(+)-[2S,1'S,2'S]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2,4-bis(3,4-dimethoxyphenyl)butanamide | 274911-07-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (+)-[2S,1'S,2'S]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2,4-bis(3,4-dimethoxyphenyl)butanamide
• 英文别名: (2S)-2,4-bis(3,4-dimethoxyphenyl)-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylbutanamide
• CAS: 274911-07-8
• 化学式: C₃₀H₃₇NO₆
• 分子量: 507.627
• InChiKey: ZXWNZGAXVBMMED-WMQVBLFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-[2S,1'S,2'S]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2,4-bis(3,4-dimethoxyphenyl)butanamide 在 sodium tetrahydroborate 、 三氯化铝 、 氯化亚砜 、 硫酸 、 四氯化钛 、 三乙胺 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 10.0h， 生成 (+)-(1R,2S)-N-benzyl-6,7-dimethoxy-2-(3,4-dimethoxyphenyl)-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
• 作为产物：
  描述：

  4-(2-碘乙基)-1,2-二甲氧基苯 、 2-(3,4-dimethoxyphenyl)-N-[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-N-methylacetamide 在 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 以85%的产率得到(+)-[2S,1'S,2'S]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2,4-bis(3,4-dimethoxyphenyl)butanamide
  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.