(1S,2S,6R,7R,10R)-4-Oxa-tricyclo[5.2.1.02,6]decan-10-ol | 122601-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1S,2S,6R,7R,10R)-4-Oxa-tricyclo[5.2.1.02,6]decan-10-ol
• CAS: 122601-65-4
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: SMTRQOLYIYPGQN-WCNIORAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  4-oxatricyclo[5.2.1.0^2,6]dec-8-en-10-one 在 sodium tetrahydroborate 、 二氮烯 作用下， 反应 2.0h， 生成 (1S,2S,6R,7R,10R)-4-Oxa-tricyclo[5.2.1.02,6]decan-10-ol
  参考文献：
  名称：

  Absence of Heteroatom Kinetic Effects in p-Route to Carbocations

  摘要：

  DOI：

  10.3987/com-88-s100

文献信息

• π-Facial selectivities in nucleophilic additions to 4-hetero-tricyclo[5.2.1.02,6]decan-10-ones and 4-hetero-tricyclo[5.2.1.02,6]dec-8-en-10-ones: an experimental and computational study
  作者：Goverdhan Mehta、Vanessa Gagliardini、U.Deva Priyakumar、G.Narahari Sastry

  DOI：10.1016/s0040-4039(02)00320-9

  日期：2002.4

  Several endo-tricyclo[5.2.1.02,6]decan-10-ones and endo-tricyclo[5.2.1.02,6]dec-8-en-10-ones with hetero atom modifications at the distal C-4 position have been subjected to hydride reduction. π-Face selectivities in these systems are largely governed by the same electronic factors that were earlier identified in the case of the norbornyl system. A computational study demonstrates good predictability

  在远端C-4位置具有杂原子修饰的几个内-三环[5.2.1.0 2,6 ] decan-10- one和内-三环[5.2.1.0 2,6 ] dec-8-en-10-one具有进行氢化物还原。这些系统中的π-表面选择性在很大程度上受先前在降冰片烯系统中所确定的相同电子因素的支配。一项计算研究表明，在半经验水平上具有良好的可预测性。
• 4-Oxatricyclo[5.2.1.0^2,6]decan-10-one and 4-Oxatricyclo[5.2.1.0^2,6]dec-8-en-10-one. Experimental and DFT Investigations of the π-Selectivities
  作者：Veejendra K. Yadav、Rengarajan Balamurugan

  DOI：10.1021/jo015945t

  日期：2002.1.1

  Ab initio MO and experimental pi-selectivities of hydride additions to 4-oxatricyclo[5.2.1.0(2.6)]decan-10-one and 4-oxatricyclo[5.2.1.0(2.6)]dec-8-en-10-one are described. The interactions Of sigma(C1-C2) and sigma(C6-C7) with pi*(C=O), on one hand, and those of sigma(C1-C9) and sigma(C7-C8) with pi*(C=O), on the other hand, support anti-selectivities for both. This is in full accordance with the experiments. The arguments that are based on electrostatic interactions and electron donation from the ring oxygen do not apply.