1,2,7,9-Tetrachloro-tetracyclo<7.4.0.0^2,7.0^6,10>trideca-3,12-dien-8-one dimethyl ketal | 106881-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,7,9-Tetrachloro-tetracyclo<7.4.0.0^2,7.0^6,10>trideca-3,12-dien-8-one dimethyl ketal
• 英文别名: 1,2,7,9-tetrachloro-8,8-dimethoxytetracyclo<7.4.0.0^2,7.0^6,10>trideca-3,12-diene；1,2,7,9-Tetrachloro-8,8-dimethoxytetracyclo[7.4.0.02,7.06,10]trideca-3,12-diene
• CAS: 106881-02-1
• 化学式: C₁₅H₁₆Cl₄O₂
• 分子量: 370.103
• InChiKey: FHBXLQIWHNMATG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,7,9-Tetrachloro-tetracyclo<7.4.0.0^2,7.0^6,10>trideca-3,12-dien-8-one dimethyl ketal 在 溴 、 三正丁基氢锡 作用下， 以 四氯化碳 、 甲苯 为溶剂， 生成 9,10,12,13-Tetrachloro-pentacyclo<6.5.0.0^4,12.0^5,10.0^9,13>trideca-2,6-dien-11-one dimethyl ketal
  参考文献：
  名称：

  Synthetic studies towards prismanes: Seco-[6]-prismane

  摘要：

  The first synthesis of seco-[6]-prismane 5, the closest, one-bond-away secologue of [6]-prismane 4, from the readily available Diels-Alder adduct of 1,5-cyclooctadiene and dimethoxytetrachlorocyclopentadiene is described. The key chemical operations in the 17 step sequence are (i) 4+2-cycloaddition of singlet oxygen 20 --> 22, (ii) boron mediated fragmentation 47 --> 14 and (iii) intramolecular 2+2-photocycloaddition 14 --> 49. The methodology outlined here offers opportunities for further elaboration to [6]-prismane as well as several of its homo- and secologues.

  DOI：

  10.1016/s0040-4020(01)81936-0
• 作为产物：
  描述：

  1,10,11,12-tetrachloro-13,13-dimethoxytricyclo<8.2.1.0^2,9>-trideca-5,11-diene 在 亚甲兰 、 苯乙酮 吡啶 、 氢氧化钾 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium iodide 、 diborane(6) 作用下， 以 甲醇 、 六甲基磷酰三胺 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 230.5h， 生成 1,2,7,9-Tetrachloro-tetracyclo<7.4.0.0^2,7.0^6,10>trideca-3,12-dien-8-one dimethyl ketal
  参考文献：
  名称：

  Synthetic studies towards prismanes: Seco-[6]-prismane

  摘要：

  The first synthesis of seco-[6]-prismane 5, the closest, one-bond-away secologue of [6]-prismane 4, from the readily available Diels-Alder adduct of 1,5-cyclooctadiene and dimethoxytetrachlorocyclopentadiene is described. The key chemical operations in the 17 step sequence are (i) 4+2-cycloaddition of singlet oxygen 20 --> 22, (ii) boron mediated fragmentation 47 --> 14 and (iii) intramolecular 2+2-photocycloaddition 14 --> 49. The methodology outlined here offers opportunities for further elaboration to [6]-prismane as well as several of its homo- and secologues.

  DOI：

  10.1016/s0040-4020(01)81936-0

文献信息

• Stereochemistry of nucleophilic addition to several rigid, sterically unbiased 7-norbornanones
  作者：Haifang Li、G. Mehta、S. Padma、W. J. Le Noble

  DOI：10.1021/jo00006a010

  日期：1991.3

  A stereochemical investigation is reported of the reactions of lithium aluminum hydride (LAH) and of methyllithium with three sterically unbiased, rigid ketones: tetracyclo[7.4.0.0(2,7).0(6,10)]trideca-3,12-dien-8-one (2), pentacyclo[6.5.0.0(4,12).0(5,10).0(9,13)]tridecan-11-one (3), and pentacyclo[6.5.0.0(4,12).0(5,10).0(9,13)]trideca-2,6-dien-11-one (4). Various proton NMR techniques were brought to bear upon the dual problems of characterization and analysis of the mixtures of epimeric alcohols obtained. The results can be interpreted in terms of transition-state hyperconjugation. A comparison with literature data on other endo-substituted 7-norbornanones points up the need, in studies of electronically controlled face selection, for probes that not only have sterically equivalent faces but are also conformationally rigid.
• Accelerating effect of a remote cationic center on the Cope rearrangement. Evidence of .sigma.-participation by a norbornane C-C bond in a novel tetracyclic framework
  作者：Goverdhan Mehta、S. Padma

  DOI：10.1021/jo00255a050

  日期：1988.9
• LI, HAIFANG;MEHTA, G.;PADMA, S.;IE, NOBLE W. J., J. ORG. CHEM., 56,(1991) N, C. 2006-2011
  作者：LI, HAIFANG、MEHTA, G.、PADMA, S.、IE, NOBLE W. J.

  DOI：——

  日期：——
• MEHTA GOVERDHAN; PADMA S., J. AMER. CHEM. SOC., 109,(1987) N 7, 2212-2213
  作者：MEHTA GOVERDHAN、 PADMA S.

  DOI：——

  日期：——
• MEHTA GOVERDHAN; PADMA S.; OSAWA EIJI; BARBIRIC DORA A.; MOCHIZUKI Y., TETRAHEDRON LETT., 28,(1987) N 12, 1295-1298
  作者：MEHTA GOVERDHAN、 PADMA S.、 OSAWA EIJI、 BARBIRIC DORA A.、 MOCHIZUKI Y.

  DOI：——

  日期：——