(+)-(S)-2-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)butanoic acid | 274911-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(S)-2-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)butanoic acid
• CAS: 274911-20-5
• 化学式: C₁₉H₂₀O₆
• 分子量: 344.364
• InChiKey: NJXPVUKNVPYQPP-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+)-(S)-2-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)butanoic acid 在 sodium tetrahydroborate 、 氯化亚砜 、 四氯化钛 、 四氯化锡 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 (+)-(1R,2S)-N-benzyl-6,7-methylenedioxy-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：

  (+)-[2S,1'S,2'S]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)butanamide 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以90%的产率得到(+)-(S)-2-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)butanoic acid
  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.