (1S)-6,7-dimethoxy-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydroisoquinolinium formate 在 甲酸 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 3-[(1S,2R)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-2-isoquinolinio]propyl-1-sulfate
  参考文献：
  名称：

  Synthesis of Ultra-Short-Acting Neuromuscular Blocker GW 0430:  A Remarkably Stereo- and Regioselective Synthesis of Mixed Tetrahydroisoquinolinium Chlorofumarates

  摘要：

  [GRAPHICS]The stereo- and regioselective synthesis of ultra-short-acting nondepolarizing neuromuscular blocker GW 0430 (5a) is described. Key steps involved the enantioselective transfer hydrogenation of imine 8 employing Noyori's catalyst, the stereoselective crystallization and methanolysis of trans-betaines 11 and 12, and the stereo- and regioselective trans elimination of hydrogen chloride from 14, The latter transformation allowed complete control of the position of the chloro substituent and stereochemistry at the double bond of the linker in 15.

  DOI：

  10.1021/ol9911573

文献信息

• Org Lett. 1999, 1, 1993-1996
  作者：

  DOI：——

  日期：——
• Synthesis of Ultra-Short-Acting Neuromuscular Blocker GW 0430:  A Remarkably Stereo- and Regioselective Synthesis of Mixed Tetrahydroisoquinolinium Chlorofumarates
  作者：Vicente Samano、John A. Ray、James B. Thompson、Robert A. Mook、David K. Jung、Cecilia S. Koble、Michael T. Martin、Eric C. Bigham、Craig S. Regitz、Paul L. Feldman、Eric E. Boros

  DOI：10.1021/ol9911573

  日期：1999.12.1

  [GRAPHICS]The stereo- and regioselective synthesis of ultra-short-acting nondepolarizing neuromuscular blocker GW 0430 (5a) is described. Key steps involved the enantioselective transfer hydrogenation of imine 8 employing Noyori's catalyst, the stereoselective crystallization and methanolysis of trans-betaines 11 and 12, and the stereo- and regioselective trans elimination of hydrogen chloride from 14, The latter transformation allowed complete control of the position of the chloro substituent and stereochemistry at the double bond of the linker in 15.