(4R)-6-(tert-butyldimethylsiloxy)-4-methylhex-1-ene | 152755-09-4

• 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)-6-(tert-butyldimethylsiloxy)-4-methylhex-1-ene
• CAS: 152755-09-4
• 化学式: C₁₃H₂₈OSi
• 分子量: 228.45
• InChiKey: ZFVXHXMABCDXQZ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (4R)-6-(tert-butyldimethylsiloxy)-4-methylhex-1-ene 在 zirconocene dichloride 18-冠醚-6 、 potassium tert-butylate 、 溴 、 碘 作用下， 以 四氯化碳 、 正己烷 为溶剂， 反应 44.75h， 生成 (4R,1E)-6-(tert-butyldimethylsiloxy)-1-iodo-2,4-dimethylhex-1-ene
  参考文献：
  名称：

  Khandekar, Girish; Robinson, Gareth C.; Stacey, Nicholas A., Journal of the Chemical Society. Perkin transactions I, 1993, # 13, p. 1507 - 1520

  摘要：

  DOI：
• 作为产物：
  描述：

  (3R)-1-(tert-butyldimethylsiloxy)-3-methyl-6-(o-nitrophenylseleno)hexane 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到(4R)-6-(tert-butyldimethylsiloxy)-4-methylhex-1-ene
  参考文献：
  名称：

  Khandekar, Girish; Robinson, Gareth C.; Stacey, Nicholas A., Journal of the Chemical Society. Perkin transactions I, 1993, # 13, p. 1507 - 1520

  摘要：

  DOI：

文献信息

• Oxyanion Orientation in Anionic Oxy-Cope Rearrangements
  作者：Eun Lee、Yong Rok Lee、Bongjin Moon、Ohyun Kwon、Mi Seong Shim、Jae Sook Yun

  DOI：10.1021/jo00085a037

  日期：1994.3

  Efficiency of chirality transfer in anionic oxy-Cope rearrangement depends solely on the orientational preference of the oxyanionic bond in the substrates with a single carbinol carbon chiral center. In chairlike transition-state conformations for the rearrangement of simplest substrates like anions generated from (E)-1-phenyl-1,5-hexadien-3-ol and (E)-1,5-heptadien-4-ol, the oxyanionic bond is more prone to adopt the pseudoaxial orientation. On the other hand, anions generated from (E)-2-methyl-1,5-heptadien-4-ol, (E)-5-tert-butyl-1-phenyl-1,5-hexadien-3-ol, and 4-(2'-methyl-1'-cyclohexenyl)-1-buten-3-ol undergo rearrangement via chairlike transition states in which the pseudoequatorial oxyanionic bond is favored. It can thus be surmized that there is a slight stereoelectronic preference for the pseudoaxial oxyanionic bond in the chairlike transition states for the rearrangement of substrates without steric constraints. Substitution at C5 of the basic 1,5-hexadien-3-ol framework of substrates, however, leads to 1,3-diaxial steric interaction in the chairlike transition states with pseudoaxial oxyanionic bond, and pseudoequatorial disposition of oxyanionic bond becomes more favorable.
• Khandekar, Girish; Robinson, Gareth C.; Stacey, Nicholas A., Journal of the Chemical Society. Perkin transactions I, 1993, # 13, p. 1507 - 1520
  作者：Khandekar, Girish、Robinson, Gareth C.、Stacey, Nicholas A.、Thomas, Eric J.、Vather, Sunil

  DOI：——

  日期：——