12-phenyldodecyl tetrahydropyranyl ether | 502929-61-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 12-phenyldodecyl tetrahydropyranyl ether
• 英文别名: 2-(12-phenyldodecoxy)oxane
• CAS: 502929-61-5
• 化学式: C₂₃H₃₈O₂
• 分子量: 346.554
• InChiKey: SMFNCAWLGXIIAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  25.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  12-phenyldodecyl tetrahydropyranyl ether 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 12-phenyldodecan-1-ol
  参考文献：
  名称：

  通过直接金属化合成缅甸紫胶树树汁中发现的3-（ω-苯基烷基）邻苯二酚，酚类脂

  摘要：

  通过定向金属化合成3-（ω-苯基烷基）邻苯二酚。

  DOI：

  10.1039/c39860001234
• 作为产物：
  描述：

  12-(tetrahydropyran-2'-yloxy)dodecanal 在 三乙基硅烷 、 三氟乙酸 作用下， 以 乙醚 为溶剂， 生成 12-phenyldodecyl tetrahydropyranyl ether
  参考文献：
  名称：

  通过直接金属化合成缅甸紫胶树树汁中发现的3-（ω-苯基烷基）邻苯二酚，酚类脂

  摘要：

  通过定向金属化合成3-（ω-苯基烷基）邻苯二酚。

  DOI：

  10.1039/c39860001234

文献信息

• Synthesis of 3- and 4-(ω-Phenylalkyl)catechols, the Sap Exuded from a Burmese Lac Tree,<i>Melanorrhoea Usitate</i>
  作者：Tetsuo Miyakoshi、Yumin Du、Ju Kumanotani

  DOI：10.1246/bcsj.64.1054

  日期：1991.3

  The presence of 3- and 4-(ω-phenylalkyl)catechols in Burmese lac has been confirmed by their synthesis. 3-(ω-Phenylalkyl)veratroles were synthesized by alkylation of ω-phenylalkyl bromide with aryl lithium derived from veratrole. 4-(ω-Phenylalkyl)veratroles were similarly obtained from ω-phenylalkyl bromide and 4-bromoveratrole. Demethylation of 3- and 4-(ω-phenylalkyl)veratroles with boron tribromide

  缅甸紫胶中 3- 和 4-(ω-苯基烷基) 儿茶酚的存在已通过它们的合成得到证实。3-(ω-苯基烷基)藜芦醇是通过ω-苯基烷基溴与衍生自藜芦的芳基锂烷基化合成的。4-(ω-苯基烷基)藜芦醇类似地从ω-苯基烷基溴化物和4-溴代藜芦醇获得。用三溴化硼对 3- 和 4-（ω-苯基烷基）藜芦醇进行去甲基化，得到相应的儿茶酚，收率良好。
• 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.