9-[1-hydroxy-4-(1-phenylpiperidin-4-ylidene)cyclohexyl]-3,3-dimethyl-1,5-dioxaspiro[5.5]undecane-9-carboxylic acid | 623575-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 9-[1-hydroxy-4-(1-phenylpiperidin-4-ylidene)cyclohexyl]-3,3-dimethyl-1,5-dioxaspiro[5.5]undecane-9-carboxylic acid
• CAS: 623575-12-2
• 化学式: C₂₉H₄₁NO₅
• 分子量: 483.648
• InChiKey: HHGCTRRSHJZDTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  79.23
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  9-[1-hydroxy-4-(1-phenylpiperidin-4-ylidene)cyclohexyl]-3,3-dimethyl-1,5-dioxaspiro[5.5]undecane-9-carboxylic acid 在 盐酸 、 N,N-二甲基甲酰胺二新戊基乙缩醛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 8.0h， 生成 9-[4-Hydroxy-4'-(1-phenyl-piperidin-4-ylidene)-bicyclohexyliden-4-yl]-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecane-9-carboxylic acid
  参考文献：
  名称：

  Oligo(Cyclohexylidene)s and Oligo(Cyclohexyl)s as Bridges for Photoinduced Intramolecular Charge Separation and Recombination

  摘要：

  A series of semirigid donor-bridge-acceptor (D-B-A) molecules was synthesized to study the effect of the position and number of nonconjugated olefinic bonds in the bridge on the photoinduced charge-separation and charge-recombination kinetics. The molecules consist of a phenylpiperidine electron donor, an oligo(cyclohexylidene) or oligo(cyclohexyl) bridge, and a dicyanovinyl acceptor. Partly saturated ter(cyclohexylidene) bridges were used as well. The edge-to-edge donor-acceptor separation of the compounds under study varies between 2.89 and 15.4 Angstrom. The replacement of a C-C single bond by an olefinic bond increases the rate of charge separation with a factor of 3.0 +/- 0.8 per replaced bond. For all D-B-A compounds the extended fully charge-separated state folds to a compact charge-transfer (CCT) conformer. The rate of charge recombination (CR) of the CCT state increases with solvent polarity for those compounds having an olefinic bond located three sigma bonds from the acceptor. Thus, while in cyclohexane the CR rate is equal for all compounds, in benzene the CR rate in compounds with an olefinic bond near the acceptor is 10 times larger than in compounds with a single bond instead. It is believed that a (virtual) charge-transfer state involving the radical cation of the olefinic bond and the radical anion of the acceptor (D-B.+-A(.-)) is responsible for the enhanced CR process.

  DOI：

  10.1021/jp0271716
• 作为产物：
  描述：

  2,2-dimethylpropane-1,3-diyl bis(3,3-dimethyl-1,5-dioxaspiro[5.5]undecane-9-carboxylate) 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 4.0h， 生成 9-[1-hydroxy-4-(1-phenylpiperidin-4-ylidene)cyclohexyl]-3,3-dimethyl-1,5-dioxaspiro[5.5]undecane-9-carboxylic acid
  参考文献：
  名称：

  Oligo(Cyclohexylidene)s and Oligo(Cyclohexyl)s as Bridges for Photoinduced Intramolecular Charge Separation and Recombination

  摘要：

  A series of semirigid donor-bridge-acceptor (D-B-A) molecules was synthesized to study the effect of the position and number of nonconjugated olefinic bonds in the bridge on the photoinduced charge-separation and charge-recombination kinetics. The molecules consist of a phenylpiperidine electron donor, an oligo(cyclohexylidene) or oligo(cyclohexyl) bridge, and a dicyanovinyl acceptor. Partly saturated ter(cyclohexylidene) bridges were used as well. The edge-to-edge donor-acceptor separation of the compounds under study varies between 2.89 and 15.4 Angstrom. The replacement of a C-C single bond by an olefinic bond increases the rate of charge separation with a factor of 3.0 +/- 0.8 per replaced bond. For all D-B-A compounds the extended fully charge-separated state folds to a compact charge-transfer (CCT) conformer. The rate of charge recombination (CR) of the CCT state increases with solvent polarity for those compounds having an olefinic bond located three sigma bonds from the acceptor. Thus, while in cyclohexane the CR rate is equal for all compounds, in benzene the CR rate in compounds with an olefinic bond near the acceptor is 10 times larger than in compounds with a single bond instead. It is believed that a (virtual) charge-transfer state involving the radical cation of the olefinic bond and the radical anion of the acceptor (D-B.+-A(.-)) is responsible for the enhanced CR process.

  DOI：

  10.1021/jp0271716