2-苄基-3-羧基丙酸叔丁酯 | 125470-05-5

• 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: 2-苄基-3-羧基丙酸叔丁酯
• 英文名称: tert-butyl 2-benzylsuccinate
• 英文别名: 3-benzyl-4-(tert-butoxy)-4-oxobutanoic acid；2-benzyl-3-carboxypropionic acid t-butyl ester；3-Benzyl-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid
• CAS: 125470-05-5
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: ZVZVJDYXMTUDLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-苄基-3-羧基丙酸叔丁酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以95%的产率得到2-苄基丁二酸
  参考文献：
  名称：

  Synthesis of Monosubstituted Succinic Acids from tert-Butylsuccinate

  摘要：

  我们报道了叔丁基琥珀酸二负离子的制备及其烷基化反应。这种烷基化反应已被证明是制备单取代琥珀酸及其酸酐的有用方法。

  DOI：

  10.1055/s-2000-7110
• 作为产物：
  描述：

  单叔丁基琥珀酸酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 26.0h， 以52%的产率得到2-苄基-3-羧基丙酸叔丁酯
  参考文献：
  名称：

  Synthesis of Monosubstituted Succinic Acids from tert-Butylsuccinate

  摘要：

  我们报道了叔丁基琥珀酸二负离子的制备及其烷基化反应。这种烷基化反应已被证明是制备单取代琥珀酸及其酸酐的有用方法。

  DOI：

  10.1055/s-2000-7110

文献信息

• Biosynthesis of the Carbonylmethylene Structure Found in the Ketomemicin Class of Pseudotripeptides
  作者：Junpei Kawata、Taiki Naoe、Yasushi Ogasawara、Tohru Dairi

  DOI：10.1002/anie.201611005

  日期：2017.2.13

  We recently discovered novel pseudotripeptides, the ketomemicins, which possess a C‐terminal pseudodipeptide connected with a carbonylmethylene instead of an amide bond, through heterologous expression of gene clusters identified in actinobacteria. The carbonylmethylene structure is a stable isostere of the amide bond and its biological significance has been shown in several natural and synthetic products

  我们最近发现了新的假三肽，即酮米霉素，其通过在放线菌中鉴定出的基因簇的异源表达，具有与羰基亚甲基而不是酰胺键连接的C端假二肽。羰基亚甲基结构是酰胺键的稳定等位异构体，其生物学意义已在几种天然和合成产物中显示出来。尽管这些化合物具有生物学重要性，但对于如何生物合成羰基亚甲基结构知之甚少。在这项工作中，我们充分表征了假二肽的生物合成机制。醛缩酶，脱水酶，依赖PLP的甘氨酸C-乙酰基转移酶和脱氢酶参与了假二肽的形成，丙二酰辅酶A和丙酮酸苯酯为起始底物。
• Heterocyclic modulators of PKB
  申请人：ZENG Qingping

  公开号：US20090275592A1

  公开（公告）日：2009-11-05

  The invention relates to heterocyclic compounds of Formula I and compositions thereof useful for treating diseases mediated by protein kinase B (PKB) where the variables have the definitions provided herein. The invention also relates to the therapeutic use of such compounds and compositions thereof in treating disease states associated with abnormal cell growth, cancer, inflammation, and metabolic disorders.

  本发明涉及一种公式I的杂环化合物及其组合物，其中变量具有本文所提供的定义，其在治疗由蛋白激酶B（PKB）介导的疾病方面具有用途。本发明还涉及这种化合物和组合物在治疗与异常细胞生长、癌症、炎症和代谢紊乱相关的疾病状态方面的治疗用途。
• COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERS
  申请人：Hoveyda Hamid

  公开号：US20110230477A1

  公开（公告）日：2011-09-22

  The present invention is directed to novel compounds of formula (I) and their use in treating metabolic diseases.

  本发明涉及式（I）的新化合物及其在治疗代谢性疾病方面的应用。
• Optical 2-benzyl-5-hydroxy-4-oxopentanoic acids against carboxypeptidase A: Synthesis, kinetic evaluation and X-ray crystallographic study
  作者：Shou Feng Wang、Jing-Yi Jin、Zong Hao Zeng、Guan Rong Tian

  DOI：10.1016/j.cclet.2009.09.005

  日期：2010.2

  2-Benzyl-5-hydroxy-4-oxopentanoic acid 1 and its enantiomers were designed, synthesized and assayed for inhibitory activity against carboxypeptidase A (CPA, EC 3.4.17.1). To verify the role of the terminal hydroxyl group in 1 binding to CPA, 2-benzyl-5-benzyloxy-4-oxopentanoic acid 2 was also synthesized and evaluated. The inhibition constants show that both L-1 and D-1 were shown to have strong binding affinity with L-1 being more potent than its enantiomer by 165-fold. On the other hand, the inhibition constant of 2 increases 4-fold comparing with that of 1. In order to explore the exact binding mode of the hydroxyacteyl group of 1 to the active site zinc ion of CPA, we have solved the crystal structure of CPA complexed with L-1 up to 1.85 A resolution. In CPA-L-1 complex, the phenyl ring is fitted in the substrate recognition pocket at the S, subsite, and the carboxylate forms bifurcated hydrogen bonds with the guanidinium moiety of Arg-145 and Arg-127 and a hydrogen bond with the phenolic hydroxyl of the down-positioned Tyr-248. The carbonyl oxygen of L-1 does coordinate to the active site zinc ion of CPA as expectedly. Unexpectedly, the terminal hydroxyl group of L-1 is engaged in hydrogen bonding with carbonyl oxygen of Ser-197 instead of coordinating to the active site zinc ion. (C) 2009 Guan Rong Tian. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All fights reserved.
• HETEROCYCLIC MODULATORS OF PKB
  申请人：Amgen Inc.

  公开号：EP2173728A2

  公开（公告）日：2010-04-14