heptacyclo[5.5.1.1.^4,10.0^2,6.0^3,11.0^5,9.0^8,12]tetradecane-13,14-dione | 89302-20-5

• 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[5.5.1.1.^4,10.0^2,6.0^3,11.0^5,9.0^8,12]tetradecane-13,14-dione
• 英文别名: Heptacyclo[6.6.0.02,6.03,13.04,11.05,9.010,14]tetradecane-7,12-dione
• CAS: 89302-20-5
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: FJFFBFBJGAESAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  heptacyclo[5.5.1.1.^4,10.0^2,6.0^3,11.0^5,9.0^8,12]tetradecane-13,14-dione 在 重氮甲烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 以81%的产率得到heptacyclo<7.7.0.0^2,6.0^3,15.0^4,12.0^5,10.0^11,16>hexadecane-7,13-dione
  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
• 作为产物：
  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

文献信息

• Photoinduced electron transfer reaction tuned by donor–acceptor pairs via the rigid, linear spacer heptacyclo[6.6.0.02,6.03,13.04,11.05,9.010,14]tetradecane
  作者：Tahsin J. Chow、Nan-Rong Chiu、Hong-Chuan Chen、Chong-Yow Chen、Wei-Shan Yu、Yi-Ming Cheng、Chung-Chih Cheng、Chen-Pin Chang、Pi-Tai Chou

  DOI：10.1016/s0040-4020(03)00881-0

  日期：2003.7

  A new class of donor-saturated hydrocarbon bridge}-acceptor (D–B–A) dyads were synthesized and utilized on a systematic approach to evaluate the corresponding photoinduced electron transfer (ET) process. Among these dyads heptacyclo[6.6.0.02,6.03,13.04,11. 05,9.010,14]tetradecane (HCTD) was used as a unique spacer, which possesses a geometry of high symmetry (D2d), rigidity and linearity. The spectroscopy

  合成了一类新的供体-饱和烃桥}-受体（D–B–A）二元组，并将其用于系统方法来评估相应的光致电子转移（ET）过程。在这些二元组中，七环[6.6.0.0 2,6 .0 3,13 .0 4,11。0 5,9 .0 10,14 ]十四烷（HCTD）被用作独特的间隔基，它具有高对称性（D 2 d），刚性和线性的几何形状。借助理论计算分析了激发态ET的光谱和动力学，作为供体/受体电子态，取向以及溶剂性质的函数。观察到供体荧光（F1波段）与宽电荷转移（CT）发射的出现相关。CT谱带的波长和强度都随溶剂极性而变化，而其上升动态与F 1谱带的衰减非常吻合。在乙腈中，CT态的衰减快于ET的速率（〜63 ps -1），因此无法解析相应的稳态发射。在苯和1,2-二硫代缩酮（3a和3b）的情况下，D和Aπ发色团以不同的方向排列，观察到了令人着迷的效果。估计的ET速率3a（3.9×10 10  s -1）明显快于3b（7×10
• Carbon-13 n.m.r. shifts for measuring transannular interaction in cage-shaped polyquinane derivatives
  作者：Tahsin J. Chow、Tung-Kung Wu、Huey-Jen Shih

  DOI：10.1039/c39890000490

  日期：——

  Transannular interactions in two systems of rigid polyquinane derivatives are detected by measuring the changes of carbon-13 chemical shifts.

  通过测量碳13化学位移的变化，可以检测到两个刚性聚奎宁衍生物的环空中相互作用。
• 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.
• ——
  作者：Simon G. Bott、Alan P. Marchand、Sulejman Alihodzic

  DOI：10.1023/a:1021845118189

  日期：——

  Crystal structures of four dibromomethylene-functionalized hexa- and heptacyclotetradecane cages are reported. 7-(Dibromomethylene)heptacyclo[6.6.0.0(2,6).0(3,13).0(4,11).0(5,9).0(10,14)] tetradecane (3): orthorhombic, Pnma, a = 14.744(1), b = 11.237(1), c = 7.4625(7) Angstrom; Z = 4; R = 0.0531 for 504 observed reflections. 7, 12-Bis(dibromomethylene)heptacyclo[6.6.0.0(2,6).0(3,13)0(4,11).0(5,9).0(10,14)]tetradecane (4): monoclinic, 12/a, a = 11.257(1), b = 9.5844(8), c = 13.884(2) Angstrom, beta = 92.254(8)degrees; Z = 4; R = 0.0413 for 663 observed reflections. 10,14-bis(dibromomethylene)hexacyclo[6.6.0.0(2,6).0(3,13).0(4,11).0(5,9)]tetradecane (6): monoclinic, P2(1)/n, a = 8.118(1), b = 15.273(4), c = 12.826(3) Angstrom, beta = 104.20(1)degrees; Z = 4; R = 0.0384 for 1392 observed reflections. 14-(dibromomethylene)hexacyclo[6.6.0.0(2,6).0(3,13).0(4,11).0(5,9)]tradecan-10-one (7): monoclinic, P2(1)/n, a = 8.2879(7), b = 15.273(1), c 10.0565(9) Angstrom, beta = 92.271(8)degrees; Z = 4; R = 0.0320 for 1402 observed reflections. The functional groups lead to slight shortening of bond lengths.
• 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