methyl (S)-4-(((benzyloxy)carbonyl)amino)-3-oxo-5-phenylpentanoate | 65985-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (S)-4-(((benzyloxy)carbonyl)amino)-3-oxo-5-phenylpentanoate
• 英文别名: methyl (4S)-3-oxo-5-phenyl-4-(phenylmethoxycarbonylamino)pentanoate
• CAS: 65985-76-4
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: OGONXQXETKMYRO-KRWDZBQOSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  519.2±50.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (S)-4-(((benzyloxy)carbonyl)amino)-3-oxo-5-phenylpentanoate 在 盐酸 、 copper(l) iodide 、 caesium carbonate 、 L-脯氨酸 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 74.0h， 生成 methyl 2-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]-1H-indole-3-carboxylate
  参考文献：
  名称：

  Tetramic acids and indole derivatives from amino acid β-keto esters. Fine-tuning the conditions of the key Cu-catalyzed reaction

  摘要：

  1,3,5-Trisubstituted tetramic acids and 2,3-disubstituted indole derivatives were prepared from beta-keto esters derived from amino acids by their reaction with iodopheny1-2-trifluoroacetylamine under Cu-catalysis. Both heterocyclic systems were generated from the same starting materials by choice of the appropriate reaction conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.02.059
• 作为产物：
  描述：

  N-苄氧羰基-L-苯丙氨酸 在 Lewis acid 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 methyl (S)-4-(((benzyloxy)carbonyl)amino)-3-oxo-5-phenylpentanoate
  参考文献：
  名称：

  Mansour, Tarek S.; Evans, Colleen A., Synthetic Communications, 1990, vol. 20, # 5, p. 773 - 781

  摘要：

  DOI：

文献信息

• α-Amino acid derived enaminones and their application in the synthesis of N-protected methyl 5-substituted-4-hydroxypyrrole-3-carboxylates and other heterocycles
  作者：Uroš Grošelj、Mojca Žorž、Amalija Golobič、Branko Stanovnik、Jurij Svete

  DOI：10.1016/j.tet.2013.11.008

  日期：2013.12

  simple synthesis of novel N-protected methyl 5-substituted-4-hydroxypyrrole-3-carboxylates, which exist in equilibrium with their 4-oxo tautomers, has been developed in two steps starting from N-protected α-amino acids. The key intermediates are enaminones, which can also be isolated, characterized, and used for the construction of other functionalized heterocycles, before they spontaneously decompose

  的新颖的新的和简单的合成ñ -保护的5-取代-4-羟基吡咯-3-羧酸酯，其存在于与他们的4-氧代互变异构体平衡，已经在从开始的两个步骤被开发ñ -保护的α氨基酸。关键中间体是烯胺酮，其也被分离，表征，并用于其它官能化杂环的结构，才自发分解到吡咯产物。4-羟基吡咯易于部分空中氧化，但是可以有效地烷基化或还原成稳定的多取代的吡咯烷衍生物。
• New transient receptor potential TRPV1, TRPM8 and TRPA1 channel antagonists from a single linear β,γ-diamino ester scaffold
  作者：Paula Pérez-Faginas、M. Teresa Aranda、Roberto de la Torre-Martínez、Susana Quirce、Asia Fernández-Carvajal、Antonio Ferrer-Montiel、Rosario González-Muñiz

  DOI：10.1039/c5ra25709c

  日期：——

  screening campaign identified nine β,γ-diamino ester derivatives as TRP modulators. A discrete library of new derivatives (23 components) was prepared in a one-pot two step reductive amination reaction, and evaluated for their ability to block the agonist-induced calcium influx in cells expressing human TRPV1, TRPM8 and TRPA1 channels. Selective antagonists for each channel, as well as dual TRPV1/TRPM8

  高通量筛选活动确定了九种β，γ-二氨基酯衍生物作为TRP调节剂。在一锅两步还原胺化反应中制备了新衍生物（23个组分）的离散库，并评估了它们在表达人TRPV1，TRPM8和TRPA1通道的细胞中阻断激动剂诱导的钙内流的能力。在对该线性支架进行细微修饰之后，可获得每个通道的选择性拮抗剂以及双重TRPV1 / TRPM8和TRPM8 / TRPA1配体。SAR研究揭示了选择性阻断正在研究的三个TRP通道的优选取代基。最有效的TRPV1拮抗剂显示出亚微摩尔IC 50值。
• Synthesis and Transformations of Novel <scp>L</scp> -Phenylalanine Derived Pyrazolidin-3-ones
  作者：Uroš Grošelj、Amalija Golobič、Jurij Svete、Branko Stanovnik

  DOI：10.1002/chir.22166

  日期：2013.9

  A simple and straightforward four‐step synthesis of novel diastereomeric L‐phenylalanine‐derived pyrazolidin‐3‐ones is described. The absolute configuration of the novel C(5) stereogenic centre has been unambiguously determined by single crystal X‐ray analysis and via chemical interconversions. A series of novel thiourea derived pyrazolidinones have been prepared and tested as potential organocatalysts

  描述了一种新的非对映异构体L-苯丙氨酸衍生的吡唑烷定-3-酮的简单，简单的四步合成方法。新颖的C（5）立体生成中心的绝对配置已通过单晶X射线分析和通过化学互转换明确确定。已经制备了一系列新颖的硫脲衍生的吡唑烷酮并作为潜在的有机催化剂进行了测试。N（1）未取代的吡唑烷酮可用于构建新型双环杂环和其他选择性衍生化反应。手性25：541–555，2013年。©2013 Wiley Periodicals，Inc.
• MANSOUR, TAREK S.;EVANS, COLLEEN A., SYNTH. COMMUN, 20,(1990) N, C. 773-781
  作者：MANSOUR, TAREK S.、EVANS, COLLEEN A.

  DOI：——

  日期：——