(R)-3-(3-{(R)-1-[(1R,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide | 691012-82-5

• 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: (R)-3-(3-{(R)-1-[(1R,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide
• 英文别名: (3R)-3-[3-[(1R)-1-[(1R,5R)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-ethynylcyclopent-2-en-1-yl]prop-2-ynoxy]-2-chloro-4-methoxyphenyl]-3-[tert-butyl(dimethyl)silyl]oxy-N-[(E)-3-iodo-4-[(4-methoxyphenyl)methoxy]but-2-enyl]propanamide
• CAS: 691012-82-5
• 化学式: C₅₀H₇₅ClINO₈Si₃
• 分子量: 1064.76
• InChiKey: GTEXVFOLXCSIAT-AAJFSBAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.96
• 重原子数：
  64
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-3-(3-{(R)-1-[(1R,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以40%的产率得到(1R,8R,20R,21R)-8,20,21-tris[[tert-butyl(dimethyl)silyl]oxy]-24-chloro-4-methoxy-14-[(4-methoxyphenyl)methoxymethyl]-2-oxa-11-azapentacyclo[11.8.2.13,7.016,22.017,21]tetracosa-3,5,7(24),13(23),14,16(22),17-heptaen-10-one
  参考文献：
  名称：

  Convergent approach to the maduropeptin chromophore: aryl ether formation of (R)-3-aryl-3-hydroxypropanamide and cyclization of macrolactam

  摘要：

  Efficient enantioselective syntheses of the functionalized phenol and diethynylcyclopentene moiety of the maduropeptin chromophore were achieved. Their CsF-mediated coupling yielded a sterically congested aryl propargyl ether. The subsequent intramolecular Sonogashira coupling reaction between the vinyl iodide and diethynyl groups occurred at the appropriate position to yield a macrolactam, which was accompanied by Pd-mediated enyne-yne benzarmulation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.020
• 作为产物：
  描述：

  在 2,6-二甲基吡啶 、 四丁基氟化铵 、 一水合肼 、 三苯基膦 、 cesium fluoride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (R)-3-(3-{(R)-1-[(1R,5R)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-cyclopent-2-enyl]-prop-2-ynyloxy}-2-chloro-4-methoxy-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide
  参考文献：
  名称：

  Convergent approach to the maduropeptin chromophore: aryl ether formation of (R)-3-aryl-3-hydroxypropanamide and cyclization of macrolactam

  摘要：

  Efficient enantioselective syntheses of the functionalized phenol and diethynylcyclopentene moiety of the maduropeptin chromophore were achieved. Their CsF-mediated coupling yielded a sterically congested aryl propargyl ether. The subsequent intramolecular Sonogashira coupling reaction between the vinyl iodide and diethynyl groups occurred at the appropriate position to yield a macrolactam, which was accompanied by Pd-mediated enyne-yne benzarmulation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.020