heptacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecane-7,12-diol | 89302-19-2

• 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: heptacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecane-7,12-diol
• 英文别名: heptacyclo[6.6.0.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14]tetradecane-7,12-diol；Heptacyclo[6.6.0.02,6.03,13.04,11.05,9.010,14]tetradecane-7,12-diol
• CAS: 89302-19-2
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: NDGUEABHBQUOME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  8.0
• 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：

  heptacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecane-7,12-diol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 以80%的产率得到heptacyclo[5.5.1.1.^4,10.0^2,6.0^3,11.0^5,9.0^8,12]tetradecane-13,14-dione
  参考文献：
  名称：

  High density polymers based on norbornadiene

  摘要：

  A novel family of cycloalkanes compounds having one or more allylidene functionalities which can be used to create cross-linked thermosets and thermoplastics having thermal stability. An example heptacyclo [6.6.0.0 2,6 .0 3,13 .0 4,11 .0 5,9 .0 10,14 ] tetradecane (HCTD) complex with terminal allylidene groups at the 7- and 12-positions (HCTD-7,12-diallylidene) was generated from norbornadiene via an efficient six-step synthesis. Thermal polymerization at temperatures ranging from 160 to 240° C. yielded a robust cross-linked material with thermal stability up to 485° C. in air, a glass transition temperature of 377° C., and a char yield (600° C.) of 56% in air. Applications include heat resistant composites utilized in the aerospace, electronic, automotive and textile industries.

  公开号：

  US11932724B1
• 作为产物：
  描述：

  7,12,-diacetoxyheptacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecane 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 17.0h， 以97%的产率得到heptacyclo<6.6.0.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14>tetradecane-7,12-diol
  参考文献：
  名称：

  Synthesis of Heptacyclo[7.7.0.0/2,6/0/3,15/0/4,12/0/5,10/0/11,16]-Hexadeca-7,13-Diene - a Novel Dimer of Barrelene Possessing Perpendobiplanar D2d Symmetry

  摘要：

  描述了七环 [7.7.0.02,6.03,15.04,12.05,10.011,16]十六碳-7,13-二烯（9）的合成过程。 二烯 (9) 的合成。二烯 (9) 是由已知的二酮分三步制得的 庚环-[6.6.0.02,6.03,13.04,11.05,9.010,14]十四烷-7,12-二酮 (5)。(5) 的双环扩展 (与重氮甲烷）的双环扩展得到了 (12)。将（12）转化成双（甲苯磺酰腙），然后进行双 Bamford -Stevens 重排，得到二烯 (9)。

  DOI：

  10.1071/ch9880817

文献信息

• Catalytic Cage Formation via Controlled Dimerization of Norbornadienes: An Entry to Functionalized HCTDs (Heptacyclo[6.6.0.0^2,6.0^3,13.0^4,11.0^5,9.0^10,14]tetradecanes)
  作者：Hee Nam Lim、Guangbin Dong

  DOI：10.1021/acs.orglett.6b00207

  日期：2016.3.4

  A general and practical catalytic method has been developed for the rapid synthesis of HCTD (heptacyclo[6.6.0.02,6.03,13.04,11.05,9.010,14]tetradecanes) and various new 7,12-disubstituted HCTDs from norbornadienes. Compared to the known approaches, this new protocol avoids stoichiometric metals, utilizes commercially available reagents as catalysts, and affords higher yields and significantly improved

  已经开发了一种通用且实用的催化方法，用于快速合成HCTD（七环[6.6.0.0 2,6 .0 3,13 .0 4,11 .0 5,9 .0 10,14 ]十四烷）和各种新的催化方法。来自降冰片二烯的7,12-二取代的HCTD。与已知方法相比，该新规程避免了化学计量的金属，利用了可商购的试剂作为催化剂，并提供了更高的收率和显着提高的选择性。此外，首次发现四环烷经历类似的内，顺，内环加成以高产率得到HCTD。HCTD的衍生化导致有效制备一系列具有生物和材料应用潜力的新型同双功能和异双功能支架。
• 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.
• Heptacyclo[5.5.1.14,10.02,6.03,11.05,9.08,12]tetradecane-13,14-dione: a novel, polycyclic perpendobiplanar D2d diketone
  作者：Alan P. Marchand、Arthur D. Earlywine

  DOI：10.1021/jo00183a037

  日期：1984.5
• MARCHAND, A. P.;EARLYWINE, A. D., J. ORG. CHEM., 1984, 49, N 9, 1660-1661
  作者：MARCHAND, A. P.、EARLYWINE, A. D.

  DOI：——

  日期：——
• BARDEN, TIMOTHY J.;PADDON-ROW, MICHAEL N., AUSTRAL. J. CHEM., 41,(1988) N 5, C. 817-822
  作者：BARDEN, TIMOTHY J.、PADDON-ROW, MICHAEL N.

  DOI：——

  日期：——