(E)-5-methylidene-7-phenylmethoxyhept-2-en-1-ol | 208658-91-7

• 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)-5-methylidene-7-phenylmethoxyhept-2-en-1-ol
• CAS: 208658-91-7
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: LUKNQZOQWMSYCA-AATRIKPKSA-N

物化性质

• 沸点：
  357.1±42.0 °C(Predicted)
• 密度：
  1.009±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-5-methylidene-7-phenylmethoxyhept-2-en-1-ol 在 titanium(IV) isopropylate 叔丁基过氧化氢 、 4 A molecular sieve 、 tetrabutylammonium bifluoride 、 (-)-diethyl tartrate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2S,3R)-5-[2-(benzyloxy)ethyl]-2-fluoro-5-hexene-1,3-diol
  参考文献：
  名称：

  Catalytic asymmetric synthesis and anticancer effects of the novel non-calcemic analog of vitamin D, 2α-fluoro-19-nor-22-oxa-1α,25-dihydroxyvitamin D3 in metastatic lung carcinoma

  摘要：

  1 alpha,25-Dihydroxyvitamin D-3 (1 alpha,25-D-3) has potent antiproliferative and anti-invasive properties in vitro in cancer cells. However, the major limitation to its clinical use is that it causes hypercalcemia. Therefore, vitamin D analogs with potent cell regulatory effects but with weaker calcemic effects than 1 alpha,25-D-3 are required. Among them, 22-oxa-1 alpha,25-D-3 and 19-nor-1 alpha,25-D-3 have anti-cancer effects with relatively low calcemic effects. Modifications at the C-2ot position of the A-ring also produced analogs with a unique biological profile. Not only the side-chain but also the A-ring modification thus generates a unique analog with potent cell regulatory effects and low calcemic activity as well. We report here that the hybrid 1 alpha,25-D-3 analog, synthesized via the highly regio- and stereo-selective ring opening 2 alpha-fluorination and catalytic asymmetric carbonyl-ene cyclization, with 2 alpha-fluoro, 19-nor, and 22-oxa modification exhibits unique cell regulatory activities against the development of metastatic lung carcinoma. (c) 2007 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2007.03.002
• 作为产物：
  描述：

  (((3-methylbut-3-en-1-yl)oxy)methyl)benzene 在 二氯乙基铝 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-5-methylidene-7-phenylmethoxyhept-2-en-1-ol
  参考文献：
  名称：

  Catalytic asymmetric synthesis and anticancer effects of the novel non-calcemic analog of vitamin D, 2α-fluoro-19-nor-22-oxa-1α,25-dihydroxyvitamin D3 in metastatic lung carcinoma

  摘要：

  1 alpha,25-Dihydroxyvitamin D-3 (1 alpha,25-D-3) has potent antiproliferative and anti-invasive properties in vitro in cancer cells. However, the major limitation to its clinical use is that it causes hypercalcemia. Therefore, vitamin D analogs with potent cell regulatory effects but with weaker calcemic effects than 1 alpha,25-D-3 are required. Among them, 22-oxa-1 alpha,25-D-3 and 19-nor-1 alpha,25-D-3 have anti-cancer effects with relatively low calcemic effects. Modifications at the C-2ot position of the A-ring also produced analogs with a unique biological profile. Not only the side-chain but also the A-ring modification thus generates a unique analog with potent cell regulatory effects and low calcemic activity as well. We report here that the hybrid 1 alpha,25-D-3 analog, synthesized via the highly regio- and stereo-selective ring opening 2 alpha-fluorination and catalytic asymmetric carbonyl-ene cyclization, with 2 alpha-fluoro, 19-nor, and 22-oxa modification exhibits unique cell regulatory activities against the development of metastatic lung carcinoma. (c) 2007 Published by Elsevier B.V.

  DOI：

  10.1016/j.jfluchem.2007.03.002

文献信息

• Asymmetric synthesis of a key ring A synthon for 1α-hydroxy-19-nor vitamin D
  作者：Lawrence F. Courtney、Meinolf Lange、Milan R. Uskoković、Peter M. Wovkulich

  DOI：10.1016/s0040-4039(98)00682-0

  日期：1998.5

  A diasteroselective carbonyl ene reaction on a substrate obtained from a regioselective propiolate ene reaction is described for the synthesis of 19-nor A-ring synthon 3. (C) 1998 Elsevier Science Ltd. All rights reserved.