(4R)-4-((tert-butyldimethylsilyl)oxy)-2-methylhept-1-ene | 1309595-82-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4R)-4-((tert-butyldimethylsilyl)oxy)-2-methylhept-1-ene
• 英文别名: tert-butyl-dimethyl-[(4R)-2-methylhept-1-en-4-yl]oxysilane
• CAS: 1309595-82-1
• 化学式: C₁₄H₃₀OSi
• 分子量: 242.477
• InChiKey: DJSOQUPEQQUZAH-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4R)-4-((tert-butyldimethylsilyl)oxy)-2-methylhept-1-ene 、 (5S,6S,8R)-11-(benzyloxy)-6,8-bis((4-methoxybenzyl)oxy)-5-methylundec-2-en-4-one 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以45%的产率得到(4R,9S,10S,12R,E)-15-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-10,12-bis((4-methoxybenzyl)oxy)-6,9-dimethylpentadec-6-en-8-one
  参考文献：
  名称：

  Highly Demanding Cross-Metathesis in the Synthesis of the C16–C30 Fragment of Dolabelide C

  摘要：

  A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.

  DOI：

  10.1021/jo200466t
• 作为产物：
  描述：

  (R)-1,2-环氧基戊烷 在 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (4R)-4-((tert-butyldimethylsilyl)oxy)-2-methylhept-1-ene
  参考文献：
  名称：

  Highly Demanding Cross-Metathesis in the Synthesis of the C16–C30 Fragment of Dolabelide C

  摘要：

  A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.

  DOI：

  10.1021/jo200466t

文献信息

• Highly Demanding Cross-Metathesis in the Synthesis of the C16–C30 Fragment of Dolabelide C
  作者：Marie-Gabrielle Braun、Aurélie Vincent、Mehdi Boumediene、Joëlle Prunet

  DOI：10.1021/jo200466t

  日期：2011.6.17

  A highly demanding cross-metathesis (CM) reaction for the formation of the C24-C25 trisubstituted olefin of dolabelide C has been optimized. A difference in reactivity between the E and Z enone isomers in this reaction was uncovered, and the selection of the Z isomer of the starting enone was critical for the success of the cross-metathesis. Application to the synthesis of the C16-C30 fragment of dolabelide C is reported.