1-hexylcyclopropyl methanesulfonate | 437709-21-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1-hexylcyclopropyl methanesulfonate
• 英文别名: (1-Hexylcyclopropyl) methanesulfonate
• CAS: 437709-21-2
• 化学式: C₁₀H₂₀O₃S
• 分子量: 220.333
• InChiKey: MEGYHYAYSVBEDY-UHFFFAOYSA-N

物化性质

• 沸点：
  325.6±9.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-hexylcyclopropyl methanesulfonate 在 蔗糖 Saccharomyces cerevisiae 、 硝酸铵 、 citric monohydrate 、 碳酸氢钠 、 碳酸氢铵 、 magnesium bromide 作用下， 以 乙醚 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 136.0h， 生成 (R)-2-methyloctan-1-ol
  参考文献：
  名称：

  The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution

  摘要：

  The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.005
• 作为产物：
  描述：

  庚酸乙酯 在 titanium(IV) isopropylate 、 硫酸 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 1-hexylcyclopropyl methanesulfonate
  参考文献：
  名称：

  The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution

  摘要：

  The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.005

文献信息

• A Simple and Efficient Conversion of Tertiary Cyclopropanols to 2-Substituted Allyl Halides
  作者：Yurii Yu. Kozyrkov、Oleg G. Kulinkovich

  DOI：10.1055/s-2002-20461

  日期：——

  tertiary cyclopropanols are converted into 2-substituted allyl bromides in high yields under the action of magnesium bromide in diethyl ether. Magnesium chloride, aluminium chloride and titanium tetrachloride also induce effectively the transformation of cyclopropyl sulphonates into the corresponding allyl chlorides.

  在二乙醚中溴化镁的作用下，容易获得的叔环丙醇磺酸盐以高产率转化为2-取代的烯丙基溴。氯化镁、氯化铝和四氯化钛也能有效地诱导环丙基磺酸盐转化为相应的烯丙基氯。
• The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution
  作者：Konstantin N. Prokhorevich、Oleg G. Kulinkovich

  DOI：10.1016/j.tetasy.2006.11.005

  日期：2006.11

  The insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate 1-Ac was prepared from diastereomerically enriched (2S*,3R*,7R)-1, which in turn was obtained by the coupling of racemic 3,4-dimethyl-gamma-butyrolactone with (7S)-2-methyloctyllithium, followed by a Wolff-Kishner reduction of the resulting ketone. Conversion of (2S*,3R*,7R)-1 to the corresponding alkyl hydrogen phthalate and diastereomer salt formation with (S)-PhCHMeNH2 provided after several crystallizations individual diastereomer, which was later transformed into target 1-Ac after hydrolysis and acylation. (c) 2006 Published by Elsevier Ltd.