2-<3-(4-Methylpent-3-enyl)-2,4-dioxaspiro<5.5>undecan-3-yl>ethanol | 137482-57-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-<3-(4-Methylpent-3-enyl)-2,4-dioxaspiro<5.5>undecan-3-yl>ethanol
• 英文别名: 2-[3-(4-methylpent-3-enyl)-2,4-dioxaspiro[5.5]undecan-3-yl]ethanol
• CAS: 137482-57-6
• 化学式: C₁₇H₃₀O₃
• 分子量: 282.423
• InChiKey: IANHCWFFCRNSHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-<3-(4-Methylpent-3-enyl)-2,4-dioxaspiro<5.5>undecan-3-yl>ethanol 在 tris(triphenylphosphine)rhodium(l) chloride sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 生成 (2S,3R)-3-Isopropenyl-7,16-dioxa-dispiro[5.2.5.2]hexadecan-2-ol
  参考文献：
  名称：

  Rh^I-catalysed formation of two conformational diastereoisomers due to a cis-cyclohexane-1,2-diol moiety. X-Ray molecular structure of two stereoisomers of 4′-isopropenyl-7,9-dioxabicyclo[4.3.0]nonane-8-spirocyclohexan-3′-yl p-bromobenzoate

  摘要：

  It is well known that cis-cyclohexane-1,2-diol and its mirror image are not superposable, but that these isomers are rapidly interconvertible by flipping from one chair conformation to the other. That is they exist as a pair of conformational enantiomers. Two aldehydes, 2-[8-(4-methylpent-3-enyl)-7,9-dioxabicyclononan-8-yl]ethanals, with the cis-cyclohexane-1,2-dioxy function at C(3) are cyclized by a Rh1 (Wilkinson) complex to give two conformational diastereoisomers due to the alcohol yielded trans-3-hydroxy-4-isopropenylcyclohexanone and cis-cyclohexane-1,2-diol after deprotection with 5% aq. AcOH. Unambiguous stereochemistry of two of the parent alcohols was determined by X-ray crystallographic analysis of their p-bromobenzoates. The stereochemistry of the 1,3-dioxolane ring, including C(1) and C(2) of the cis-cyclohexane-1,2-diol and C(1') of the trans-3-hydroxy-4-isopropenylcyclohexanone, was C(1')-axial-O-axial-C(1) and C(1')-equatorial-O-equatorial-C(2) for the two title compounds, and C(1')-axial-O-equatorial-C(1) and C(1')-equatorial-O-axial-C(2) for the other pair of isomers.

  DOI：

  10.1039/p19910002531
• 作为产物：
  描述：

  methyl 7-methyl-3-oxooct-6-enoate 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 15.0h， 生成 2-<3-(4-Methylpent-3-enyl)-2,4-dioxaspiro<5.5>undecan-3-yl>ethanol
  参考文献：
  名称：

  Rh^I-catalysed formation of two conformational diastereoisomers due to a cis-cyclohexane-1,2-diol moiety. X-Ray molecular structure of two stereoisomers of 4′-isopropenyl-7,9-dioxabicyclo[4.3.0]nonane-8-spirocyclohexan-3′-yl p-bromobenzoate

  摘要：

  It is well known that cis-cyclohexane-1,2-diol and its mirror image are not superposable, but that these isomers are rapidly interconvertible by flipping from one chair conformation to the other. That is they exist as a pair of conformational enantiomers. Two aldehydes, 2-[8-(4-methylpent-3-enyl)-7,9-dioxabicyclononan-8-yl]ethanals, with the cis-cyclohexane-1,2-dioxy function at C(3) are cyclized by a Rh1 (Wilkinson) complex to give two conformational diastereoisomers due to the alcohol yielded trans-3-hydroxy-4-isopropenylcyclohexanone and cis-cyclohexane-1,2-diol after deprotection with 5% aq. AcOH. Unambiguous stereochemistry of two of the parent alcohols was determined by X-ray crystallographic analysis of their p-bromobenzoates. The stereochemistry of the 1,3-dioxolane ring, including C(1) and C(2) of the cis-cyclohexane-1,2-diol and C(1') of the trans-3-hydroxy-4-isopropenylcyclohexanone, was C(1')-axial-O-axial-C(1) and C(1')-equatorial-O-equatorial-C(2) for the two title compounds, and C(1')-axial-O-equatorial-C(1) and C(1')-equatorial-O-axial-C(2) for the other pair of isomers.

  DOI：

  10.1039/p19910002531