1-((8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6Hcyclopenta[a]phenanthren-17-yl)-5-phenylpenta-1,4-diyn-3-one | 1430234-92-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 1-((8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6Hcyclopenta[a]phenanthren-17-yl)-5-phenylpenta-1,4-diyn-3-one
• 英文别名: 1-[(8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-5-phenylpenta-1,4-diyn-3-one
• CAS: 1430234-92-6
• 化学式: C₃₁H₃₂O₃
• 分子量: 452.593
• InChiKey: WGQNTAZFXQCEHE-YOGXEWEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-((8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6Hcyclopenta[a]phenanthren-17-yl)-5-phenylpenta-1,4-diyn-3-one 在 1,1'-双(二苯基膦)二茂铁 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 氯苯 作用下， 反应 24.5h， 以90%的产率得到(8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-17-(phenylbuta-1,3-diyn-1-yl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene
  参考文献：
  名称：

  Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

  摘要：

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

  DOI：

  10.1021/ol400815y
• 作为产物：
  描述：

  炔雌醇 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成 1-((8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6Hcyclopenta[a]phenanthren-17-yl)-5-phenylpenta-1,4-diyn-3-one
  参考文献：
  名称：

  Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes

  摘要：

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.

  DOI：

  10.1021/ol400815y

文献信息

• Rh(I)-Catalyzed Decarbonylation of Diynones via C–C Activation: Orthogonal Synthesis of Conjugated Diynes
  作者：Alpay Dermenci、Rachel E. Whittaker、Guangbin Dong

  DOI：10.1021/ol400815y

  日期：2013.5.3

  Utilization of C-C bond activation as a unique mode of reactivity for constructing C-C bonds provides new strategies for preparing important organic molecules. Development of a Rh(I)-catalyzed C-C activation of diynones to synthesize symmetrical and unsymmetrical conjugated diynes through decarbonylation is reported. This C-C cleavage strategy takes advantage of the innate reactivity of conjugated ynones without relying on any ring strain or auxiliary directing group. This alkynation method also has orthogonal properties compared to typical cross-coupling reactions.