ethyl 2-((4-methoxyphenyl)-amino)-4-oxopentanoate | 692733-26-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-((4-methoxyphenyl)-amino)-4-oxopentanoate
• 英文别名: Ethyl 2-(4-methoxyanilino)-4-oxopentanoate
• CAS: 692733-26-9
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: MIBZZGMYRFTUJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-((4-methoxyphenyl)-amino)-4-oxopentanoate 在 Lactobacillus brevis alcohol dehydrogenase 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以99%的产率得到
  参考文献：
  名称：

  Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis

  摘要：

  通过有机催化的Mannich反应和酶催化的酮还原，立体选择性合成了PMP-保护的γ-羟基去缬氨酸的所有四个对映异构体。

  DOI：

  10.1039/c4cc06230b
• 作为产物：
  描述：

  (2R)-ethyl-2-(p-methoxyphenylamino)-4-oxo-pentanoate 在 甲氧苯胺 作用下， 以 异丙醇 为溶剂， 生成 ethyl 2-((4-methoxyphenyl)-amino)-4-oxopentanoate
  参考文献：
  名称：

  Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis

  摘要：

  通过有机催化的Mannich反应和酶催化的酮还原，立体选择性合成了PMP-保护的γ-羟基去缬氨酸的所有四个对映异构体。

  DOI：

  10.1039/c4cc06230b

文献信息

• Cross-Dehydrogenative Coupling Reactions by Transition-Metal and Aminocatalysis for the Synthesis of Amino Acid Derivatives
  作者：Jin Xie、Zhi-Zhen Huang

  DOI：10.1002/anie.201004940

  日期：2010.12.27

  The direct approach: The title coupling reactions of N‐aryl glycine esters with unmodified ketones occurred smoothly in the presence of tert‐butyl hydroperoxide (TBHP) or 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) under mild conditions (see scheme). The oxidant used for CH activation determined the selectivity of the reactions for a particular type of ketone substrate.

  直接方法：在叔丁基氢过氧化物（TBHP）或2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）的存在下，N-芳基甘氨酸酯与未修饰的酮的标题偶联反应平稳进行）在温和的条件下（请参阅计划）。用于CH活化的氧化剂决定了对于特定类型的酮底物的反应选择性。
• Visible-Light-Promoted Cross Dehydrogenative/Decarboxylative Coupling Cascades of Glycine Ester Derivatives and β-Keto Acids
  作者：Chunhui Jiang、Xuefei Sha、Cheng Ni、Wei Qin、Xuejie Zhu、Shan Wang、Xuan Li、Hongfei Lu

  DOI：10.1021/acs.joc.2c00149

  日期：2022.7.1

  A visible-light-induced dehydrogenative/decarboxylative coupling reaction of arylglycine derivatives and β-keto acids is described. This photocatalyst- and additive-free protocol can be applied in the efficient synthesis of γ-keto glycine derivatives under ambient conditions. Further uses of this methodology and a plausible mechanism are also demonstrated.

  描述了芳基甘氨酸衍生物和β-酮酸的可见光诱导的脱氢/脱羧偶联反应。这种无光催化剂和无添加剂的方案可用于在环境条件下有效合成 γ-酮甘氨酸衍生物。还展示了该方法的进一步使用和合理的机制。
• Evidence for an Enol Mechanism in a Highly Enantioselective Mannich-Type Reaction Catalyzed by Primary Amine-Thiourea
  作者：Denis A. Yalalov、Svetlana B. Tsogoeva、Tatyana E. Shubina、Irina M. Martynova、Timothy Clark

  DOI：10.1002/anie.200800849

  日期：2008.8.18
• Insights into the spontaneous emergence of enantioselectivity in an asymmetric Mannich reaction carried out without external catalyst
  作者：Felix E. Held、Anja Fingerhut、Svetlana B. Tsogoeva

  DOI：10.1016/j.tetasy.2012.10.021

  日期：2012.12

  ESI-MS, chiral HPLC, time-resolved H-1 NMR and optical rotation measurements were performed to gain insights into the nature of spontaneous mirror symmetry breaking in the catalyst-free Mannich reaction of PMP protected alpha-iminoethylglyoxylate with hydroxyacetone. Spontaneous temporary generation of enantiomeric excesses of up to 7.4% in the major syn diastereomer is reproducibly observed in aqueous phosphate buffers, starting from achiral conditions. The syn-product ee values for both enantiomers [(2S,3S) and (2R,3R)], although not with stochastic distribution, have been observed with no clear preference for either enantiomer. (C) 2012 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis
  作者：Robert C. Simon、Eduardo Busto、Joerg H. Schrittwieser、Johann H. Sattler、Jörg Pietruszka、Kurt Faber、Wolfgang Kroutil

  DOI：10.1039/c4cc06230b

  日期：——

  Stereoselective synthesis of all four diastereomers of PMP-protected γ-hydroxynorvalineviaan organocatalytic Mannich reaction and an enzymatic ketone reduction.

  通过有机催化的Mannich反应和酶催化的酮还原，立体选择性合成了PMP-保护的γ-羟基去缬氨酸的所有四个对映异构体。