Hexacyclo<9.5.0.0^1,3.0^2,10.0^3,9.0^9,11>hexadecane-2,10-dimethanol | 154989-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Hexacyclo<9.5.0.0^1,3.0^2,10.0^3,9.0^9,11>hexadecane-2,10-dimethanol
• 英文别名: [9-(Hydroxymethyl)-1-hexacyclo[7.7.0.02,8.02,16.08,10.010,16]hexadecanyl]methanol
• CAS: 154989-00-1
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: ALBIXRMREKXBEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Hexacyclo<9.5.0.0^1,3.0^2,10.0^3,9.0^9,11>hexadecane-2,10-dimethanol 以 乙醚 为溶剂， 反应 1.0h， 以58%的产率得到15,16-Bis(hydroxymethyl)tetracyclo<7.5.2.0.0^2,8>hexadeca-2(8),15-diene
  参考文献：
  名称：

  Molecular Structures and Photochemical Behavior of Doubly Bridged Prismanes

  摘要：

  The molecular structures of four prismanes were determined by X-ray analysis. The diester derivatives 1a, 1b, and 3 show a lengthening of the vicinal bonds and a shortening of the distal bonds in the cyclopropane moieties, whereas in bis(hydroxymethyl) compound 2 no significant bond length differences were found. These structural properties affect their chemical behavior: if prismanes la and Tb are irradiated with UV light a selective cleavage of the elongated cyclopropane bonds affords exclusively Dewar benzenes 4a and 4b as primary products whereas from 2 both possible isomeric Dewar benzenes 8 and 9 are obtained.

  DOI：

  10.1021/jo00089a024
• 作为产物：
  描述：

  1,8-环十四二炔 在 正丁基锂 、 三氯化铝 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 5.5h， 生成 Hexacyclo<9.5.0.0^1,3.0^2,10.0^3,9.0^9,11>hexadecane-2,10-dimethanol
  参考文献：
  名称：

  Synthesis of doubly bridged prismanes: an investigation of the photochemical behavior of doubly bridged Dewar benzenes

  摘要：

  Starting from cyclic acetylenes, two stereoisomeric doubly bridged Dewar benzenes of type 14 and 15 were synthesized, and the effects of the chain length and the nature of two other functional groups on their photochemical behavior were examined. The isomers with bridges spanning the 1,4- and 2,3-positions, 14b,c and 25b, reacted to form the respective prismanes, 17b,c and 27b. Isomers 15b-d, with bridges spanning the 1,2- and 3,4-positions, revealed a more complex photochemistry. through consecutive transposition reactions via a total of five intermediates, an unexpected phthalic/terephthalic ester rearrangement was observed. Prismane 38b and Dewar benzenes 39b,c could be characterized directly, and the existence of the other intermediates was deduced indirectly.

  DOI：

  10.1021/jo00079a019

文献信息

• Synthesis of doubly bridged prismanes: an investigation of the photochemical behavior of doubly bridged Dewar benzenes
  作者：Rolf Gleiter、Bjoern Treptow

  DOI：10.1021/jo00079a019

  日期：1993.12

  Starting from cyclic acetylenes, two stereoisomeric doubly bridged Dewar benzenes of type 14 and 15 were synthesized, and the effects of the chain length and the nature of two other functional groups on their photochemical behavior were examined. The isomers with bridges spanning the 1,4- and 2,3-positions, 14b,c and 25b, reacted to form the respective prismanes, 17b,c and 27b. Isomers 15b-d, with bridges spanning the 1,2- and 3,4-positions, revealed a more complex photochemistry. through consecutive transposition reactions via a total of five intermediates, an unexpected phthalic/terephthalic ester rearrangement was observed. Prismane 38b and Dewar benzenes 39b,c could be characterized directly, and the existence of the other intermediates was deduced indirectly.
• Molecular Structures and Photochemical Behavior of Doubly Bridged Prismanes
  作者：Rolf Gleiter、Bjoern Treptow、Hermann Irngartinger、Thomas Oeser

  DOI：10.1021/jo00089a024

  日期：1994.5

  The molecular structures of four prismanes were determined by X-ray analysis. The diester derivatives 1a, 1b, and 3 show a lengthening of the vicinal bonds and a shortening of the distal bonds in the cyclopropane moieties, whereas in bis(hydroxymethyl) compound 2 no significant bond length differences were found. These structural properties affect their chemical behavior: if prismanes la and Tb are irradiated with UV light a selective cleavage of the elongated cyclopropane bonds affords exclusively Dewar benzenes 4a and 4b as primary products whereas from 2 both possible isomeric Dewar benzenes 8 and 9 are obtained.