9-cis retinylideneacetaldehyde | 107655-23-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 9-cis retinylideneacetaldehyde
• CAS: 107655-23-2
• 化学式: C₂₂H₃₀O
• 分子量: 310.48
• InChiKey: NGISIFNAHMKVQR-OVDGMIJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  9-cis retinylideneacetaldehyde 在 zinc tetraphenylporphyrin 作用下， 以 正己烷 为溶剂， 生成 beta-阿朴-14'-胡萝卜醛 、 13-cis retinylideneacetaldehyde
  参考文献：
  名称：

  视网膜同源物的三重态电位对链长的依赖性：共振拉曼光谱和三重态敏化的异构化分析

  摘要：

  DOI：

  10.1021/j100373a030
• 作为产物：
  描述：

  beta-阿朴-14'-胡萝卜醛 在 zinc tetraphenylporphyrin 作用下， 以 正己烷 为溶剂， 生成 9-cis retinylideneacetaldehyde 、 13-cis retinylideneacetaldehyde
  参考文献：
  名称：

  视网膜同源物的三重态电位对链长的依赖性：共振拉曼光谱和三重态敏化的异构化分析

  摘要：

  DOI：

  10.1021/j100373a030

文献信息

• S1- and T1-state properties of n-butylamine Schiff bases of isomeric retinylideneacetaldehyde as revealed by transient absorption and transient Raman spectroscopies and by HPLC analysis of triplet-sensitized isomerization
  作者：Yumiko Mukai、Hideki Hashimoto、Yasushi Koyama、Shoziro Kuroda、Yoshinori Hirata、Noboru Mataga

  DOI：10.1021/j100179a019

  日期：1991.12

  Transient absorption spectroscopy upon direct photoexcitation of n-butylamine Schiff base of isomeric retinylideneacetaldehyde (C22 SB) showed that each isomer generates its own S1 species showing a unique S(n) <-- S1 absorption and lifetime (all-trans, 420 ps; 9-cis, 290 ps; 11-cis, 370 ps; and 13-cis, 330 ps); no time-dependent spectral change indicating isomerization in the S1 state was seen for each isomer. Transient absorption a few nanoseconds after excitation showed that each isomer generates as a result of intersystem crossing, its own T1 species showing a unique T(n) <-- T1 absorption. Transient Raman spectroscopy upon direct photoexcitation of isomeric C22 SB showed that each isomer generates its own S1 species with a unique configuration. It showed also that the S1 state of each isomer is actually the 2(1)A(g) state, which is vibronically coupled with the S0 (1A(g)) state and gives rise to an S1, C = C stretching Raman line with an extremely high frequency (1738-1727 cm-1). The excitation profile of the particular Raman line evidenced that it is due to the S1 state probed by the transient absorption spectroscopy. Analysis by HPLC of triplet-sensitized isomerization of isomeric C22 SB showed efficient cis to trans isomerization. The quantum yields (defined as isomerization of the starting isomer per triplet species generated) were as follows: all-trans, 0.02; 9-cis, 0.5; 11-cis, 0.6; and 13-cis, 0.4. Transient Raman spectroscopy upon triplet-sensitized photoexcitation of isomeric C22 SB showed that the all-trans isomer generates its own T1 species ("all-trans" T1) and that each cis isomer generates both its own "cis" T1 and the "all-trans" T1 species. The above results indicate that no isomerization takes place in the S1 (2(1)A(g)) state, and that cis to trans isomerization takes place in the T1 state. The photophysical properties of C22 SB are compared with those of retinylideneacetaldehyde (C22 aldehyde).