tert-butyl-[[(5R,7S,8R,9S)-9-[(E)-5-[(4-methoxyphenyl)methoxy]-2,6,6-trimethyl-9-phenylselanylnon-1-enyl]-2,2,7-trimethyl-1,3-dioxaspiro[4.4]nonan-8-yl]oxy]-dimethylsilane | 1160556-78-4

• 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: tert-butyl-[[(5R,7S,8R,9S)-9-[(E)-5-[(4-methoxyphenyl)methoxy]-2,6,6-trimethyl-9-phenylselanylnon-1-enyl]-2,2,7-trimethyl-1,3-dioxaspiro[4.4]nonan-8-yl]oxy]-dimethylsilane
• CAS: 1160556-78-4
• 化学式: C₄₂H₆₆O₅SeSi
• 分子量: 758.029
• InChiKey: LVFYHHNZZQYDOS-AVYDWIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.13
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl-[[(5R,7S,8R,9S)-9-[(E)-5-[(4-methoxyphenyl)methoxy]-2,6,6-trimethyl-9-phenylselanylnon-1-enyl]-2,2,7-trimethyl-1,3-dioxaspiro[4.4]nonan-8-yl]oxy]-dimethylsilane 在 双氧水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以68%的产率得到tert-butyl-[[(5R,7S,8R,9S)-9-[(1E)-5-[(4-methoxyphenyl)methoxy]-2,6,6-trimethylnona-1,8-dienyl]-2,2,7-trimethyl-1,3-dioxaspiro[4.4]nonan-8-yl]oxy]-dimethylsilane
  参考文献：
  名称：

  Total Synthesis of Jatrophane Diterpenes from Euphorbia characias

  摘要：

  The enantioselective total synthesis of the jatrophane diterpene (-)-15-O-acetyl-3-O-propionylcharaciol is described. Starting from an advanced cyclopentane building block, a B-alkyl Suzuki-Miyaura cross-coupling and carbonyl addition were utilized to assemble a fully functionalized triene, and a ring-closing metathesis was then employed to construct the rigid 12-membered ring. Twenty-five years after the original report on the isolation of the natural product, our total synthesis unambiguously corroborates the original tentative structural assignment.

  DOI：

  10.1021/ol900819u
• 作为产物：
  描述：

  1-[(4,4-Dimethyl-7-phenylselanylhept-1-en-3-yl)oxymethyl]-4-methoxybenzene 、 tert-butyl-[[(5R,7S,8R,9S)-9-[(E)-2-iodoprop-1-enyl]-2,2,7-trimethyl-1,3-dioxaspiro[4.4]nonan-8-yl]oxy]-dimethylsilane 在 9-硼双环[3.3.1]壬烷 、 三苯胂 、 caesium carbonate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.08h， 以86%的产率得到tert-butyl-[[(5R,7S,8R,9S)-9-[(E)-5-[(4-methoxyphenyl)methoxy]-2,6,6-trimethyl-9-phenylselanylnon-1-enyl]-2,2,7-trimethyl-1,3-dioxaspiro[4.4]nonan-8-yl]oxy]-dimethylsilane
  参考文献：
  名称：

  Total Synthesis of Jatrophane Diterpenes from Euphorbia characias

  摘要：

  The enantioselective total synthesis of the jatrophane diterpene (-)-15-O-acetyl-3-O-propionylcharaciol is described. Starting from an advanced cyclopentane building block, a B-alkyl Suzuki-Miyaura cross-coupling and carbonyl addition were utilized to assemble a fully functionalized triene, and a ring-closing metathesis was then employed to construct the rigid 12-membered ring. Twenty-five years after the original report on the isolation of the natural product, our total synthesis unambiguously corroborates the original tentative structural assignment.

  DOI：

  10.1021/ol900819u

文献信息

• Total Synthesis of Jatrophane Diterpenes from <i>Euphorbia characias</i>
  作者：Christoph Schnabel、Martin Hiersemann

  DOI：10.1021/ol900819u

  日期：2009.6.18

  The enantioselective total synthesis of the jatrophane diterpene (-)-15-O-acetyl-3-O-propionylcharaciol is described. Starting from an advanced cyclopentane building block, a B-alkyl Suzuki-Miyaura cross-coupling and carbonyl addition were utilized to assemble a fully functionalized triene, and a ring-closing metathesis was then employed to construct the rigid 12-membered ring. Twenty-five years after the original report on the isolation of the natural product, our total synthesis unambiguously corroborates the original tentative structural assignment.