(meso)-2,3-dibromosuccinic acid methyl ester | 17582-64-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (meso)-2,3-dibromosuccinic acid methyl ester
• 英文别名: dimethyl ester of meso-dibromosuccinic acid；Dimethyl-meso-2,3-dibromosuccinate；dimethyl meso-2,3-dibromosuccinate；meso-dimethyl-2,3-dibromosuccinate；meso-2,3-dibromodimethylsuccinate；dl-dimethyl 2,3-dibromosuccinate；dimethyl (2S,3R)-2,3-dibromobutanedioate
• CAS: 17582-64-8
• 化学式: C₆H₈Br₂O₄
• 分子量: 303.935
• InChiKey: XQBOXCHKENCESQ-ZXZARUISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (meso)-2,3-dibromosuccinic acid methyl ester 在 lithium bromoplumbite hydrate 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 dimethyl 2-bromofumarate
  参考文献：
  名称：

  A mild and selective dehydrohalogenating agent

  摘要：

  A discriminating reagent has been discovered which effects E2 elimination of HX from relatively reactive substrates. Readily prepared from lead(II) oxide and lithium bromide hydrate, this compound is a hydrated lithium dibromoplumbite. (C) 1997 Elsevier Science S.A.

  DOI：

  10.1016/s0022-1139(97)00014-6
• 作为产物：
  描述：

  马来酸二甲酯 在 溴 作用下， 生成 (meso)-2,3-dibromosuccinic acid methyl ester
  参考文献：
  名称：

  Anschuetz, Chemische Berichte, 1879, vol. 12, p. 2281

  摘要：

  DOI：

文献信息

• Reductive dehalogenation of aliphatic vic-dihalides with metallic samarium in a methanolic medium
  作者：Reiko Yanada、Nobuyuki Negoro、Kazuo Yanada、Tetsuro Fujita

  DOI：10.1016/s0040-4039(97)82951-6

  日期：1996.12

  In the title reaction, eight vic-dibromides and three vinylene dibromides gave the corresponding debromination products (alkenes and alkynes) at room temperature under neutral condition and an argon atmosphere. 2,3-Dibromosuccinic acid derivatives gave overreduction products or an unusual coupling dimer.

  在标题反应，八个VIC -dibromides和三个亚乙烯基二溴化物，得到在室温下相应的脱溴产物（烯烃和炔烃）中性条件和氩气气氛下。2,3-二溴丁二酸衍生物产生过度还原的产物或异常的偶联二聚体。
• Halocarbocyclization versus dihalogenation: substituent directed iodine(<scp>iii</scp>) catalyzed halogenations
  作者：Maciej Stodulski、Alissa Goetzinger、Stefanie V. Kohlhepp、Tanja Gulder

  DOI：10.1039/c3cc49850f

  日期：——

  The nucleophilicity of the substituents in iodobenzene pre-catalysts have a huge impact on product selectivity in iodine(III) triggered halogenations, steering the reactivity from solely carbocyclizations towards dihalogenations. Utilizing this catalyst-dependent reactivity a diastereo- and chemoselective dihalogenation method was established allowing the conversion of structurally and electronically

  碘苯预催化剂中取代基的亲核性对碘（III）引发的卤化反应中的产物选择性产生巨大影响，使反应性从单纯的碳环化转向二卤化。利用这种依赖于催化剂的反应性，建立了非对映和化学选择性二卤化方法，该方法可以以优异的产率转化结构上和电子上不同的不饱和化合物。
• Chemoselective and Stereoselective Debromination of Vicinal-Dibromides with Sodium Dithionite
  作者：Jitender M. Khurana、Arti Sehgal

  DOI：10.1080/00397919608003795

  日期：1996.10

  Abstract A simple and effcient procedure for the quantitative debromination of vic-dibromides has been reported with sodium dithionite at ambient temperature. These eliminations are chemoselective and also stereoselective.

  摘要 已经报道了一种在环境温度下用连二亚硫酸钠定量脱溴的简单有效的方法。这些消除是化学选择性的，也是立体选择性的。
• Synthesis of 1,2,3,4,5-Penta(methoxycarbonyl)cyclopentadienides through Electrocyclic Ring Closure and Ring Contraction Reactions
  作者：Rinat F. Salikov、Konstantin P. Trainov、Dmitry N. Platonov、Alexander Yu. Belyy、Yury V. Tomilov

  DOI：10.1002/ejoc.201800732

  日期：2018.9.30

  Formation of the key‐intermediate in the synthesis of cyclohetadienes, which are precursors to penta(methoxycarbonyl)cyclopentadienyl potassium is proven. Dimethyl dibromosuccinate is proposed to be used instead of conventional dimethyl acetylenedicarboxylate in their synthesis. A new preparation of penta(methoxycarbonyl)cyclopentadienyl sodium by reducing hepta(methoxycarbonyl)cycloheptatriene is

  已证明在环戊二烯的合成中是关键中间体，环戊二烯是五（甲氧基羰基）环戊二烯基钾的前体。提议在合成中使用二溴二琥珀酸二甲酯代替常规的乙炔二羧酸二甲酯。报道了一种通过还原七（甲氧基羰基）环庚三烯而制备五（甲氧基羰基）环戊二烯基钠的新方法。
• Chemoselective Reduction of Vicinal-Dihalides with Mg-MeOH<i>via</i>SET
  作者：Jitender M. Khurana、Amita Gogia neé Puri、Ramesh K. Bankhwal

  DOI：10.1080/00397919708004093

  日期：1997.5

  Chemoselective reductions of vic-dihalides conjugated to a phenyl and/or an ester group are being reported with Mg-MeOH at ambient temperature. However, reactions with Mg-MeOH-THF led to the formation of alkenes predominantly. The reactions are proposed to proceed by SET from Mg.

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