trans-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid (11,12)-diethyl ester | 83742-19-2

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: trans-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid (11,12)-diethyl ester
• 英文别名: diethyl 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate；trans-7,8-diethoxycarbonyl-2,3,5,6-dibenzo<2.2.2>bicyclooctane；trans-11,12-diethoxycarbonyl-9,10-dihydro-9,10-ethanoanthracene；(+/-)-trans-9,10-dihydro-9,10-ethano-anthracene-dicarboxylic acid-(11.12)-diethyl ester；(+/-)-trans-9,10-Dihydro-9,10-aethano-anthracen-dicarbonsaeure-(11.12)-diaethylester
• CAS: 83742-19-2；93368-53-7
• 化学式: C₂₂H₂₂O₄
• 分子量: 350.414
• InChiKey: KVAFCEQAGCSSBJ-YRPNKDGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trans-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid (11,12)-diethyl ester 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 trans-(11S,12S)-(-)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid
  参考文献：
  名称：

  Synthesis and antiproliferative action of a novel series of maprotiline analogues

  摘要：

  The synthesis of a diverse library of compounds structurally related to maprotiline, a norepinephrine reuptake transporter (NET) selective antidepressant which has recently been identified as a novel in vitro antiproliferative agent against Burkitt's lymphoma (BL) cell lines is reported. A series of 9,10-dihydro-9,10-ethanoanthracenes were synthesised with modifications to the bridge of the dihydroethanoanthracene structure and with alterations to the basic side chain. A number of compounds were found to reduce cell viability to a greater extent than maprotiline in BL cell lines. In addition a related series of novel 9-substituted anthracene compounds were investigated as intermediates in the synthesis of 9,10-dihydro-9,10-ethanoanthracenes. These compounds proved the most active from the screen and were found to exert a potent caspase-dependant apoptotic effect in the BL cell lines, while having minimal effect on the viability of peripheral blood mononuclear cells (PBMCs). Compounds also displayed activity in multi-drug resistant (MDR) cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.076
• 作为产物：
  描述：

  Anthracene-maleic anhydride diels-alder adduct 在 硫酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 trans-9,10-dihydro-9,10-ethano-anthracene-11,12-dicarboxylic acid (11,12)-diethyl ester
  参考文献：
  名称：

  Stereospecificity and Concertedness of Retro-Diels-Alder Fragmentation in Some Diester Systems Upon Chemical Ionization

  摘要：

  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.

  DOI：

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

文献信息

• Selectivity for the methoxycarbonylation of ethylene versus COethylene copolymerization with catalysts based on C4-bridged bidentate phosphines and phospholes
  作者：Simon Doherty、Edward G Robins、Julian G Knight、Colin R Newman、Barrie Rhodes、Paul A Champkin、William Clegg

  DOI：10.1016/s0022-328x(01)01180-9

  日期：2001.12

  and diphosphines 11,12-bis(diphenylphosphinomethyl)-9,10-dihydro-9,10-ethano-anthracene (cis, 5a; trans, 5b) and their corresponding palladium complexes [(PP)PdCl2] (6a–d) have been prepared and characterized. Single-crystal X-ray analyses of 6a–d have been undertaken and they reveal that 4a and b and 5a and b coordinate in a bidentate manner forming seven-membered chelate rings with natural bite

  C 4桥基磷酸11,12-双（2,3,4,5-四甲基磷酰基甲基）-9,10-二氢-9,10-乙基蒽（顺式，4a ;反式，4b）和二膦11,12制备了双（二苯基膦基甲基）-9,10-二氢-9,10-乙基蒽（顺式，5a；反式，5b）及其相应的钯配合物[（PP）PdCl 2 ]（6a – d）和特点。已经对6a – d进行了单晶X射线分析，结果表明4a和b和图5a和b在二齿方式形成具有98.62和100.30°之间自然咬合角7元螯合环坐标。已经使用4a和b以及5a和b研究了钯催化的乙烯的羰基化。由4a和b，乙酸钯和甲磺酸产生的催化剂混合物对于乙烯与一氧化碳的共聚具有选择性，从而产生低分子量聚合物。令人惊讶的是，基于顺式-（4a）的催化剂体系的活性明显高于基于其反式异构体的催化剂，4b。用[1,4-双（2,3,4,5-四甲基膦酰基）丁烷} Pd（OAc）2 ]进行的比较催化剂测试突出显示了四碳
• Garrigues, Bernard; Laporte, Christian; Laurent, Regis, Liebigs Annalen, 1996, # 5, p. 739 - 741
  作者：Garrigues, Bernard、Laporte, Christian、Laurent, Regis、Laporterie, Andre、Dubac, Jacques

  DOI：——

  日期：——
• The cis and trans 12-Benzoyl-9,10-dihydro-9,10-ethanoanthracene-11-carboxylic Acids
  作者：Charles D. Hurd、Albert Tockman

  DOI：10.1021/ja01510a025

  日期：1959.1
• Esters of anthracene acid adducts
  申请人：NEVILLE COMPANY

  公开号：US02511578A1

  公开（公告）日：1950-06-13
• Sarhan, Abd El-Wareth A.O.; El-Emary, Talaat I.; Hussein, Abdel Haleem M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 11, p. 1009 - 1015
  作者：Sarhan, Abd El-Wareth A.O.、El-Emary, Talaat I.、Hussein, Abdel Haleem M.

  DOI：——

  日期：——