syn-Heptacyclo<10.2.1.1^5,8.0^2,6.0^2,11.0^4,9.0^7,11>hexadec-13-ene-3,10-dione | 119364-64-6

• 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: syn-Heptacyclo<10.2.1.1^5,8.0^2,6.0^2,11.0^4,9.0^7,11>hexadec-13-ene-3,10-dione
• 英文别名: syn-heptacyclo<10.2.1.1^5.8.0^2.110^4,9.0^2,6.0^7,11>hexadec-13-ene-3,10-dione；syn-heptacyclo[10.2.1.1^5.8.0^2.110^4,9.0^2,6.0^7,11]hexadec-13-ene-3,10-dione；(1R,2R,5S,6S)-heptacyclo[7.5.1.12,5.01,6.06,13.08,12.010,14]hexadec-3-ene-7,15-dione
• CAS: 119364-64-6
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: GDQSQHNNPQIJIU-VPJIYJEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  syn-Heptacyclo<10.2.1.1^5,8.0^2,6.0^2,11.0^4,9.0^7,11>hexadec-13-ene-3,10-dione 650.0 ℃ 、26.66 Pa 条件下， 以40%的产率得到syn-Pentacyclo<9.2.1.12,5.17,10.04,8>hexadeca-2(15),10(16),12-triene-3,9-dione
  参考文献：
  名称：

  Roofed polyquinanes: synthesis and electronic structure

  摘要：

  Starting from readily available norbornenobenzoquinone 7 and employing a photothermal metathesis reaction as the main strategy, novel "roofed" polyquinane bisenones 3 and 13 have been synthesized. Among these, the former is potentially serviceable for further elaboration to dodecahedrane 1. Catalytic hydrogenation of 3 provided the dione 12, which fully inscribes the circumference of dodecahedrane sphere. The "roofed" C-16-bisenone 3 has been successfully annulated to C19-bisenone 24 and C19-trisenone 26 by employing the Greene methodology and Pauson-Khand reaction, respectively. The molecular structures of 3 and 13 were computed using molecular mechanics and semiempirical MO methods. The nonbonded distances between the double bonds vary strongly with the method employed. The interactions between the pi-MO's were, therefore, probed by means of photoelectron (PE) spectroscopy. Comparison with the PE spectra of a series of model systems with increasing complexity enabled an unambiguous assignment of the observed peaks. The symmetric and antisymmetric combinations of the pi-MO's of the enone moieties of 3 and 13 show large splittings, characteristic of propano-bridged systems in which through-space and through-bond effects act in concert.

  DOI：

  10.1021/jo00025a019
• 作为产物：
  描述：

  1α,4α,10aα,5β,8β,8aα-hexahydro-1,4:5,8-dimethanoanthracene-9-10-dione 以 正己烷 为溶剂， 反应 3.0h， 以60%的产率得到syn-Heptacyclo<10.2.1.1^5,8.0^2,6.0^2,11.0^4,9.0^7,11>hexadec-13-ene-3,10-dione
  参考文献：
  名称：

  对棱烷的合成研究：1,4-双-[6] -ism烷（“ garudane”）

  摘要：

  描绘了降冰片二烯的真实的，面对面的，七环的二聚体1,4-双双六六烷6的首次合成。在初始阶段，通过三个步骤将易于获得的降冰片基对苯醌13转化为双同糖异[7] -pr二酮11，该步骤涉及立体选择性4 + 2环加成，区域和立体选择性Ti 3+还原烯二酮部分和分子内2 + 2-光环加成。多功能二酮11通过Favorskii环收缩技术和随后的官能团互变而传递了目标烃6。本文概述的新合成方法为许多新型多面体，特别是[6]-，[7]-和[ 8] -Prismanes。

  DOI：

  10.1016/s0040-4020(01)81937-2

文献信息

• MEHTA, G.;PADMA, S.;KARRA, S. R.;GOPIDAS, K. R.;CYR, D. R.;DAS, P. K.;GEO+, J. ORG. CHEM., 54,(1989) N, C. 1342-1346
  作者：MEHTA, G.、PADMA, S.、KARRA, S. R.、GOPIDAS, K. R.、CYR, D. R.、DAS, P. K.、GEO+

  DOI：——

  日期：——