(3aR*,4S*,9R*,9aS*)-3a,4,9,9a-tetrahydro-4,9-ethanonaphtho<2,3-c>furan-1,3-dione | 112136-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (3aR*,4S*,9R*,9aS*)-3a,4,9,9a-tetrahydro-4,9-ethanonaphtho<2,3-c>furan-1,3-dione
• 英文别名: endo-5,6-benzobicyclo<2.2.2>octane-2,3-dicarboxylic acid anhydride；1,2,3,4-tetrahydro-1r,4c-ethano-naphthalene-2t,3t-dicarboxylic acid-anhydride；1,2,3,4-Tetrahydro-1r,4c-aethano-naphthalin-2t,3t-dicarbonsaeure-anhydrid；(1S,8R,9R,13S)-11-oxatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-10,12-dione
• CAS: 112136-47-7
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: BTDGIUKISIULAD-IWDIQUIJSA-N

物化性质

• 沸点：
  433.8±45.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR*,4S*,9R*,9aS*)-3a,4,9,9a-tetrahydro-4,9-ethanonaphtho<2,3-c>furan-1,3-dione 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 生成 1,4-二氢-1,4-乙基桥萘
  参考文献：
  名称：

  The anodic oxidation of cis-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic acid and its derivatives: competition between oxidative bisdecarboxylation and dilactone formation

  摘要：

  DOI：

  10.1021/jo00065a023
• 作为产物：
  描述：

  1,2,3,4-tetrahydro-9-oxo-1,4-ethanonaphthalene-2,3-endo-dicarboxylic anhydride 在 盐酸 、 amalgamated zinc 作用下， 生成 (3aR*,4S*,9R*,9aS*)-3a,4,9,9a-tetrahydro-4,9-ethanonaphtho<2,3-c>furan-1,3-dione
  参考文献：
  名称：

  Takeda; Kitahonoki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 280,282

  摘要：

  DOI：

文献信息

• Metallic nickel-assisted room-temperature generation and Diels-Alder chemistry of o-xylylene intermediates
  作者：Shinichi Inaba、Richard M. Wehmeyer、Matthew W. Forkner、Reuben D. Rieke

  DOI：10.1021/jo00237a022

  日期：1988.1
• Stereospecificity and Concertedness of Retro-Diels-Alder Fragmentation in Some Diester Systems Upon Chemical Ionization
  作者：C. Denekamp、A. Weisz、A. Mandelbaum

  DOI：10.1002/(sici)1096-9888(199609)31:9<1028::aid-jms388>3.0.co;2-k

  日期：1996.9

  Retro-Diels-Alder (RDA) fragmentation of cis- and trans-2,3-diethoxycarbonyl-5,6,7,8-dibenzobicyclo[2.2.2]octanes under isobutane and methane chemical ionization conditions is highly stereospecific, giving rise to protonated diethyl maleate and fumarate, respectively. This behaviour indicates a single-step concerted mechanism, analogous to the ground-state RDA process that occurs in neutral molecules in the condensed phase. The analogous dissociation is partially stereospecific in stereoisomeric endo-, exo- and trans-2,3-diethoxycarbonylbicyclo[2.2.1]heptanes and non-stereospecific in endo-, exo- and trans-2,3-diethoxycarbonyl-5,6-benzobicyclo[2.2.2]octanes, indicating the involvement of a stepwise mechanism in the latter two systems. The different behaviour of the above systems is explained in terms of the energy of the RDA fragmentation. The differentiation and quantitative estimates of protonated diethyl maleate and fumarate were obtained from collision-induced dissociation measurements.
• Takeda; Kitahonoki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1951, vol. 71, p. 860
  作者：Takeda、Kitahonoki

  DOI：——

  日期：——
• The anodic oxidation of cis-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylic acid and its derivatives: competition between oxidative bisdecarboxylation and dilactone formation
  作者：Abid Hussain、Majid Motevalli、James H. P. Utley、Peter B. Wyatt、Yaping Gao

  DOI：10.1021/jo00065a023

  日期：1993.6
• Takeda; Kitahonoki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 280,282
  作者：Takeda、Kitahonoki

  DOI：——

  日期：——