(E)-(1S,5R)-1-cyclohexyl-7-phenylhept-3-ene-1,5-diol | 1167535-03-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(1S,5R)-1-cyclohexyl-7-phenylhept-3-ene-1,5-diol
• 英文别名: (1S,3E,5R)-1-cyclohexyl-7-phenylhept-3-ene-1,5-diol
• CAS: 1167535-03-6
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: CSAXLUZRYIHBHQ-SZCOOPAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-(1S,5R)-1-cyclohexyl-7-phenylhept-3-ene-1,5-diol 、 叔丁基二甲基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到(1S,3E,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-1-cyclohexyl-7-phenylhept-3-en-1-ol
  参考文献：
  名称：

  Stereoselective Synthesis of syn,syn- and syn,anti-1,3,5-Triols via Intramolecular Hydrosilylation of Substituted Pent-3-en-1,5-diols

  摘要：

  A stereoselective method for synthesis of syn,syn- and syn,anti-1,3,5-triols based on a double allylboration-intramolecular hydrosilylation sequence has been developed. The 1,3-syn stereocontrol is achieved in the intramolecular hydrosilylation of monoprotected (Z)-1,5-syn-diols and (E)-1,5-anti-diols with 87:13 to 95:5 and 86:14 to 88:12 diastereomeric ratios, respectively, by using 0.5 mol % of Karstedt's catalyst in toluene.

  DOI：

  10.1021/ol9009877
• 作为产物：
  描述：

  苯丙醛 、 、 环己烷基甲醛 反应 2.0h， 以76%的产率得到(E)-(1S,5R)-1-cyclohexyl-7-phenylhept-3-ene-1,5-diol
  参考文献：
  名称：

  Stereoselective Synthesis of syn,syn- and syn,anti-1,3,5-Triols via Intramolecular Hydrosilylation of Substituted Pent-3-en-1,5-diols

  摘要：

  A stereoselective method for synthesis of syn,syn- and syn,anti-1,3,5-triols based on a double allylboration-intramolecular hydrosilylation sequence has been developed. The 1,3-syn stereocontrol is achieved in the intramolecular hydrosilylation of monoprotected (Z)-1,5-syn-diols and (E)-1,5-anti-diols with 87:13 to 95:5 and 86:14 to 88:12 diastereomeric ratios, respectively, by using 0.5 mol % of Karstedt's catalyst in toluene.

  DOI：

  10.1021/ol9009877

文献信息

• Concerning the Selective Protection of (<i>Z</i>)-1,5-<i>syn</i>-Ene-diols and (<i>E</i>)-1,5-<i>anti</i>-Ene-diols as Allylic Triethylsilyl Ethers
  作者：Jacqueline D. Hicks、Chan Woo Huh、Ashley D. Legg、William R. Roush

  DOI：10.1021/ol702588h

  日期：2007.12.1

  Treatment of unsaturated 1,5-diols 2 with TES-CI (1.1 equiv), imidazole, and catalytic DMAP in 1:1 CH2Cl2-DMF at -78 degrees C effects selective silylation of the allylic alcohol with > 95:5 chemoselectivity when the allylic and homoallylic alcohols are in similar steric environments.