(1RS,2RS,6RS,7SR)-1,6,7-trimethyltricyclo[5.2.2.0^2,6]undec-8-en-2-ol | 89398-34-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1RS,2RS,6RS,7SR)-1,6,7-trimethyltricyclo[5.2.2.0^2,6]undec-8-en-2-ol
• 英文别名: (1S,2S,6S,7R)-1,6,7-trimethyltricyclo[5.2.2.02,6]undec-8-en-2-ol
• CAS: 89398-34-5
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: NGGORWZZNTUYNK-CRWXNKLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1RS,2RS,6RS,7SR)-1,6,7-trimethyltricyclo[5.2.2.0^2,6]undec-8-en-2-ol 在 potassium hydride 作用下， 生成 (2RS,1'SR)-2-(1',4'-dimethylcyclohex-3'-enyl)-2-methylcyclopentan-1-one
  参考文献：
  名称：

  Stereoselective synthesis of (.+-.)-trichodiene

  摘要：

  DOI：

  10.1021/jo00182a038
• 作为产物：
  描述：

  (R)-3-Allyl-1,3,4-trimethyl-bicyclo[2.2.2]oct-5-en-2-one 在 吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 lithium 、 lithium bromide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 1.5h， 生成 (1RS,2RS,6RS,7SR)-1,6,7-trimethyltricyclo[5.2.2.0^2,6]undec-8-en-2-ol
  参考文献：
  名称：

  Stereoselective synthesis of (.+-.)-trichodiene

  摘要：

  DOI：

  10.1021/jo00182a038

文献信息

• ?-Cleavage of Potassium Bicyclo[2.2.2]oct-5-en-2-olates. Stereoselective synthesis of (�)-trichodiene
  作者：Roger L. Snowden、Robert Brauchli、Philippe Sonnay

  DOI：10.1002/hlca.19890720318

  日期：1989.5.3

  3-(cyclohex-3-enyl)-2-alkanones (III or IV), via β-cleavage of their potassium alkoxides in HMPA, has been investigated (cf. Table 1). As an illustration of this synthetic methodology, a stereoselective synthesis of (±)-trichodiene ((±)-1) is described which involves the β-cleavage of the tricyclic potassium alkoxides 46a and 47a to cyclopentanone 4 (cf. Scheme 7).

  的变换12双环[2.2.2]辛-5-烯-2-醇（V或VI）到3-（环己-3-烯基）-2-烷酮（III或IV），经由的β裂解其已经研究了HMPA中的醇钾盐（参见表1）。作为该合成方法的说明，描述了（±）-三茂二烯（（±）-1）的立体选择性合成，该合成涉及将三环烷氧基钾46a和47a裂解为环戊酮4（参见方案7）。
• On the mechanism of the intramolecular samarium Barbier reaction. Probes for formation of radical and organosamarium intermediates
  作者：Dennis P. Curran、Gu Xin、Wei Zhang、Paul Dowd

  DOI：10.1016/s0040-4020(97)00608-x

  日期：1997.7

  A new type of mechanistic probe for the intramolecular samarium Barbier reaction has been designed, and two different probe substrates have been investigated in detail. Remarkably, no unambiguous evidence could be obtained in favor of any of the obvious intermediates (free alkyl or alkoxy radicals, ketyls, organosamarium species) that are postulated for this reaction. Several possibilities for modified mechanisms are suggested. (C) 1997 Elsevier Science Ltd.
• Intramolecular Barbier reaction of a 3-(3′-bromopropyl) bicyclo[2.2.2]oct-5-en-2-one
  作者：Wei Zhang、Paul Dowd

  DOI：10.1016/s0040-4039(00)60354-4

  日期：1993.3

  Intramolecular Barbier reactions, initiated with lithium or magnesium metals, were carried out on a model compound 3 and afforded four products, including the cyclic product 6 and cyclopropane-containing product 7. Single and double electron transfer sequences are proposed to explain their formation.