pentacyclo<5.4.0.0.^2,60.^3,100^5,9>undecane-8,11-dione | 2958-72-7

• 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: pentacyclo<5.4.0.0.^2,60.^3,100^5,9>undecane-8,11-dione
• 英文别名: pentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecane-8,11-dione；Pentacyclo<5.4.0.0^2,6.0^3,10.0^5,9>undecan-8,11-dione；pentacyclo(5.4.0.0^{2,6_.03,10_.05,9})undecane-8,11-dione；pentacyclo[5.4.0.0^2,6.0^3,10.0^5,9]undecane-8,11-dione；pentacyclo[5.4.0.02,6.03,10.05,9]undecan-8, 11-dione；pentacyclo[5.4.0.0.^2,60.^3,100^5,9]undecane-8,11-dione；(2S,3S,5R,6R,9S,10R)-pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione
• CAS: 2958-72-7
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: WTUFOKOJVXNYTJ-XWDJYJPCSA-N

物化性质

• 熔点：
  240-242 °C(lit.)
• 沸点：
  265.17°C (rough estimate)
• 密度：
  1.0844 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  pentacyclo<5.4.0.0.^2,60.^3,100^5,9>undecane-8,11-dione 在 溶剂黄146 、 锌 作用下， 反应 5.0h， 以80%的产率得到tetracyclo<6.3.0.0.^4,11,0^5,9>undecane-2,7-dione
  参考文献：
  名称：

  Butler, Douglas N.; Munshaw, Timothy J., Canadian Journal of Chemistry, 1981, vol. 59, p. 3365 - 3371

  摘要：

  DOI：
• 作为产物：
  描述：

  norbornenoquinone 以29%的产率得到pentacyclo<5.4.0.0.^2,60.^3,100^5,9>undecane-8,11-dione
  参考文献：
  名称：

  五环 [5.4.0.02,6.03,10.05,9]十一烷衍生物的 1 H 和 13 C NMR 谱的完整归属

  摘要：

  由 Diels-Alder 加合物的分子内光环加成反应衍生的化合物的产生受到了相当多的关注，但光加成产物的 NMR 光谱的分配已证明存在问题，使得结构测定变得困难。本文报告了 11, 11-二甲氧基五环 [5.4.0.02,6.03,10.O5,9] 十一烷-8-one 的质子和碳核磁共振谱的完整归属和五环 [5.4.0.02, 6.03,10.05,9] 十一烷-8,11-二酮类推。

  DOI：

  10.1002/mrc.1260310903

文献信息

• Solar driven uphill conversion of dicyclopentadiene to cyclopentadiene: an important synthon for energy systems and fine chemicals
  作者：Milan Dinda、Supratim Chakraborty、Mrinal Kanti Si、Supravat Samanta、Bishwajit Ganguly、Subarna Maiti、Pushpito K. Ghosh

  DOI：10.1039/c4ra09599e

  日期：——

  endo-dicyclopentadiene to cyclopentadiene (Cp) – which is thermodynamically uphill under ambient conditions (ΔG = +9.7 kcal mol−1; values based on computation at 273 K following CBS-QB3 methodology) – was carried out at 175–190 °C in neat state using solar energy. The reaction is thermodynamically favorable at elevated temperature. Considering heat release from the reverse reaction (ΔH = −23.4 kcal mol−1), the energy

  进行了在环境条件下（ΔG = +9.7 kcal mol -1；基于CBS-QB3方法在273 K下计算得出的值）热力学上坡的内-二环戊二烯向环戊二烯（Cp）的狄尔斯-阿尔德逆变换。在175–190°C的温度下使用太阳能在纯净状态下蒸发。该反应在升高的温度下在热力学上是有利的。考虑到逆反应释放的热量（ΔH = -23.4 kcal mol -1），能量存储效率经计算为ca。相对于集中太阳辐射中的IR分量为5.5％。通过Cp与4-苯基丁-3-yn-2-one在150–185°C的环加成反应，太阳能被进一步用于制备模型2,5-降冰片二烯衍生物（分离产率为75％）。降冰片二烯-四环烷系统已被提议用于太阳能存储，其太阳能辅助合成将有助于减少其生命周期内的碳足迹。利用太阳能合成降冰片二烯也可能对绿色化处理衍生自该化合物的燃料感兴趣。库克森的笼型酮（也已被提议作为一种能量存储介质）是由Cp和p的Die
• Thermodynamic rearrangement of the pentacyclo[5.4.0.02,6.03,10.05,9]undecane skeleton
  作者：Kata Mlinarić-Majerski、Jelena Veljković、Alan P. Marchand、Bishwajit Ganguly

  DOI：10.1016/s0040-4020(98)00680-2

  日期：1998.9

  Reaction of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (1) with ethanedithiol, when performed in the presence of a Lewis acid catalyst (F3B-OEt2), afforded the corresponding mono(ethylene dithioacetal), 2, along with 7,8-[(thioethano)thio]pentacyclo[6.3.0.02,6.03,10.05,9]undecan-11-one mono(ethylene dithioacetal) (3). Raney nickel reduction of 2 resulted in hydrogenolysis of both the dithioacetal

  在路易斯酸催化剂（F 3 B-OEt）存在下，五环[5.4.0.0 2,6 .0 3,10 .0 5,9 ]十一烷-8,11-二酮（1）与乙二硫醇的反应2），得到相应的单（亚乙基二硫缩醛）2，以及7,8-[（硫代乙醇基）硫代]五环[6.3.0.0 2,6 .0 3,10 .0 5,9 ] undecan -11-one单（亚乙基二硫缩醛）（3）。的阮内镍还原2导致二硫缩醛部分和在环丁烷环的两个氢解2并导致产物的复杂混合物的形成（7-10）。与此结果相反，阮内镍还原3可得到单一产物，即7,8-[[（硫代乙醇基）硫代]五环[6.3.0.0 2,6 .0 3,10 .0 5,9 ]十一碳烷（11），产率为35％。
• Synthesis of 8,11-dihydroxy-pentacyclo[5.4.0.02,6.03,10.05,9]Undecane-8,11-lactam
  作者：Frans J.C. Martins、Agatha M. Viljoen、Hendrik G. Kruger、Johan A. Joubert

  DOI：10.1016/s0040-4020(01)80226-x

  日期：——

  Treatment of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione with aqueous sodium cyanide produced 8,11-dihydroxy-pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-lactam. -11-Cyano-11-hydroxypentacyclo[5.4.0.02,6.03,10.05,9]-8-undecanone and 5-cyano-4-oxahexacyclo-[5.4.1.02,6.03,10.05,9.08,11]-5-dodecanol were isolated as intermediates. Structures were elucidated from extensive 1H and 13C n.m.r.

  用氰化钠水溶液处理五环[5.4.0.0 2,6 .0 3,10 .0 5,9 ]十一烷-8,11-二酮生产8,11-二羟基-五环[5.4.0.0 2,6 .0 3 ，10 .0 5,9 ]十一烷-8,11-内酰胺。-11-氰基-11-羟基五环[5.4.0.0 2,6 .0 3,10 .0 5,9 ] -8-十一烷酮和5-氰基-4-氧杂六环-[5.4.1.0 2,6 .0 3，分离出10 .0 5,9 .0 8,11 ] -5-十二烷醇作为中间体。通过广泛的1 H和13 C nmr研究阐明了结构。
• Synthesis and alkali metal picrate extraction capabilities of novel cage-functionalized 17-crown-5 and 17-crown-6 ethers
  作者：Alan P. Marchand、Kaipenchery A. Kumar、Artie S. McKim、Kata Mlinarié-Majerski、Goran Kragol

  DOI：10.1016/s0040-4020(97)00075-6

  日期：1997.3

  The syntheses of three novel cage-functionalized 17-crown-5 and 17-crown-6 ethers, i. e., 10-12, are reported and the results of alkali metal picrate extraction experiments performed by using each of these crown ethers in turn as the extractant are described. Their respective relative extraction efficiencies toward alkali metal picrates were compared with the corresponding efficiencies of 15-crown-5 and benzo-15-crown-5 solutions at the same concentration. The extraction profile of 10 (17-crown-5) toward alkali metal picrates is similar to that of 15-crown-5; however, 10 displays 33% greater avidity toward Na+ picrate. The ability of 11 (benzo-17-crown-5) to extract Li+, Rb+, and Cs+ picrates is similar to that of benzo-15-crown-5. Crown ether 10 is ca. 3 times more effective than 11 toward extraction of K+ picrate. The alkali metal picrate extraction profile of 12 (17-crown-6) resembles that of 10; however, 12 shows enhanced avidity vis-a-vis 10 toward Na+, K+, Rb+, and Cs+ picrates. (C) 1997 Elsevier Science Ltd.
• Trishomocubanes, a new class of selective and high affinity ligands for the sigma binding site
  作者：Michael Kassiou、Vu H. Nguyen、Robert Knott、MacDonald J. Christie、Trevor W. Hambley

  DOI：10.1016/0960-894x(96)00067-4

  日期：1996.3

  The synthesis, receptor binding, and preliminary structural characterisation of trishomocubanes of types pentacyclo[5.4.0.0(2,6).0(3,10).0(5,9)]undecylamines and 4-azahexacyclo[5.4.1.0(2,6).0(3,10).0(5,9)0.(8,11)] are described. These ligands demonstrated high selectivity and affinity for the sigma binding site.