(S)-methyl 5-chloro-3-methyl-5-oxopentanoate | 171598-61-1

• 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: (S)-methyl 5-chloro-3-methyl-5-oxopentanoate
• 英文别名: (S)-3-methyl-glutaric acid-chloride methyl ester；(S)-3-Methyl-glutarsaeure-chlorid-methylester；methyl (3S)-5-chloro-3-methyl-5-oxopentanoate
• CAS: 171598-61-1
• 化学式: C₇H₁₁ClO₃
• 分子量: 178.616
• InChiKey: UFNMBAXCMXCHAQ-RXMQYKEDSA-N

物化性质

• 沸点：
  223.1±23.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-methyl 5-chloro-3-methyl-5-oxopentanoate 在 氨 作用下， 生成 methyl (R)-3-methyl-4-carbamoylbutanoate
  参考文献：
  名称：

  Desymmetrization of dimethyl 3-substituted glutarates through enzymatic ammonolysis and aminolysis reactions

  摘要：

  The desymmetrization of differently 3-substituted glutarates through enzymatic aminolysis and ammonolysis has been studied. The effect of the diester and nucleophile structures, the enzymatic preparation as well as the reaction conditions have been compared in terms of both the chemical yield and enantiomeric excess of the corresponding monoamide products. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00869-8
• 作为产物：
  描述：

  3-甲基戊二酸酐 在 草酰氯 、 N,N-二甲基甲酰胺 、 奎宁 作用下， 以 二氯甲烷 、 氯苯 、 甲苯 为溶剂， 反应 3.0h， 生成 (S)-methyl 5-chloro-3-methyl-5-oxopentanoate
  参考文献：
  名称：

  基于非常规解离后有效的点对轴不对称诱导，由桥连的2-Arylindoles选择性合成N，C-Bis（二苯基膦）⊥。

  摘要：

  戊二酸酐的不对称甲醇分解和随后的6个步骤得到了具有99％ee的藜芦醇环抱的二甲基环庚烯酮非对映异构体；闭环是由一对非对映体δ-内酯的立体定向氢解所获得的羧酸的Friedel-Crafts酰化作用而发生的。所提及的环庚烯酮和Ph-NH-NH 2进行费歇尔吲哚合成，分别提供四环吲哚顺式和反式-14a。用BuLi进行的两次锂化反应和用ClPPh2进行的淬灭反应分别使二膦顺式和反式15具有完美的（P）-和（M）-atropselective选择性。

  DOI：

  10.1021/acs.orglett.9b03896

文献信息

• [EN] 5-OXO-ETE RECEPTOR ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS ANTAGONISTES DES RÉCEPTEURS 5-OXO-ETE
  申请人：UNIV MCGILL

  公开号：WO2010127452A1

  公开（公告）日：2010-11-11

  The present invention relates to novel pharmaceutically-useful compounds which are antagonists of the 5-oxo-ETE receptors, such as the OXE receptor. These compounds have use as therapeutic and/or prophylactic agents for diseases characterized by tissue eosinophilia, such as inflammatory conditions including respiratory diseases. The invention also relates to pharmaceutical compositions, to the use of such compounds and compositions as medicaments, and to therapeutic methods.

  本发明涉及一种新型的药用化合物，它们是5-oxo-ETE受体的拮抗剂，如OXE受体。这些化合物可用作治疗和/或预防组织嗜麻细胞增多等疾病的药物，如包括呼吸道疾病在内的炎症性疾病。该发明还涉及制药组合物，以及将这些化合物和组合物用作药物、以及治疗方法。
• Application of Chiral Pyrromethene–BF₂Complex Dye as a Fluorescent Labeling Reagent
  作者：Masaki Matsui、Kazumasa Funabiki、Ken-ichi Nakaya

  DOI：10.1246/bcsj.78.464

  日期：2005.3

  A chiral pyrromethene–BF2 complex dye, showing absorption (λmax) and emission maxima (λem) at 499 and 518 nm in acetonitrile, respectively, was synthesized. Racemic mexiletine smoothly reacted with this reagent in the presence of EDC to preferentially produce the corresponding diastereomeric amides, which were nicely separated by a non-chiral reverse phase column. The detection limit (S/N > 3) of mexiletine was ca. 0.3 pmol.

  合成了一种手性吡咯美烯–BF2复合染料，其在乙腈中分别在499 nm和518 nm处显示出最大吸收波长（λmax）和发射波长（λem）。无旋光性美克西利丁在EDC存在下与此试剂顺利反应，优先生成相应的二叠加异构体酰胺，这些酰胺通过非手性的反相柱很好地分离。美克西利丁的检测限（S/N > 3）约为0.3 pmol。
• Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of<i>meso</i>-cyclic anhydrides
  作者：Lingjun Xu、Shuwen Han、Linjie Yan、Haifeng Wang、Haihui Peng、Fener Chen

  DOI：10.3762/bjoc.14.19

  日期：——

  possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.

  研发了一系列新型的氯霉素基础酰胺有机催化剂，它们在C-1位置具有NH官能团作为单齿氢键供体，并评估了其对中环酸酐的对映选择性有机催化醇解作用。发现这些结构多样的有机催化剂在酸酐的醇解中诱导高对映选择性，并成功地用于（S）-GABOB的不对称合成。
• Highly Enantioselective Desymmetrization of <i>Meso</i> Anhydrides by a Bifunctional Thiourea-Based Organocatalyst at Low Catalyst Loadings and Room Temperature
  作者：Aldo Peschiulli、Yurii Gun'k、Stephen J. Connon

  DOI：10.1021/jo702639h

  日期：2008.3.1

  Bifunctional (thio)urea-based cinchona alkaloid derivatives have been shown to promote highly efficient enantioselective desymmetrization reactions of meso anhydrides. The most selective of these catalysts is capable of the enantioselective methanolysis of succinic and glutaric anhydride derivatives to form hemiester products with >90% yield and enantiomeric excess at 1 mol % loading and ambient temperature

  官能（硫代）脲基金鸡纳生物碱衍生物已经显示出促进高效的对映选择性desymmetrization反应内消旋酸酐。这些催化剂中最具选择性的是能够对琥珀酸和戊二酸酐衍生物进行对映选择性甲醇水解，以> 90％的收率和在1 mol％的负载量和环境温度下形成对映体过量的半酯产物。
• Stereoselective synthesis of two highly potent 5-oxo-ETE receptor antagonists
  作者：Chintam Nagendra Reddy、Qiuji Ye、Shishir Chourey、Sylvie Gravel、William S. Powell、Joshua Rokach

  DOI：10.1016/j.tetlet.2015.10.097

  日期：2015.12

  Enantioselective synthesis of highly potent 5-oxo-ETE receptor antagonists 5a and 6a with a high level of enantiomeric purity is described. The main feature of this work is the simple and efficient synthesis of the bi-functionalized 3-(S)-methyl-pentanedioic acid monomethyl ester (24) with the enantiomeric ratio of S/R:98.4/1.6. We investigated the asymmetric conjugate addition of MeMgBr to 5-Benzyloxy-pent-2-enoic

  描述了具有高水平对映体纯度的高效5-oxo-ETE受体拮抗剂5a和6a的对映选择性合成。这项工作的主要特点是简单有效地合成对映体比率为S / R：98.4 / 1.6的双官能化3-（S）-甲基戊二酸单甲酯（24）。我们研究了MeMgBr在CuBr /（S）-Tol-BINAP系统催化下的5-苯甲氧基-戊-2-烯酸甲酯（23）的不对称共轭加成反应，并优化了反应条件的区域选择性和高对映选择性。