2-(all-trans-retinylidene)indan-1,3-dione

• 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: 2-(all-trans-retinylidene)indan-1,3-dione
• 英文别名: 2-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenylidene]indene-1,3-dione
• 化学式: C₂₉H₃₂O₂
• 分子量: 412.572
• InChiKey: JYABEAZOVFCBOD-UZLKZSPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3-茚满二酮 、 视黄醛 以 甲醇 为溶剂， 生成 2-(all-trans-retinylidene)indan-1,3-dione
  参考文献：
  名称：

  Femtosecond Transient Absorption Spectroscopic Study of a Carbonyl-Containing Carotenoid Analogue, 2-(all-trans-Retinylidene)-indan-1,3-dione

  摘要：

  The photophysical properties of a carbonyl-containing carotenoid analogue in an s-cis configuration, relative to the conjugated pi system, 2-(all-trans-retinylidene)-indan-1,3-dione (C20Ind), were investigated by femtosecond time-resolved spectroscopy in various solvents. The lifetime of the optically forbidden S-1 state of C20Ind becomes long as solvent polarity increases. This trend is completely opposite to the situation of S1-ICT dynamics of carbonyl containing carotenoids, such as peridinin and fucoxanthin. Excitation energy dependence of the transient absorption measurements shows that the transient absorption spectra in nonpolar solvents were originated from two distinct transient species, while those in polar and protic solvents are due to a single transient species. By referring to the results of MNDO-PSDCI (modified neglect of differential overlap with partial single- and double configuration interaction) calculations, we conclude: (1) in polar and protic solvents, the S-1 state is generated following excitation up to the S-2 state; (2) in nonpolar solvents, however, both the S-1 and the (1)n pi* states are generated; and (3) C20Ind does not generate the S1-ICT state, despite the fact that it has two conjugated carbonyl groups.

  DOI：

  10.1021/jp111313f

文献信息

• Potential prophylactic antitumor activity of retinylidene 1,3-diketones
  作者：Nancy Acton、Arnold Brossi、Dianne L. Newton、Michael B. Sporn

  DOI：10.1021/jm00181a019

  日期：1980.7

  Treatment of all-trans-retinal with a series of 1,3-diketones using Knoevenagel conditions gave the expected condensation products. These retinylidene 1,3-diketones were characterized and their biological activities in the hamster tracheal organ culture test measured. It was found that the cyclohexane- 1,3-dione derivatives are highly active in this in vitro assay, while other 1,3-diketones are less active. Retinylidenedimedone has been chosen for further evaluation.
• Femtosecond Transient Absorption Spectroscopic Study of a Carbonyl-Containing Carotenoid Analogue, 2-(all-<i>trans</i>-Retinylidene)-indan-1,3-dione
  作者：Toshiyuki Kusumoto、Daisuke Kosumi、Chiasa Uragami、Harry A. Frank、Robert R. Birge、Richard J. Cogdell、Hideki Hashimoto

  DOI：10.1021/jp111313f

  日期：2011.3.24

  The photophysical properties of a carbonyl-containing carotenoid analogue in an s-cis configuration, relative to the conjugated pi system, 2-(all-trans-retinylidene)-indan-1,3-dione (C20Ind), were investigated by femtosecond time-resolved spectroscopy in various solvents. The lifetime of the optically forbidden S-1 state of C20Ind becomes long as solvent polarity increases. This trend is completely opposite to the situation of S1-ICT dynamics of carbonyl containing carotenoids, such as peridinin and fucoxanthin. Excitation energy dependence of the transient absorption measurements shows that the transient absorption spectra in nonpolar solvents were originated from two distinct transient species, while those in polar and protic solvents are due to a single transient species. By referring to the results of MNDO-PSDCI (modified neglect of differential overlap with partial single- and double configuration interaction) calculations, we conclude: (1) in polar and protic solvents, the S-1 state is generated following excitation up to the S-2 state; (2) in nonpolar solvents, however, both the S-1 and the (1)n pi* states are generated; and (3) C20Ind does not generate the S1-ICT state, despite the fact that it has two conjugated carbonyl groups.