Dimethyl rac-2,5-dibromoadipate

• 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 rac-2,5-dibromoadipate
• 英文别名: dimethyl rac-2,5-dibromohexanedioate；racem.-2,5-dibromo-adipic acid dimethyl ester；racem.-2,5-Dibrom-adipinsaeure-dimethylester；Racemischer 2,5-Dibrom-adipinsaeure-dimethylester；dimethyl (2R,5R)-2,5-dibromohexanedioate
• 化学式: C₈H₁₂Br₂O₄
• 分子量: 331.989
• InChiKey: HVICCJCVLLCDFQ-PHDIDXHHSA-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 rac-2,5-dibromoadipate 在 氯化亚砜 、 sodium methylate 、 potassium carbonate 作用下， 反应 35.0h， 生成 1-<(S)-1-Phenylethyl>-2,5-cis-bis(methoxycarbonyl)pyrrolidine
  参考文献：
  名称：

  A Convenient Synthesis of Enantiomeric Pairs of 2,5-Disubstituted Pyrrolidines of C₂-Symmetry

  摘要：

  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。

  DOI：

  10.1055/s-1993-25852
• 作为产物：
  描述：

  dimethyl (2R,5S)-2,5-dibromohexanedioate 生成 Dimethyl rac-2,5-dibromoadipate
  参考文献：
  名称：

  C 2对称反式-2,5-双（羟甲基）吡咯烷的两种对映体的合成。脂肪酶介导的顺序动力学拆分

  摘要：

  脂肪酶介导的顺序动力学拆分已被用于以光学纯的形式给出反式-2,5-双（羟甲基）吡咯烷的两种对映异构体。还报告了这些分辨率中不同参数对ee和产量的影响。

  DOI：

  10.1016/s0040-4039(00)73281-3

文献信息

• 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。
• Explorations into the Potential of Chiral Sulfonium Reagents to Effect Asymmetric Halonium Additions to Isolated Alkenes
  作者：Scott Snyder、Alexandria Brucks、Daniel Treitler、Shu-An Liu

  DOI：10.1055/s-0033-1338865

  日期：——

  While methods for the racemic dihalogenation and halohydroxylation of alkenes have been known for decades, enantioselective variants of these processes remain elusive. Initial attempts were made to overcome this long-standing challenge by exploring the potential of chiral, crystalline, sulfur-derived halonium reagents to accomplish the asymmetric dichlorination and iodohydroxylation of 1,2-dihydronaphthalene. Asymmetric dichlorination of this substrate was achieved in 57% yield and 14% enantiomeric excess (ee), but asymmetric iodohydroxylation was much more successful, giving 67% yield and 63% ee. Thorough studies were made of these processes, including investigation of various chiral sulfide derivatives, their substrate scopes, and the reaction conditions.
• Cyclobutane Derivatives. I.¹ The Degradation of cis- and trans-1,2-Cyclobutane-dicarboxylic Acids to the Corresponding Diamines
  作者：Edwin R. Buchman、Alf O. Reims、Thurston Skei、Maurice J. Schlatter

  DOI：10.1021/ja01263a048

  日期：1942.11
• Wille et al., Justus Liebigs Annalen der Chemie, 1957, vol. 608, p. 22,36
  作者：Wille et al.

  DOI：——

  日期：——
• 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。