3-exo-Benzoylbicyclo<3.2.1>octan-8-one 8-ethylene ketal | 70260-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-exo-Benzoylbicyclo<3.2.1>octan-8-one 8-ethylene ketal
• CAS: 70260-50-3
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: HUGWATWBOSLSBG-QKDCVEJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-exo-Benzoylbicyclo<3.2.1>octan-8-one 8-ethylene ketal 在 potassium tert-butylate 、 氧气 作用下， 以 六甲基磷酰三胺 、 叔丁醇 为溶剂， 以40%的产率得到Bicyclo<3.2.1>octan-3,8-dione 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
• 作为产物：
  描述：

  1-(1-吡咯烷)环戊烯 在 水 、 对甲苯磺酸 、 三乙胺 作用下， 生成 3-exo-Benzoylbicyclo<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

• MOMOSE TAKEFUMI; MURAOKA OSAMU; ATARASHI SHONGO; HORITA TAMIKO, CHEM. AND PHARM. BULL., 1979, 27, NO 1, 222-229
  作者：MOMOSE TAKEFUMI、 MURAOKA OSAMU、 ATARASHI SHONGO、 HORITA TAMIKO

  DOI：——

  日期：——