1,1':4',1''-Tercyclohexylidene | 6051-37-2

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,1':4',1''-Tercyclohexylidene
• 英文别名: 1,4-Di(cyclohexylidene)cyclohexane；1,4-di(cyclohexylidene)cyclohexane
• CAS: 6051-37-2
• 化学式: C₁₈H₂₈
• 分子量: 244.42
• InChiKey: JTZIQWSSSQCLRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  在 lead(IV) acetate 、 硫化氢 、 calcium carbonate 、 亚磷酸三乙酯 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 2.5h， 生成 1,1':4',1''-Tercyclohexylidene
  参考文献：
  名称：

  Oligo(cyclohexylidenes): Parent Compounds and End-Functionalized Derivatives

  摘要：

  Parent oligo(cyclohexylidenes) 1(n) (n = 1-4) were synthesized using a modified Barton-Kellogg olefin synthesis. Surprisingly, the crude compounds 1(2) and 1(4) contained small amounts of the 1(n-1) and 1(n+1) homologues. As evidenced by a close examination of mass spectral data of selectively deuterated tercyclohexylidenes 1(2)d(4)d(4) and 1(2)-d(8), their formation can be attributed to scrambling of the intermediate azines. With increasing n, a marked decrease in solubility as well as an increase in thermal stability was found. Powder diffraction measurements indicate that the parent compounds 1(n), irrespective of n, pack in a similar fashion in the solid state. The theoretically (MMX, AM1, and ab initio) predicted rodlike structure of the oligo(cyclohexylidenes) was confirmed by single-crystal X-ray structures of 1(1) and three derivatives (12(1), 13(1), and 30(2)). In line with the powder diffraction data in the series 1(n), a similar packing motif was found for the derivatives. To circumvent side product formation due to azine scrambling, a different synthetic approach was used for the preparation of end-functionalized oligo(cyclohexylidenes), i.e. decarboxylation and dehydration of beta-hydroxy acids.

  DOI：

  10.1021/jo00119a014

文献信息

• Synthesis and chemistry of tetracyclo[8.2.2.22,5.26,9]-1,5,9-octadecatriene
  作者：John E. McMurry、Gregory J. Haley、James R. Matz、Jon C. Clardy、Gregory. Van Duyne、Rolf. Gleiter、Wolfgang. Schaefer、David H. White

  DOI：10.1021/ja00271a023

  日期：1986.5
• Oligo(cyclohexylidenes): Parent Compounds and End-Functionalized Derivatives
  作者：Frans J. Hoogesteger、Remco W. A. Havenith、Jan W. Zwikker、Leonardus W. Jenneskens、Huub Kooijman、Nora Veldman、Anthony L. Spek

  DOI：10.1021/jo00119a014

  日期：1995.7

  Parent oligo(cyclohexylidenes) 1(n) (n = 1-4) were synthesized using a modified Barton-Kellogg olefin synthesis. Surprisingly, the crude compounds 1(2) and 1(4) contained small amounts of the 1(n-1) and 1(n+1) homologues. As evidenced by a close examination of mass spectral data of selectively deuterated tercyclohexylidenes 1(2)d(4)d(4) and 1(2)-d(8), their formation can be attributed to scrambling of the intermediate azines. With increasing n, a marked decrease in solubility as well as an increase in thermal stability was found. Powder diffraction measurements indicate that the parent compounds 1(n), irrespective of n, pack in a similar fashion in the solid state. The theoretically (MMX, AM1, and ab initio) predicted rodlike structure of the oligo(cyclohexylidenes) was confirmed by single-crystal X-ray structures of 1(1) and three derivatives (12(1), 13(1), and 30(2)). In line with the powder diffraction data in the series 1(n), a similar packing motif was found for the derivatives. To circumvent side product formation due to azine scrambling, a different synthetic approach was used for the preparation of end-functionalized oligo(cyclohexylidenes), i.e. decarboxylation and dehydration of beta-hydroxy acids.