dimethyl (2R,5S)-2,5-dibromohexanedioate

• 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: dimethyl (2R,5S)-2,5-dibromohexanedioate
• 英文别名: dimethyl meso-2,5-dibromoadipate；dimethyl (2S,5R)-2,5-dibromohexanedioate
• 化学式: C₈H₁₂Br₂O₄
• 分子量: 331.989
• InChiKey: HVICCJCVLLCDFQ-OLQVQODUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  dimethyl (2R,5S)-2,5-dibromohexanedioate 在 potassium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.3h， 以95%的产率得到二甲基2,5-二溴己二酸酯
  参考文献：
  名称：

  Synthesis of new, highly hindered C2-symmetric trans-(2S,5S)-disubstituted pyrrolidines

  摘要：

  trans-(2S.5S)-(1,1-Diphenylmethyl)pyrrolidine has been prepared from the corresponding diester in four steps and 54% overall yield. Key steps involve the nucleophilic addition of an organomagnesium reagent to a carbonyl compound promoted by cerium(III) chloride and the reductive removal of benzylic trimethylsilyloxyl groups with Me3SiCl-Nal-MeCN and water. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00032-0
• 作为产物：
  描述：

  己二酰氯 在 溴 作用下， 以 甲醇 为溶剂， 生成 dimethyl (2R,5S)-2,5-dibromohexanedioate
  参考文献：
  名称：

  3,8-Diazabicyclo[3.2.1]octanes and their use in the treatment of cardiac arrhythmias

  摘要：

  提供了化合物的结构式（I），其中R1、R2和Ra到Rb的含义如描述中所示，在心律失常的预防和治疗中非常有用，特别是房性和室性心律失常。

  公开号：

  US20040023971A1

文献信息

• 3,8-Diazabicyclo[3.2.1]octanes and their use in the treatment of cardiac arrhythmias
  申请人：——

  公开号：US20040023971A1

  公开（公告）日：2004-02-05

  There is provided compounds of formula (I), wherein R 1 , R 2 and R a to R b have meanings given in the description, which are useful in the prophylaxis and in the treatment of arrhythmias, in particular atrial and ventricular arrhythmias.

  提供了化合物的结构式（I），其中R1、R2和Ra到Rb的含义如描述中所示，在心律失常的预防和治疗中非常有用，特别是房性和室性心律失常。
• Synthesis of a Conformationally Rigid Analogue of 2-Aminoadipic Acid ­Containing an 8-Azabicyclo[3.2.1]octane Skeleton
  作者：Pavel Mykhailiuk、Vladimir Kubyshkin、Anne Ulrich、Igor Komarov

  DOI：10.1055/s-0029-1216963

  日期：2009.10

  A new, conformationally rigid analogue of 2-amino­adipic acid, 8-[(benzyloxy)carbonyl]-3-methylene-8-azabicyclo[3.2.1]octane-1,5-dicarboxylic acid, is synthesized from dimethyl rac-2,5-dibromohexanedioate. The key steps involve alkylation-cyclization of 1-benzyl 2,5-dimethyl pyrrolidine-1,2,5-tricarboxylate with 3-chloro-2-(chloromethyl)prop-1-ene to yield the 8-azabicyclo[3.2.1]octane skeleton.

  一种新型构象刚性的2-氨基己二酸类似物，即8-[(苄氧基)羰基]-3-亚甲基-8-氮杂双环[3.2.1]辛烷-1,5-二羧酸，由外消旋二甲基2,5-二溴己二酸酯合成。关键步骤包括1-苄基2,5-二甲基吡咯烷-1,2,5-三羧酸酯与3-氯-2-(氯甲基)丙-1-烯的烷基化-环化反应，生成8-氮杂双环[3.2.1]辛烷骨架。
• A mechanochemical approach to access the proline–proline diketopiperazine framework
  作者：Nicolas Pétry、Hafid Benakki、Eric Clot、Pascal Retailleau、Farhate Guenoun、Fatima Asserar、Chakib Sekkat、Thomas-Xavier Métro、Jean Martinez、Frédéric Lamaty

  DOI：10.3762/bjoc.13.217

  日期：——

  Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline–proline dipeptides under solvent-free conditions. A deprotection–cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro–Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.

  球磨法被利用来通过机械化学亲核取代制备一个取代的脯氨酸构建块。随后，发展了受阻脯氨酸衍生物的机械偶联，以在无溶剂条件下提供脯氨酸-脯氨酸二肽。去保护-环化序列产生了相应的二酮哌嗪，其高立体选择性可以通过DFT计算来解释。使用这种方法，一个对映纯的二取代脯氨酸-脯氨酸二酮哌嗪在4个步骤中合成，利用了球磨机制造了5个新键。
• Synthesis of New Tetrazole-Substituted Pyroaminoadipic and Pipecolic Acid Derivatives
  作者：Fatimazohra Lenda、Farhate Guenoun、Bouchra Tazi、Najib Ben larbi、Hassan Allouchi、Jean Martinez、Fr�d�ric Lamaty

  DOI：10.1002/ejoc.200400328

  日期：2005.1

  Racemic 5-aryl- and 5-(arylmethyl)tetrazolyl-substituted pyroaminoadipic and pipecolic acid derivatives were diastereoselectively synthesized from dimethyl meso-2,5-dibromoadipate (1) in good yields under mild reaction conditions. The key step of this reaction sequence is the selective N2-alkylation of 5-substituted tetrazoles with 1. The reactive 2-bromo-5-tetrazolyladipate derivatives 2a−g were generated

  外消旋 5-芳基-和 5-（芳甲基）四唑基取代的焦氨基己二酸和哌可酸衍生物是在温和的反应条件下以良好的产率从二甲基内消旋-2,5-二溴己二酸 (1) 非对映选择性合成的。该反应序列的关键步骤是 5-取代四唑与 1 的选择性 N2-烷基化。 生成反应性 2-溴-5-四唑基己二酸酯衍生物 2a-g 并用叠氮化钠处理，然后进行 Pd/C 催化氢化, 提供内酰胺 4a-g。用 BH3 化学选择性还原 4a-g 的酰胺羰基，然后进行酸水解，提供外消旋形式的 5-四唑基哌啶酸。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• A Convenient Synthesis of Enantiomeric Pairs of 2,5-Disubstituted Pyrrolidines of C₂-Symmetry
  作者：Yukio Yamamoto、Jun'ichi Hoshino、Yukiko Fujimoto、Junko Ohmoto、Seiji Sawada

  DOI：10.1055/s-1993-25852

  日期：——

  By the use of (-)-1-phenylethylamine as a chiral auxiliary, three diastereomeric isomers of 2,5-bis(methoxycarbonyl)pyrrolidine derivatives are prepared from dimethyl rac-2,5-dibromoadipate and separated by crystallization and chromatographic fractionation involving stereoselective hydrolysis. The cis isomer is recovered and epimerized to the trans counterparts. Starting from each of the two trans isomers, optically active 2,5-disubstituted [2,5-bis(methoxymethyl) and 2,5-bis(methoxymethoxymethyl)] pyrrolidines of C 2-symmetry are synthesized by a short route.

  通过使用 (-)-1-苯基乙胺作为手性辅助剂，从二甲基阳离子-2,5-二溴己二酸酯制备了三种二叠体异构体的 2,5-双(甲氧基羧基)吡咯烷衍生物，并通过结晶和涉及立体选择性水解的色谱分离进行分离。收回顺式异构体并使其异构化为反式异构体。从每种反式异构体出发，通过一种简短的路线合成了具有 C2 对称性的光学活性 2,5-二取代的 [2,5-双(甲氧基甲基)和 2,5-双(甲氧基甲氧基甲基)] 吡咯烷。