vibsanin F | 609844-64-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: vibsanin F
• 英文别名: [(1S,4E,7S,8E,11S)-7,11-dimethyl-7-(4-methylpent-3-enyl)-12-oxabicyclo[9.1.0]dodeca-4,8-dien-4-yl]methanol
• CAS: 609844-64-6
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: KUZQLAIQYSJYPN-FUAAYOAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  vibsanin F 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到(3E,7E)-(1R,5S)-8-Hydroxymethyl-1,5-dimethyl-5-(4-methyl-pent-3-enyl)-cycloundeca-3,7-dienol
  参考文献：
  名称：

  Determination of the absolute configuration of vibsanin F by asymmetric synthesis via π-allylpalladium complex

  摘要：

  The absolute configuration of vibsanin F (1), one of the simplest 11-membered ring vibsane-type diterpene, was established to be 6R, 7S and 11S by asymmetric synthesis. A diastereomer (1a) with a 6S, 7S and 11S configuration was synthesized starting from myrcene by procedures featuring a Sharpless asymmetric epoxidation and a high diastereoselective eleven-membered ring formation between a pi-allylpalladium complex and a beta-ketoester nucleophile. Subsequent reduction of epoxide in la with LiAlH4 gave a diol, which was identical with that derived from vibsanin F. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01537-5
• 作为产物：
  描述：

  5-碘-2-甲基戊-2-烯 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 N,N-二甲基丙烯基脲 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 cerium(III) chloride 、 15-冠醚-5 、 偶氮二异丁腈 、 四丁基氟化铵 、 sodium hydride 、 苯硫酚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 甲苯 、 苯 为溶剂， 生成 vibsanin F
  参考文献：
  名称：

  Determination of the absolute configuration of vibsanin F by asymmetric synthesis via π-allylpalladium complex

  摘要：

  The absolute configuration of vibsanin F (1), one of the simplest 11-membered ring vibsane-type diterpene, was established to be 6R, 7S and 11S by asymmetric synthesis. A diastereomer (1a) with a 6S, 7S and 11S configuration was synthesized starting from myrcene by procedures featuring a Sharpless asymmetric epoxidation and a high diastereoselective eleven-membered ring formation between a pi-allylpalladium complex and a beta-ketoester nucleophile. Subsequent reduction of epoxide in la with LiAlH4 gave a diol, which was identical with that derived from vibsanin F. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01537-5

文献信息

• Determination of the absolute configuration of vibsanin F by asymmetric synthesis via π-allylpalladium complex
  作者：Hiroaki Yuasa、Gouki Makado、Yoshiyasu Fukuyama

  DOI：10.1016/s0040-4039(03)01537-5

  日期：2003.8

  The absolute configuration of vibsanin F (1), one of the simplest 11-membered ring vibsane-type diterpene, was established to be 6R, 7S and 11S by asymmetric synthesis. A diastereomer (1a) with a 6S, 7S and 11S configuration was synthesized starting from myrcene by procedures featuring a Sharpless asymmetric epoxidation and a high diastereoselective eleven-membered ring formation between a pi-allylpalladium complex and a beta-ketoester nucleophile. Subsequent reduction of epoxide in la with LiAlH4 gave a diol, which was identical with that derived from vibsanin F. (C) 2003 Elsevier Ltd. All rights reserved.