bibenzyl-4,4'-dicarboxylic acid diethyl ester | 111977-60-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: bibenzyl-4,4'-dicarboxylic acid diethyl ester
• 英文别名: Bibenzyl-4,4'-dicarbonsaeure-diaethylester；4,4'-Dimethylenebis(ethyl benzoate)；ethyl 4-[2-(4-ethoxycarbonylphenyl)ethyl]benzoate
• CAS: 111977-60-7
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: BUGQXHPFTVMLSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bibenzyl-4,4'-dicarboxylic acid diethyl ester 在 盐酸 、 sodium azide 、 硫酸 、 硝酸 、 铁粉 、 sodium nitrite 作用下， 以 乙醇 、 邻二氯苯 为溶剂， 反应 12.25h， 生成 Diethyl 11H-indolo<1,2-b>indazole-3,8-dicarboxylate
  参考文献：
  名称：

  Synthesis and properties of diethyl 5,10-dihetera-5,10-dihydroindeno[2,1-a]indene-2,7-dicarboxylates

  摘要：

  A series of six heterocyclic diesters lb-6b containing all combinations of nitrogen, sulfur, and selenium has been prepared from a common precursor, diethyl 2,2'-dinitrostilbene-4,4'-dicarboxylate. Electrochemical analysis showed oxidation potential increases in the order N < Se < S, and the same trend was observed for maxima of UV absorbance. Electrochemical oxidation of indoloindole lb (but not the other members of the series) generates a persistent radical cation whose properties were investigated. Diesters containing sulfur and selenium (but not nitrogen) form S(A) liquid crystals. A new synthetic method leading to the indolo[1,2-b]indazole ring system has been found.

  DOI：

  10.1021/jo00071a034
• 作为产物：
  描述：

  对甲基苯甲酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 cobalt,triphenylphosphane,chloride 作用下， 以 乙酸乙酯 、 苯 为溶剂， 生成 bibenzyl-4,4'-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Aromatic aldehydes from benzylbromides via Cobalt(I) mediated benzyl radicals in the presence of aerial oxygen: a mild oxidation reaction in neutral condition

  摘要：

  Co(PPh3)(3)Cl has been shown to be a novel mediator Tor the conversion of benzylic bromides to aromatic aldehydes under mild conditions in the presence of aerial oxygen probably via benzylic radicals. In the absence of oxygen, the carbon-carbon coupling reactions bale been utilised to afford a series of functionalised benzylic dimers. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00110-5

文献信息

• Luminescent tungsten(<scp>vi</scp>) complexes as photocatalysts for light-driven C–C and C–B bond formation reactions
  作者：Daohong Yu、Wai-Pong To、Glenna So Ming Tong、Liang-Liang Wu、Kaai-Tung Chan、Lili Du、David Lee Phillips、Yungen Liu、Chi-Ming Che

  DOI：10.1039/d0sc01340d

  日期：——

  gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such as aryl chloride, reductive coupling of benzyl bromides for C–C bond formation, reductive coupling of phenacyl bromides, and decarboxylative coupling of redox-active esters of alkyl carboxylic acid with high product yields and broad functional group tolerance.

  光催化在实际合成应用中的实现取决于开发可大规模制备的廉价光催化剂。本文描述了一种空气稳定、吸收可见光的光致发光钨 ( VI ) 配合物，可以方便地以克级制备。该配合物可催化光化学有机转化反应，包括芳基卤化物（如芳基氯）的硼化反应、苄基溴还原偶联以形成 C-C 键、苯酰溴的还原偶联以及烷基羧酸的氧化还原活性酯与高产率和广泛的官能团耐受性。
• Synthesis of 3,7‐Disubstituted Imipramines by Palladium‐Catalysed Amination/Cyclisation and Evaluation of Their Inhibition of Monoamine Transporters
  作者：Helle Christensen、Christina Schjøth‐Eskesen、Marie Jensen、Steffen Sinning、Henrik H. Jensen

  DOI：10.1002/chem.201100885

  日期：2011.9.12

  describe a novel approach for the synthesis of a series of 3,7‐difunctionalised symmetric and unsymmetrical analogues of the tricyclic antidepressant (TCA) imipramine, which uses a key palladium‐catalysed amination/cyclisation of an ester‐functionalised dibromide. Of the ester, methyl, hydroxymethyl and methoxymethyl disubstituted compounds prepared, 3,7‐dimethyl‐imipramine was found to be the most potent

  我们描述了一种新的合成三环抗抑郁药（TCA）丙咪嗪的3,7-双官能化的对称和不对称类似物的新方法，该方法使用了关键的钯催化胺化/环化酯官能化的二溴化物。在所制备的酯，甲基，羟甲基和甲氧基甲基二取代的化合物中，发现3,7-二甲基亚胺基明对人类血清素转运蛋白（hSERT）最有效。发现3,7-二甲基丙咪嗪的抑制能力至少与母体丙咪嗪一样高。与人类去甲肾上腺素转运蛋白（hNET）相比，这种新型的TCA还具有更高的选择性（相对于丙咪嗪）与hSERT结合。3,7-二羟甲基丙咪嗪可以获得更高的选择性，发现它对hSERT的选择性比hNET高167倍，相对于母体丙咪嗪而言，选择性提高了120倍。这些结果进一步验证了我们先前的模型，即丙米嗪和丙米嗪的高亲和力类似物与hSERT的中央结合位点的结合。
• Reduction of benzylic halides with diethylzinc using tetrakis(triphenylphosphine)palladium as catalyst
  作者：Konstantinos A. Agrios、Morris Srebnik

  DOI：10.1021/jo00076a066

  日期：1993.11
• EP1997798
  申请人：——

  公开号：——

  公开（公告）日：——
• Metrod for Producing 1,2-Phenylethane Compound Using Atom Transfer Radical Coupling Reaction
  申请人：Niitani Takeshi

  公开号：US20090275772A1

  公开（公告）日：2009-11-05

  An object of the present invention is to provide a method capable of producing a 1,2-phenylethane compound with extremely high yield in a short amount of time. Disclosed is a method for producing a 1,2-phenylethane compound, which comprises subjecting a compound represented by formula (I): wherein Ra represents a hydrogen atom or a substituted or unsubstituted phenyl group; Rb represents a hydrogen atom or a substituent; n represents an integer of 1 to 5 and, when n is 2 or more, Rb may be the same or different, or may be combined with each other to form a ring; and X represents a halogen atom; to a coupling reaction in the presence of a transition metal complex to produce a compound represented by formula (II):