heptacyclo<7.6.1.0^2,8.0^3,7.0^4,13.0^6,12.0^10,15>hexadecane-11,14-dione | 110745-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptacyclo<7.6.1.0^2,8.0^3,7.0^4,13.0^6,12.0^10,15>hexadecane-11,14-dione
• 英文别名: heptacyclo<7.6.1.0^2,8.0^3,7.0^4.13.0^6,12.0^10,15>hexadeca-11,14-dione；heptacyclo<7.6.1.0^2,8.0^3,7.0^6,12.0^10,15>hexadecane-11,14-dione；1,4-bishomo-6-seco[7]prismane-15,16-dione；heptacyclo[7.6.1.02,8.03,7.04,13.06,12.010,15]hexadecane-11,14-dione
• CAS: 110745-86-3
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: DVPGKJCZTGZWQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  heptacyclo<7.6.1.0^2,8.0^3,7.0^4,13.0^6,12.0^10,15>hexadecane-11,14-dione 在 吡啶 、 六甲基磷酰三胺 、 sodium tetrahydroborate 、 sodium iodide 作用下， 以 甲醇 为溶剂， 反应 11.25h， 生成 11,14-diiodoheptacyclo<7.6.1.0^2,8.0^3,7.0^4.13.0^6,12.0^10,15>hexadecane
  参考文献：
  名称：

  Synthetic studies towards prismanes: Exploratory efforts en route to [7]-prismane homo- and secologues

  摘要：

  Novel heptacyclic triones 8 and 9 have been synthesised. A series of probing experiments on the heptacyclic ketones 3, 8 and 9, in quest for [7]-prismane homo- and secologues are described. Synthesis of novel polyhedranes 23-25 through thermal 2 + 2-cycloreversion of 3, 8 and 17, respectively, has been achieved. Our results point to the need for devising de novo strategy for the creation of higher prismanic frameworks.

  DOI：

  10.1016/s0040-4020(01)81938-4
• 作为产物：
  描述：

  1α,4α,4aβ,10aβ,5α,8α,8aβ,9aβ-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione 以 丙酮 、 苯 为溶剂， 反应 4.0h， 以60%的产率得到heptacyclo<7.6.1.0^2,8.0^3,7.0^4,13.0^6,12.0^10,15>hexadecane-11,14-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

• D2h-bishomohexaprismane ("garudane"). Design of the face-to-face 2 + 2 dimer of norbornadiene
  作者：Goverdhan Mehta、S. Padma

  DOI：10.1021/ja00257a076

  日期：1987.11

  Synthese a partir de la reaction de Diels Alder entre la benzoquinone-1,4 et le cyclopentadiene-1,3

  Synthese a partir de la reaction de Diels Alder entre la benzoquinone-1,4 et le cyclopentadiene-1,3
• Synthesis and characterization of a novel pentacyclic C16 diketone and derivatives
  作者：Simon G. Bott、Alan P. Marchand、Duddu Raja Gopal

  DOI：10.1007/bf01195731

  日期：1993.11

  The syntheses and crystal structures of pentacyclo[9.4. 1.0(5,14).0(7,13).0(12.15)]hexadecane-3,9-dione (2), a novel C-16 diketone with potential inclusion ability, and the products of the reaction of 2 with n-butyllithium and meso-erythritol (i.e., meso-1,2,3,4-butanetetrol) are described. Crystal data: 2.H2O, orthorhombic, Pmmn, a = 10.7385(8), b = 9.0188(6), c = 6.8411(4) angstrom, V = 662.55(7) angstrom3, and R = 0.039 (379 reflections); 3 (product from reaction with n-butyllithium), triclinic, P1BAR, a = 8.7192(7), b = 10.9351(8), c = 12.1842(8) angstrom, alpha = 68.933(5), beta = 75.850(6), gamma = 80.309(6)-degrees, V = 1047.0(1) angstrom3, and R = 0.081 (1811 reflections); 4 (product from reaction with erythritol), triclinic, P1BAR, a = 7.7224(8), b = 10. 1976(8), c = 10.7021(9) angstrom, alpha = 85.405(7), beta = 85.766(8), gamma = 76.056(7)-degrees, V = 814.0(1) angstrom3 , and R = 0.052 (1471 reflections).
• MEHTA, GOVERDHAN;PADMA, S., J. AMER. CHEM. SOC., 109,(1987) N 23, 7230-7232
  作者：MEHTA, GOVERDHAN、PADMA, S.

  DOI：——

  日期：——
• (S<i>S</i>)-2-(<i>p</i>-Tolylsulfinyl)norborneno-<i>p</i>-benzoquinones:  A New Type of Facially Perturbed Enantiopure Quinones
  作者：M. Carmen Carreño、José L. García Ruano、Antonio Urbano、M. Isabel López-Solera

  DOI：10.1021/jo9618942

  日期：1997.2.1

  The syntheses and asymmetric Diels-Alder reactions of (SS)-2-(p-tolylsulfinyl)norboreno-p-benzoquinones 10 and 11 with cyclopentadiene are reported. The cycloadditions allowed the highly stereoselective obtention of the four possible endo adducts 12-15, optically pure synthetic equivalents of norborneno-p-benzoquinone-cyclopentadiene bisadducts. The detailed study of the H-1-NMR spectra of the adducts pointed out the anisotropic effects exerted by the sulfinyl moiety on the spectroscopic behavior of these rigid systems. In all cases, the pi-facial selectivities were fully controlled by the sulfinyl group being possible to reverse the diastereoselection in thermal conditions and in the presence of ZnBr2. The stereoselective synthesis of the cage compound 5, precursor of garudane, was achieved from cycloadduct endo-syn-13.
• Observation of a transannular Cannizzaro reaction in a caged [7]prismane related system
  作者：Goverdhan Mehta、S. Padma

  DOI：10.1021/jo00003a068

  日期：1991.2