(2R,3S)-3-methylpent-4-ene-2,3-diol | 1191425-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-3-methylpent-4-ene-2,3-diol
• CAS: 1191425-39-4
• 化学式: C₆H₁₂O₂
• 分子量: 116.16
• InChiKey: AYNRLKALDRMVQV-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-methylpent-4-ene-2,3-diol 、 2-(三苯基膦亚基)丙酸甲酯 、 丙烯醛 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 9.0h， 以76%的产率得到epicitreodiol, <6S, 7R>-6,7-dihydroxy-2,6-dimethyloct-2,4-dienoic acid methyl ester
  参考文献：
  名称：

  Silyl-Substituted Spirodiepoxides: Stereoselective Formation and Regioselective Opening

  摘要：

  A short synthesis of the natural product epi-citreodiol and the method developed to gain access to this target are described. Key advances focus on silyl substituted allenes. Upon exposure to dimethyldioxirane, spirodiepoxides form with high face selectivity and subsequently react at the silyl terminus.

  DOI：

  10.1021/ol901948d
• 作为产物：
  描述：

  、 甲基锂 在 四丁基氟化铵 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 3.0h， 以171.5 mg的产率得到(2R,3S)-3-methylpent-4-ene-2,3-diol
  参考文献：
  名称：

  Silyl-Substituted Spirodiepoxides: Stereoselective Formation and Regioselective Opening

  摘要：

  A short synthesis of the natural product epi-citreodiol and the method developed to gain access to this target are described. Key advances focus on silyl substituted allenes. Upon exposure to dimethyldioxirane, spirodiepoxides form with high face selectivity and subsequently react at the silyl terminus.

  DOI：

  10.1021/ol901948d

文献信息

• Silyl-Substituted Spirodiepoxides: Stereoselective Formation and Regioselective Opening
  作者：Partha Ghosh、Joseph R. Cusick、Jennifer Inghrim、Lawrence J. Williams

  DOI：10.1021/ol901948d

  日期：2009.10.15

  A short synthesis of the natural product epi-citreodiol and the method developed to gain access to this target are described. Key advances focus on silyl substituted allenes. Upon exposure to dimethyldioxirane, spirodiepoxides form with high face selectivity and subsequently react at the silyl terminus.