Methyl 2-<1βH,6βH-8α-(4-Methylpent-3-enyl)-7,9-dioxabicyclo<4.3.0>nonan-8β-yl>acetate | 126890-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Methyl 2-<1βH,6βH-8α-(4-Methylpent-3-enyl)-7,9-dioxabicyclo<4.3.0>nonan-8β-yl>acetate
• CAS: 126890-27-5
• 化学式: C₁₆H₂₆O₄
• 分子量: 282.38
• InChiKey: JWQYIYXHPNRWQE-FOLVSLTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 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：
  0.81
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Methyl 2-<1βH,6βH-8α-(4-Methylpent-3-enyl)-7,9-dioxabicyclo<4.3.0>nonan-8β-yl>acetate 在 lithium aluminium tetrahydride 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 2-<1βH,6βH-8α-(4-Methylpent-3-enyl)-7,9-dioxabicyclo<4.3.0>nonan-8β-yl>ethanal
  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：

  cis-1,2-cyclohexane 、 methyl 7-methyl-3-oxooct-6-enoate 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 12.0h， 以37%的产率得到Methyl 2-<1αH,6αH-8α-(4-Methylpent-3-enyl)-7,9-dioxabicyclo<4.3.0>nonan-8β-yl>acetate
  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

文献信息

• FUNAKOSHI, KAZUHISA;SAKAI, KIYOSHI;HATA, TADASHI;TAMURA, CHIHIRO, TETRAHEDRON LETT., 30,(1989) N6, C. 4849-4852
  作者：FUNAKOSHI, KAZUHISA、SAKAI, KIYOSHI、HATA, TADASHI、TAMURA, CHIHIRO

  DOI：——

  日期：——