hexacyclo[6.6.0.0^2,6.0^3,13.0^4,11.0^5,9]tetradecane-10,14-dione | 112533-27-4

• 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: hexacyclo[6.6.0.0^2,6.0^3,13.0^4,11.0^5,9]tetradecane-10,14-dione
• 英文别名: 4,1,3-Ethanediylidenecyclopenta(cd,gh)pentalene-6,7(1H)-dione, decahydro-；hexacyclo[6.6.0.02,6.03,13.04,11.05,9]tetradecane-10,14-dione
• CAS: 112533-27-4
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: QQZUYDRWCOEIBP-UHFFFAOYSA-N

物化性质

• 熔点：
  293.5-294.5 °C
• 沸点：
  385.5±35.0 °C(Predicted)
• 密度：
  1.462±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  6.0
• 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：

  hexacyclo[6.6.0.0^2,6.0^3,13.0^4,11.0^5,9]tetradecane-10,14-dione 在 异丙醇 作用下， 反应 0.5h， 以98%的产率得到heptacyclo[6.6.0.02,6.03,13.04,11.05,9.010,14]tetradecane-1,2-diol
  参考文献：
  名称：

  Albert, Bernhard; Elsaesser, Dominik; Heckel, Dieter, Chemische Berichte, 1991, vol. 124, # 4, p. 803 - 813

  摘要：

  DOI：
• 作为产物：
  描述：

  4-oxaheptacyclo[7.6.0.02,7.03,14.05,12.06,10.011,15]pentadecan-3-ol 在 potassium dichromate 、 硫酸 作用下， 以78%的产率得到hexacyclo[6.6.0.0^2,6.0^3,13.0^4,11.0^5,9]tetradecane-10,14-dione
  参考文献：
  名称：

  Preparation of hexacyclo[6.6.0.02,6.03,13.04,11.05,9]tetradecane-10,14-dione and derivatives

  摘要：

  DOI：

  10.1021/jo00240a036

文献信息

• Oxidative functionalization of unactivated carbon-hydrogen bonds in heptacyclo[6.6.0.02,6.03,13.04,11.05,9.010,14]tetradecane (HCTD)
  作者：Alan P. Marchand、Yanjun Wang、Sulejman Alihodzic、Derek H.R. Barton

  DOI：10.1016/s0040-4020(96)01110-6

  日期：1997.1

  Gif-type reactions have been used to perform direct oxidative functionalization of the title compound (HCTD, 1). Thus, GoAggIII and GoAggIV promoted oxidations of 1 afford 1-(2′-pyridyl)heptacyclo[6.6.0.02,6.03,13.04,11.05,9-.010,14]tetradecane [i. e., 1-(2′-pyridyl)HCTD, 2] in 6–10% isolated yield. In addition to 2, GoAggV promoted oxidation of 1 produced heptacyclo[6.6.0.02,6.03,13.04,11.05,9.010

  Gif型反应已用于进行标题化合物（HCTD，1）的直接氧化功能化。因此，GoAgg III和GoAgg IV促进了1的氧化，从而提供了1-（2'-吡啶基）七环[6.6.0.0 2,6 .0 3,13 .0 4,11 .0 5,9- .0 10,14 ]十四烷[即1-（2'-吡啶基）HCTD，2 ]，分离产率为6-10％。除2外，GoAgg V促进了1个产生的七环的氧化[6.6.0.0 2,6 .0 3,13 .0 4,11 .05,9 .0 10,14 ]十四烷-7-一（HCTD-7-one; 3）和1-（4'-吡啶基）HCTD（4），分离产率低。最后，通过使用Fe II - t- BuOOH系统进行的1氧化，得到几种产物，包括六环[6.6.0,0 2,6 .0 3,13 .0 4,11 .0 5,9 ]十四烷-10 ，14-二酮（6）和14-羟基六环[6.6.0,0 2,6 .0 3,13
• 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。
• Transannular Interactions in Polycyclic Hydrocarbons. The System of Cage-Shaped Hexacyclo[6.6.0.02,6.03,13.04,11.05,9]tetradecane Derivatives
  作者：Tahsin J. Chow、Chin-Chuan Wei、Tung-Kung Wu、Hans-Dieter Martin、Bernhard Mayer

  DOI：10.1021/jo00122a055

  日期：1995.9

  The gas phase He(I alpha) photoelectron spectra (PES) of several ketone and olefinic derivatives of the titled compound are measured. The high energy pi-orbitals (HOMO and SHOMO) of 1e show an unusually large energy splitting of 0.90 eV, while the corresponding n-orbitals of 1d appear to be nearly degenerate (<0.1 eV). The difference between these observations is analyzed with the aid of theoretical models. It is concluded in this work that the pi-pi energy splitting of 1e is derived mainly from an orbital interaction transmitted through-space (TS) across the ring. Since such a nonbonded interaction is sensitive to distance, a conformational analysis of the cycloctane ring moiety of 1e is also performed. As compared to the result of PES, it seems that the ab initio (STO-3G) method is more reliable than AM1, in which the TS interaction is somewhat underestimated.
• Chow, Tahsin J.; Wei, Chin-Chuan; Wu, Tung-Kung, Journal of the Chinese Chemical Society, 1994, vol. 41, # 6, p. 833 - 841
  作者：Chow, Tahsin J.、Wei, Chin-Chuan、Wu, Tung-Kung

  DOI：——

  日期：——
• ——
  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.