cis-3-phenyl-trans-2-oxadecalin | 138043-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: cis-3-phenyl-trans-2-oxadecalin
• 英文别名: (3R,4aR,8aS)-3-phenyl-3,4,4a,5,6,7,8,8a-octahydro-1H-isochromene
• CAS: 138043-12-6
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: COBJIHIHBXGBBT-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  trans-1-methoxymethyl-2-chloromethylcyclohexane 在 吡啶 、 magnesium 、 对甲苯磺酰氯 、 碘甲烷 作用下， 反应 2.5h， 生成 cis-3-phenyl-trans-2-oxadecalin
  参考文献：
  名称：

  Synthesis of 3-substituted trans-2-oxadecalins and 1-substituted trans-2-oxahydrindanes

  摘要：

  A study was carried out of the intramolecular cyclization of trans-1-methoxy-methyl-2-(1-hydroxyalkyl)cyclohexanes and trans-1-methoxymethyl-2-(2-hydroxy-alkyl) cyclohexanes by the action of acid chlorides of phosphorous, sulfurous and p-toluenesulfonic acids with the formation of 1-substituted trans-2-oxa-hydrindanes in low yields and 3-substituted trans-2-oxadecalins in high yields. A relationship has been established between the yields of the cyclization products and the nature of the halogenating agent. The cyclization does not proceed via an intermediate oxonium ion, but by means of an intermolecular electronic transition.

  DOI：

  10.1007/bf01172270

文献信息

• Synthesis of 3-substituted trans-2-oxadecalins and 1-substituted trans-2-oxahydrindanes
  作者：N. P. Volynskii、O. L. Alikhanova

  DOI：10.1007/bf01172270

  日期：1991.8

  A study was carried out of the intramolecular cyclization of trans-1-methoxy-methyl-2-(1-hydroxyalkyl)cyclohexanes and trans-1-methoxymethyl-2-(2-hydroxy-alkyl) cyclohexanes by the action of acid chlorides of phosphorous, sulfurous and p-toluenesulfonic acids with the formation of 1-substituted trans-2-oxa-hydrindanes in low yields and 3-substituted trans-2-oxadecalins in high yields. A relationship has been established between the yields of the cyclization products and the nature of the halogenating agent. The cyclization does not proceed via an intermediate oxonium ion, but by means of an intermolecular electronic transition.