12-methyleneheptacyclo<6.6.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecan-7-one | 123105-14-6

• 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: 12-methyleneheptacyclo<6.6.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecan-7-one
• 英文别名: 12-methyleneheptacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecane-7-one；12-Methylideneheptacyclo[6.6.0.02,6.03,13.04,11.05,9.010,14]tetradecan-7-one
• CAS: 123105-14-6
• 化学式: C₁₅H₁₄O
• 分子量: 210.276
• InChiKey: NJDQTMGEQMWZKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  12-methyleneheptacyclo<6.6.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecan-7-one 在 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以38%的产率得到12-methyleneheptacyclo<6.6.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecan-7-one
  参考文献：
  名称：

  通过钠促进的 12-亚甲基七环-[6.6.02,6.03,13.04,11.05,9.010,14]十四烷-7-one 的还原二聚反应形成频哪醇的结构

  摘要：

  由钠促进亚甲基七环-[6.6.02,6.03,13.04,11.05,9.010,14]十四酮的还原偶联产生的频哪醇具有一种构象，其中频哪醇碳上的等价基团实际上彼此垂直。这种旋转使空间相互作用最小化，因此分子中所有片段的几何形状都在预期值内。

  DOI：

  10.1007/bf01665280
• 作为产物：
  描述：

  12-Hydroxy-12-methylheptacyclo[6.6.0.02,6.03,13.04,11.05,9.010,14]tetradecan-7-one 在 吡啶 、 三氯氧磷 作用下， 以87%的产率得到12-methyleneheptacyclo<6.6.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecan-7-one
  参考文献：
  名称：

  Syntheses of Rigid and Semirigid Molecules for Investigations of Photoinduced Electron Transfer Reactions

  摘要：

  Investigations of electron transfer reactions in donor-spacer-acceptor (DSA) molecules posessing small numbers of reactive conformations have significantly increased understanding of factors that control transfer rate constants. The syntheses of polynorbornane-based DSA molecules 12, 16, 20, 26, 30, and 34 and heptacyclotetradecane-based DSA molecules 40, 47, 51, and 60 are described. These molecules have been used to explore the effects of electronic symmetry, solvent electronic structure, and temperature on photoinduced electron transfer reactions.

  DOI：

  10.1021/jo00118a023

文献信息

• Albert, Bernhard; Elsaesser, Dominik; Martin, Hans-Dieter, Chemische Berichte, 1991, vol. 124, # 12, p. 2871 - 2878
  作者：Albert, Bernhard、Elsaesser, Dominik、Martin, Hans-Dieter、Mayer, Bernhard、Chow, Tahsin J.、et al.

  DOI：——

  日期：——
• Syntheses of Rigid and Semirigid Molecules for Investigations of Photoinduced Electron Transfer Reactions
  作者：Krishna Kumar、Ronald J. Tepper、Yang Zeng、Matthew B. Zimmt

  DOI：10.1021/jo00118a023

  日期：1995.6

  Investigations of electron transfer reactions in donor-spacer-acceptor (DSA) molecules posessing small numbers of reactive conformations have significantly increased understanding of factors that control transfer rate constants. The syntheses of polynorbornane-based DSA molecules 12, 16, 20, 26, 30, and 34 and heptacyclotetradecane-based DSA molecules 40, 47, 51, and 60 are described. These molecules have been used to explore the effects of electronic symmetry, solvent electronic structure, and temperature on photoinduced electron transfer reactions.
• Structure of the pinacol formed via sodium-promoted reductive dimerization of 12-methyleneheptacyclo-[6.6.02,6.03,13.04,11.05,9.010,14]tetradecan-7-one
  作者：Simon G. Bott、Alan P. Marchand、Zenghui Liu

  DOI：10.1007/bf01665280

  日期：1995.7

  The pinacol resulting from sodium promoted reductive coupling of a methyleneheptacyclo-[6.6.02,6.03,13.04,11.05,9.010,14]tetradecanone possesses a conformation in which equivalent groups on the pinacol carbon are virtually perpendicular to each other. This rotation minimizes steric interactions, thus the geometries of all the fragments in the molecule are within expected values.

  由钠促进亚甲基七环-[6.6.02,6.03,13.04,11.05,9.010,14]十四酮的还原偶联产生的频哪醇具有一种构象，其中频哪醇碳上的等价基团实际上彼此垂直。这种旋转使空间相互作用最小化，因此分子中所有片段的几何形状都在预期值内。