3-methyl-2(R),3(R)-epoxy-5-hexen-1-ol | 134360-83-1

• 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: 3-methyl-2(R),3(R)-epoxy-5-hexen-1-ol
• 英文别名: [(2R,3S)-3-methyl-3-prop-2-enyloxiran-2-yl]methanol
• CAS: 134360-83-1
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: VXEBRYZFGAFRPA-RQJHMYQMSA-N

物化性质

• 沸点：
  175.2±13.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  9.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-methyl-2(R),3(R)-epoxy-5-hexen-1-ol 在 lithium aluminium tetrahydride 、 1,5-二氮杂双环[4.3.0]壬-5-烯 、 碘 、 碳酸氢钠 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 30.5h， 生成 (4S)-4-methyl-2-methylideneoxan-4-ol
  参考文献：
  名称：

  Synthesis of (S)-(+)-mevalonolactone and mevalonate analogs

  摘要：

  Tetrahydropyran (R/S)-1, a vinylidene analogue of mevalonolactone, was prepared by addition of excess allyl Grignard to 4-acetoxy-2-butanone, iodoetherification of the resultant diol 5, and DBN-mediated dehydrohalogenation. Sharpless asymmetric epoxidation of 3-methylhexa-2,5-dien-1-ol (9) gave epoxide 10 that was reduced to diol 11 (> 95% ee) by LiA1H4. Annulation and elimination of HI as described for 5 furnished (S)-1. Ozonolysis of (S)-1 yielded (S)-mevalonolactone (2), whereas bromomethoxylation and controlled hydrolysis led to 3, a reactive analogue of (S)-mevalonic acid. Analogue 4, a nonionizable lipophilic version of (S)-mevalonic acid, was generated upon exposure of (S)-1 or 2 to excess Tebbe-Grubbs reagent.

  DOI：

  10.1021/jo00013a030
• 作为产物：
  描述：

  3-methyl-2(E),5-hexadien-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 D-(-)-酒石酸二乙酯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.0h， 以98%的产率得到3-methyl-2(R),3(R)-epoxy-5-hexen-1-ol
  参考文献：
  名称：

  Synthesis of (S)-(+)-mevalonolactone and mevalonate analogs

  摘要：

  Tetrahydropyran (R/S)-1, a vinylidene analogue of mevalonolactone, was prepared by addition of excess allyl Grignard to 4-acetoxy-2-butanone, iodoetherification of the resultant diol 5, and DBN-mediated dehydrohalogenation. Sharpless asymmetric epoxidation of 3-methylhexa-2,5-dien-1-ol (9) gave epoxide 10 that was reduced to diol 11 (> 95% ee) by LiA1H4. Annulation and elimination of HI as described for 5 furnished (S)-1. Ozonolysis of (S)-1 yielded (S)-mevalonolactone (2), whereas bromomethoxylation and controlled hydrolysis led to 3, a reactive analogue of (S)-mevalonic acid. Analogue 4, a nonionizable lipophilic version of (S)-mevalonic acid, was generated upon exposure of (S)-1 or 2 to excess Tebbe-Grubbs reagent.

  DOI：

  10.1021/jo00013a030