(2E,6Z)-7-allyl-3,11-dimethyldodeca-2,6,10-trien-1-ol | 463964-75-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2E,6Z)-7-allyl-3,11-dimethyldodeca-2,6,10-trien-1-ol
• 英文别名: 3,11-dimethyl-7-allyl-dodeca-2(E),6(Z),10-trien-1-ol；(2E,6Z)-3,11-dimethyl-7-prop-2-enyldodeca-2,6,10-trien-1-ol
• CAS: 463964-75-2
• 化学式: C₁₇H₂₈O
• 分子量: 248.409
• InChiKey: KHBUSZHQOZCGJC-JSHGDNENSA-N

物化性质

• 沸点：
  353.4±11.0 °C(Predicted)
• 密度：
  0.880±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,6Z)-7-allyl-3,11-dimethyldodeca-2,6,10-trien-1-ol 在 N-氯代丁二酰亚胺 、 二甲基硫 、 tris(tetra-n-butylammonium) hydrogen pyrophosphate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.5h， 生成 (2E,6Z)-7-allyl-3,11-dimethyldodeca-2,6,10-trienyl diphosphate
  参考文献：
  名称：

  Synthesis of 7-Substituted Farnesyl Diphosphate Analogues

  摘要：

  [GRAPHICS]Six farnesyl diphosphate analogues modified in the central isoprene unit have been prepared via our stereoselective vinyl triflate-mediated route to isoprenoids. The 7-allyl compound 6 is a modest inhibitor of mammalian protein-farnesyl transferase, but surprisingly the other five analogues are effective alternative substrates for this enzyme.

  DOI：

  10.1021/ol026176i
• 作为产物：
  描述：

  环丙甲基酮 在 咪唑 、 四丁基氟化铵 、 碘 、 叔丁基锂 、 三苯基膦 、 zinc dibromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (2E,6Z)-7-allyl-3,11-dimethyldodeca-2,6,10-trien-1-ol
  参考文献：
  名称：

  New Synthetic Methodology for the Construction of 7-Substituted Farnesyl Diphosphate Analogs

  摘要：

  Through the use of a 1,2-metalate rearrangement, six 7-substituted farnesol analogs were generated in a concise manner. This new synthetic route allowed us to quickly prepare several diverse farnesyl diphosphate analogs with interesting biological activities against mammalian protein-farnesyl transferase.

  DOI：

  10.1021/ol201069x

文献信息

• Synthesis of 7-Substituted Farnesyl Diphosphate Analogues
  作者：Diwan S. Rawat、Richard A. Gibbs

  DOI：10.1021/ol026176i

  日期：2002.9.1

  [GRAPHICS]Six farnesyl diphosphate analogues modified in the central isoprene unit have been prepared via our stereoselective vinyl triflate-mediated route to isoprenoids. The 7-allyl compound 6 is a modest inhibitor of mammalian protein-farnesyl transferase, but surprisingly the other five analogues are effective alternative substrates for this enzyme.
• New Synthetic Methodology for the Construction of 7-Substituted Farnesyl Diphosphate Analogs
  作者：Andrew T. Placzek、Richard A. Gibbs

  DOI：10.1021/ol201069x

  日期：2011.7.15

  Through the use of a 1,2-metalate rearrangement, six 7-substituted farnesol analogs were generated in a concise manner. This new synthetic route allowed us to quickly prepare several diverse farnesyl diphosphate analogs with interesting biological activities against mammalian protein-farnesyl transferase.