L-2-氯丁二酸 | 4198-33-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: L-2-氯丁二酸
• 中文别名: (S)-氯丁二酸
• 英文名称: (2S)-chlorobutanedioic acid
• 英文别名: (2S)-2-chlorosuccinic acid；(S)-2-chlorosuccinic acid；(S)-chlorosuccinic acid；L-2-chlorosuccinic acid；(S)-chlorosuccinic acid；(S)-Chlorbernsteinsaeure；(2S)-2-chlorobutanedioic acid
• CAS: 4198-33-8
• 化学式: C₄H₅ClO₄
• mdl: MFCD00067097
• 分子量: 152.534
• InChiKey: QEGKXSHUKXMDRW-REOHCLBHSA-N

物化性质

• 熔点：
  150-153 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  C
• 危险类别码：
  R34
• 危险品运输编号：
  UN 3261
• 海关编码：
  2917190090
• 安全说明：
  S26,S36/37/39,S45
• 储存条件：
  | 2-8°C |

反应信息

• 作为反应物：
  描述：

  L-2-氯丁二酸 在 硼烷四氢呋喃络合物 、 sodium hydroxide 、 三甲胺 作用下， 以 水 为溶剂， 反应 25.0h， 以50%的产率得到左旋肉碱
  参考文献：
  名称：

  Process for preparing R-(-) -carnitine from S-(-)-chlorosuccinic acid or from a derivative thereof

  摘要：

  一种L-肉碱的内盐是通过还原式制备的，使用合适的还原剂还原化合物(I)的公式，其中X1和X2可能相同或不同，是羟基，C1-C4烷氧基，苯氧基，卤素，或者X1和X2在一起时是氧原子，结果化合物是琥珀酐的衍生物; Y是卤素，甲烷磺氧基或对甲苯磺氧基; 然后用水处理，再用碱处理，最后加入三甲胺。

  公开号：

  US06677476B1
• 作为产物：
  描述：

  DL-天门冬氨酸 在 硫酸 、 potassium chloride 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 3.0h， 生成 L-2-氯丁二酸
  参考文献：
  名称：

  Identification and pharmacological characterization of succinate receptor agonists

  摘要：

  Background and PurposeThe succinate receptor (formerly GPR91 or SUCNR1) is described as a metabolic sensor that may be involved in homeostasis. Notwithstanding its implication in important (patho)physiological processes, the function of succinate receptors has remained ill‐defined because no pharmacological tools were available. We report on the discovery of the first family of potent synthetic agonists.Experimental ApproachWe screened a library of succinate analogues and analysed their activity on succinate receptors. Also, we modelled a pharmacophore and a binding site for this receptor. New agonists were identified based on the information provided by these two approaches. Their activity was studied in various bioassays, including measurement of cAMP levels, [Ca2+]i mobilization, TGF‐α shedding and recruitment of arrestin 3. The in vivo effects of activating succinate receptors with these new agonists was evaluated on rat BP.Key ResultsWe identified cis‐epoxysuccinic acid and cis‐1,2‐cyclopropanedicarboxylic acid as agonists with an efficacy similar to that of succinic acid. Interestingly, cis‐epoxysuccinic acid was 10‐ to 20‐fold more potent than succinic acid on succinate receptors. For example, cis‐epoxysuccinic acid reduced cAMP levels with a pEC50 = 5.57 ± 0.02 (EC50 = 2.7 μM), compared with succinate pEC50 = 4.54 ± 0.08 (EC50 = 29 μM). The rank order of potency of the three agonists was the same in all in vitro assays. Both cis‐epoxysuccinic and cis‐1,2‐cyclopropanedicarboxylic acid were as potent as succinate in increasing rat BP.Conclusions and ImplicationsWe describe new agonists at succinate receptors that should facilitate further research on this understudied receptor.

  DOI：

  10.1111/bph.13738

文献信息

• Preparation of Sephadex Derivatives with Optically Active Groups and Column-chromatographic Application to the Resolution of Some Cobalt(III) Complexes
  作者：Miho Fujita、Masanobu Sakano、Yuzo Yoshikawa、Hideo Yamatera

  DOI：10.1246/bcsj.54.3211

  日期：1981.10

  cation-exchangers were newly prepared as Sephadex derivatives derived from L-alanine, L-valine, L-aspartic acid, and L-threonine. They were applied to the column-chromatographic resolution of some cobalt(III) complexes, partial resolution being attained.

  光学活性阳离子交换剂被新制备为衍生自 L-丙氨酸、L-缬氨酸、L-天冬氨酸和 L-苏氨酸的 Sephadex 衍生物。它们被应用于某些钴 (III) 配合物的柱色谱分离，实现了部分分离。
• An Efficient Synthesis of Enantiomerically Pure (<i>R</i>)-(2-Benzyloxyethyl)oxirane from (<i>S</i>)-Aspartic Acid
  作者：Jeffrey A. Frick、John B. Klassen、Andreas Bathe、Jill M. Abramson、Henry Rapoport

  DOI：10.1055/s-1992-26176

  日期：——

  A 3-step synthesis of the title compound from (S)-aspartic acid is described. The overall yield of this process is 65% and the enantiomeric purity (ep) of the product is greater than 99%

  本文介绍了一种以 (S)- 天冬氨酸为原料的三步合成法。该工艺的总收率为 65%，产品的对映体纯度 (ep) 超过 99%。
• Holmberg, vol. 137, p. 21
  作者：Holmberg

  DOI：——

  日期：——
• Schlenk,W., Justus Liebigs Annalen der Chemie, 1973, p. 1156 - 1178
  作者：Schlenk,W.

  DOI：——

  日期：——
• Karrer; Reschofsky; Kaase, Helvetica Chimica Acta, 1947, vol. 30, p. 273
  作者：Karrer、Reschofsky、Kaase

  DOI：——

  日期：——

表征谱图