(-)-3-endo-8-(Phenylmethylene)bicyclo<3.2.1>octan-3-ol | 172367-06-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-3-endo-8-(Phenylmethylene)bicyclo<3.2.1>octan-3-ol
• 英文别名: (+/-)-3-endo-8-(Phenylmethylene)bicyclo<3.2.1>octan-3-ol
• CAS: 172367-06-5；172367-08-7
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: QMGFLMFIRNOKME-DCBMWLRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (-)-3-endo-8-(Phenylmethylene)bicyclo<3.2.1>octan-3-ol 在 吡啶 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以76%的产率得到(-)-3-endo-8-(Phenylmethylene)bicyclo<3.2.1>octan-3-one
  参考文献：
  名称：

  Photoresolution of an Axially Chiral Bicyclo[3.2.1]octan-3-one: Phototriggers for a Liquid Crystal-Based Optical Switch

  摘要：

  The axially chiral ketones 8-(phenylmethylene)bicyclo[3.2.1]octan-3-one (1) and 3-(phenylmethylene)bicyclo[3.2,1]octan-8-one (2) were prepared and investigated for suitability as a chiroptical trigger in a liquid crystal-based optical switch. Irradiation of optically active ketone 1 with unpolarized light leads to its efficient photoracemization. Its irradiation with circularly polarized light leads to partial photoresolution with an enantiomeric excess sufficient for it to function as a chiroptical trigger. However, 1 is not sufficiently soluble in ZLI-1167, a nematic liquid crystalline material, to induce a measurable pitch. Ketone 2 is unstable to irradiation and is not suitable for use as a chiroptical trigger.

  DOI：

  10.1021/jo00127a026
• 作为产物：
  描述：

  benzylphosphonic dichloride 在 四丁基氟化铵 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 36.5h， 生成 (-)-3-endo-8-(Phenylmethylene)bicyclo<3.2.1>octan-3-ol
  参考文献：
  名称：

  Photoresolution of an Axially Chiral Bicyclo[3.2.1]octan-3-one: Phototriggers for a Liquid Crystal-Based Optical Switch

  摘要：

  The axially chiral ketones 8-(phenylmethylene)bicyclo[3.2.1]octan-3-one (1) and 3-(phenylmethylene)bicyclo[3.2,1]octan-8-one (2) were prepared and investigated for suitability as a chiroptical trigger in a liquid crystal-based optical switch. Irradiation of optically active ketone 1 with unpolarized light leads to its efficient photoracemization. Its irradiation with circularly polarized light leads to partial photoresolution with an enantiomeric excess sufficient for it to function as a chiroptical trigger. However, 1 is not sufficiently soluble in ZLI-1167, a nematic liquid crystalline material, to induce a measurable pitch. Ketone 2 is unstable to irradiation and is not suitable for use as a chiroptical trigger.

  DOI：

  10.1021/jo00127a026