(Z)-8-phenyl-7-octen-1-ol | 136066-74-5

• 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: (Z)-8-phenyl-7-octen-1-ol
• 英文别名: cis-8-phenyl-7-octenol；(Z)-8-phenyloct-7-en-1-ol
• CAS: 136066-74-5
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: IJWPFHBVSGQOCE-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  15.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  7-(2-tetrahydropyranyloxy)heptanal 在 正丁基锂 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 45.0h， 生成 (Z)-8-phenyl-7-octen-1-ol
  参考文献：
  名称：

  Intramolecular anodic olefin coupling reactions: a useful method for carbon-carbon bond formation

  摘要：

  The utility of intramolecular anodic olefin coupling reactions for effecting carbon-carbon bond formation has been examined. All of the successful cyclizations studied utilized either an alkyl or silyl enol ether as one of the participating olefins. The enol ethers could be coupled to simple alkyl olefins, styrenes, and allylsilanes in isolated yields ranging from 57 to 84%. The reactions were found to be effective for generating both five- and six-membered rings. The best conditions for cyclization utilized a reticulated vitreous carbon anode, constant-current conditions in an undivided cell, and a lithium perchlorate in either 50% methanol/tetrahydrofuran or 20% methanol/dichloromethane electrolyte solution. The use of an allylsilane as one of the participating olefins allowed for the regiospecific formation of olefinic products. In addition to the olefinic products, these reactions produced a small amount of a cyclized ether product in which the silyl group had not been eliminated. Deuterium-labeling studies showed that at least half of this ether byproduct arose from intramolecular migration of the methoxy group that was initially part of the starting enol ether to the carbon-beta to the silyl group. Intramolecular migration reactions of this type were found to participate in a number of the reported cyclization reactions.

  DOI：

  10.1021/ja00019a038

文献信息

• Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-Metastatic murine colon 26-L5 carcinoma cell line
  作者：T Nagaoka

  DOI：10.1016/s0968-0896(02)00138-4

  日期：2002.10

  Caffeic acid phenethyl ester (CAPE, 2) and its twenty analogues (1, 3-21) were prepared. These esters were tested by MTT assay on growth of murine colon 26-L5 carcinoma, murine B16-BL6 malonoma, murine Lewis lung carcinoma, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and human cervix HeLa adenocarcinoma cell lines. It was found that CAPE analogues possessed selective antiproliferative activity toward highly liver-metastatic murine colon 26-L5 carcinoma cell line. Among them, 4-phenylbutyl caffeate (4), (Z)-8-phenyl-7-octenyl (10a) and (E)-8-phenyl-7-octenyl (10b) caffeate showed the most potent antiproliferative activity (EC50 value, 0.02 muM). In addition, CAPE (2) induced DNA fragmentation at concentrations of 1 to 10 mug/mL towards murine colon 26-L5 carcinoma cells. (C) 2002 Elsevier Science Ltd. All rights reserved.