tert-butyl (R)-(2-(4-methoxyphenyl)allyl)(1-(naphthalen-1-yl)ethyl)carbamate | 1601479-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: tert-butyl (R)-(2-(4-methoxyphenyl)allyl)(1-(naphthalen-1-yl)ethyl)carbamate
• CAS: 1601479-73-5
• 化学式: C₂₇H₃₁NO₃
• 分子量: 417.548
• InChiKey: GZZJZEISZAVFCU-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.86
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (R)-N-(1-(naphthalen-1-yl)ethyl)prop-2-en-1-amine 在 4-二甲氨基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium acetate 作用下， 以 苯甲腈 、 乙腈 为溶剂， 反应 3.0h， 生成 tert-butyl (R,E)-(3-(4-methoxyphenyl)allyl)(1-(naphthalen-1-yl)ethyl)carbamate 、 tert-butyl (R)-(2-(4-methoxyphenyl)allyl)(1-(naphthalen-1-yl)ethyl)carbamate
  参考文献：
  名称：

  Construction of 3-arylpropylamines using Heck arylations. The total synthesis of cinacalcet hydrochloride, alverine, and tolpropamine

  摘要：

  New synthetic routes toward the commercial drugs cinacalcet hydrochloride, alverine, and tolpropamine were developed using a Heck-Matsuda arylation as the key-step. Several reaction conditions were evaluated for the Heck-Matsuda reaction using allylamine derivatives and arenediazonium salts. For cinacalcet hydrochloride, N-formylamide provided the best result, furnishing the synthetic target in a very high overall yield (75% over five steps). For alverine, the best results were obtained using a double Heck-Matsuda strategy, providing alverine in an excellent overall yield (69%) from N-acetyl diallylamine in three steps. Tolpropamine was synthesized in a 46% yield over five steps using an efficient reductive Heck-Matsuda arylation between p-bromo-methylcinnamate with 3-chloro tolyldiazonium salt, generating the beta,beta-diaryl propionate that was converted to tolpropamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.014