(E)-(S)-1-Cyclohexyl-hexa-1,5-dien-3-ol | 873316-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(S)-1-Cyclohexyl-hexa-1,5-dien-3-ol
• CAS: 873316-20-2
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: OVEVXUQOPBAILH-VMPCVLLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-(S)-1-Cyclohexyl-hexa-1,5-dien-3-ol 在 Grubbs catalyst first generation 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S,E)-6-(2-cyclohexylvinyl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Cytotoxic activity of (S)-goniothalamin and analogues against human cancer cells

  摘要：

  (R)- and (S)-Goniothalamin (1) and analogues 2-9 were efficiently prepared in high overall yield and enantiomeric purity, and their cytotoxic activities were evaluated against eight human cancer cell lines. A structure-activity relationship study (SAR) allowed us to establish the relevant structural features for the cytotoxic activity of goniothalamin analogues. In addition, we have identified non-natural form of goniothalamin (S)-1 and analogue 5 as the highest and more selective cytotoxic compounds against kidney cancer cell growth (786-0) with IC50 = 4 and 5 nM, respectively, and compound 8 (IC50 = 4 nM) as the more potent against breast cancer cells with resistance phenotype for adryamycin (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.036
• 作为产物：
  描述：

  乙烯基环己烷 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 13.33h， 生成 (E)-(S)-1-Cyclohexyl-hexa-1,5-dien-3-ol 、
  参考文献：
  名称：

  Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis

  摘要：

  The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g.. Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.080