(+/-)-3-(Phenylmethylene)bicyclo<3.2.1>octan-8-one 8-ethylene ketal | 1026219-49-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-3-(Phenylmethylene)bicyclo<3.2.1>octan-8-one 8-ethylene ketal
• 英文别名: 3'-benzylidenespiro[1,3-dioxolane-2,8'-bicyclo[3.2.1]octane]
• CAS: 1026219-49-7
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: HLYVMIXCSNCXDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-3-(Phenylmethylene)bicyclo<3.2.1>octan-8-one 8-ethylene ketal 在 溶剂黄146 作用下， 反应 6.0h， 以38%的产率得到(+/-)-3-(Phenylmethylene)bicyclo<3.2.1>octan-8-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：

  3-Benzoylbicyclo<3.2.1>octan-8-one 在 正丁基锂 、 potassium tert-butylate 、 氧气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 叔丁醇 为溶剂， 反应 58.5h， 生成 (+/-)-3-(Phenylmethylene)bicyclo<3.2.1>octan-8-one 8-ethylene ketal
  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

文献信息

• Photoresolution of an Axially Chiral Bicyclo[3.2.1]octan-3-one: Phototriggers for a Liquid Crystal-Based Optical Switch
  作者：Yifan Zhang、Gary B. Schuster

  DOI：10.1021/jo00127a026

  日期：1995.11

  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.