1,4-Methano-1,4-dihydro-9,10-anthraquinone | 32745-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-Methano-1,4-dihydro-9,10-anthraquinone
• 英文别名: 1,4-dihydro-1,4-methano-9,10-anthraquinone；(1S,12R)-tetracyclo[10.2.1.02,11.04,9]pentadeca-2(11),4,6,8,13-pentaene-3,10-dione
• CAS: 32745-55-4
• 化学式: C₁₅H₁₀O₂
• 分子量: 222.243
• InChiKey: UGTIHRDRMFXRLO-DTORHVGOSA-N

物化性质

• 熔点：
  156 °C
• 沸点：
  409.0±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  1,4-Methano-1,4-dihydro-9,10-anthraquinone 在 palladium on activated charcoal 氢气 、 双氧水 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 (1R,10S,11R,14S)-15-oxapentacyclo[8.4.1.111,14.01,10.03,8]hexadeca-3,5,7-triene-2,9-dione
  参考文献：
  名称：

  Electronic control of stereoselectivity. 6. Directionality of singlet oxygen addition to 1,4-dimethoxynaphthalenes laterally fused to bridged bicyclic systems

  摘要：

  DOI：

  10.1021/jo01312a019
• 作为产物：
  描述：

  (S)-2-p-tolylsulfinyl-1,4-naphthoquinone 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 1,4-Methano-1,4-dihydro-9,10-anthraquinone
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones

  摘要：

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.

  DOI：

  10.1021/jo00051a036

文献信息

• Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis
  作者：Sambasivarao Kotha、Rama Gunta

  DOI：10.3762/bjoc.12.177

  日期：——

  Here, we report a simple synthetic strategy to the bridgehead vicinal diallylation of norbornene derivatives. These substrates are useful to generate propellanes via ring-closing metathesis. Single-crystal X-ray diffraction analysis of four compounds led to the realization of configurational correction of earlier reported molecules.

  在这里，我们报告了降冰片烯衍生物桥头邻位二甲苯基化的简单合成策略。这些底物可用于通过闭环复分解反应生成丙炔。四种化合物的单晶X射线衍射分析导致了较早报道的分子的构型校正。
• Experimental and theoretical investigations into the stereoselectivities of peracid promoted epoxidations of substituted norbornenes and norbornadienes
  作者：Alan P Marchand、Bishwajit Ganguly、Rajesh Shukla、Kasireddy Krishnudu、V Satish Kumar、William H Watson、Satish G Bodige

  DOI：10.1016/s0040-4020(99)00464-0

  日期：1999.7

  MCPBA promoted diastereoselective epoxidations of functionalized norbornenes and norbornadienes have been performed, The experimental results thereby obtained have been evaluated by using semiempirical (AMI) quantum chemical modeling. The AMI computational results are consistent with experiment and correctly predict the major product of all MCPBA promoted epoxidations studied herein. Product characterization was assisted via the results of X-ray crystallographic structural analysis in the case of 10a and by comparison of calculated vs. experimental C-13 NMR chemical shifts of the cyclopropyl carbon atoms in 12a and 12b. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Photocyclization of norbornadienes fused with quinone units
  作者：Takanori Suzuki、Yoshiro Yamashita、Toshio Mukai、Tsutomu Miyashi

  DOI：10.1016/s0040-4039(00)80309-3

  日期：1988.1
• Asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones
  作者：M. Carmen Carreno、Jose L. Garcia Ruano、Antonio Urbano

  DOI：10.1021/jo00051a036

  日期：1992.12

  The asymmetric Diels-Alder reactions of (S)-2-(p-tolylsulfinyl)-1,4-naphthoquinones 1a-c with cyclic dienes have been explored. The high pi facial diastereoselectivity observed can be reversed in the presence of ZnBr2. Evidence is presented to show that the regiochemical outcome of these reactions is controlled only by the sulfinyl group. The in situ cycloaddition/pyrolytic sulfoxide elimination starting from chiral 1a-c offers a convenient new route for the construction of enantiomerically pure 1,4-dihydro-9,10-anthraquinones (+)-10 and (+)-12a-c.
• Electronic control of stereoselectivity. 6. Directionality of singlet oxygen addition to 1,4-dimethoxynaphthalenes laterally fused to bridged bicyclic systems
  作者：Leo A. Paquette、Francois Bellamy、Michael C. Boehm、Rolf Gleiter

  DOI：10.1021/jo01312a019

  日期：1980.11