(+)-(1R,2S)-N-benzyl-6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-1-naphthylamine | 274911-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+)-(1R,2S)-N-benzyl-6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-1-naphthylamine
• CAS: 274911-24-9
• 化学式: C₂₈H₃₃NO₅
• 分子量: 463.574
• InChiKey: XQZDUFQJNQXQAG-KDYSTLNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.18
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (+)-(1R,2S)-N-benzyl-6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-1-naphthylamine 在 盐酸 作用下， 反应 16.0h， 以94%的产率得到(-)-(4bR,10bS)-N-benzyl-4b,5,6,10b,11,12-hexahydro-2,3,7,8,9-pentamethoxybenzo[c]phenanthridine
  参考文献：
  名称：

  Stereocontrolled synthesis of 2-aryl tetralones. Application in the synthesis of B/C hexahydrobenzo[c]phenanthridine alkaloids

  摘要：

  Hexahydrobenzo[c]phenanthridines possessing a B/C cis ring junction have been synthesized in a stereoselective way starting from chiral non-racemic 2-aryl-tetralones prepared by asymmetric alkylation of (+)-(S,S)-pseudoephedrine based arylacetamide enolates with appropriately functionalized 2-aryl-1-iodoethane electrophiles. Subsequent transformations (intramolecular Friedel-Crafts acylation, stereocontrolled reductive amination and Pictet-Spengler cyclization) yielded the target heterocycles in good overall yields and in excellent stereoselectivities. (C) 2000 Elsevier Science Ltd. AU rights reserved.

  DOI：

  10.1016/s0957-4166(00)00042-2
• 作为产物：
  描述：

  4-(2-碘乙基)-1,2-二甲氧基苯 在 sodium tetrahydroborate 、 三氯化铝 、 氯化亚砜 、 硫酸 、 四氯化钛 、 三乙胺 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.25h， 生成 (+)-(1R,2S)-N-benzyl-6,7-dimethoxy-2-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydro-1-naphthylamine
  参考文献：
  名称：

  Stereocontrolled synthesis of 2-aryl tetralones. Application in the synthesis of B/C hexahydrobenzo[c]phenanthridine alkaloids

  摘要：

  Hexahydrobenzo[c]phenanthridines possessing a B/C cis ring junction have been synthesized in a stereoselective way starting from chiral non-racemic 2-aryl-tetralones prepared by asymmetric alkylation of (+)-(S,S)-pseudoephedrine based arylacetamide enolates with appropriately functionalized 2-aryl-1-iodoethane electrophiles. Subsequent transformations (intramolecular Friedel-Crafts acylation, stereocontrolled reductive amination and Pictet-Spengler cyclization) yielded the target heterocycles in good overall yields and in excellent stereoselectivities. (C) 2000 Elsevier Science Ltd. AU rights reserved.

  DOI：

  10.1016/s0957-4166(00)00042-2

文献信息

• Stereocontrolled synthesis of 2-aryl tetralones. Application in the synthesis of B/C hexahydrobenzo[c]phenanthridine alkaloids
  作者：Jose L Vicario、Dolores Badı́a、Esther Domı́nguez、Luisa Carrillo

  DOI：10.1016/s0957-4166(00)00042-2

  日期：2000.3

  Hexahydrobenzo[c]phenanthridines possessing a B/C cis ring junction have been synthesized in a stereoselective way starting from chiral non-racemic 2-aryl-tetralones prepared by asymmetric alkylation of (+)-(S,S)-pseudoephedrine based arylacetamide enolates with appropriately functionalized 2-aryl-1-iodoethane electrophiles. Subsequent transformations (intramolecular Friedel-Crafts acylation, stereocontrolled reductive amination and Pictet-Spengler cyclization) yielded the target heterocycles in good overall yields and in excellent stereoselectivities. (C) 2000 Elsevier Science Ltd. AU rights reserved.