(S)-2-Acetylamino-2-phenyl-pent-4-enoic acid methyl ester | 848829-40-3

• 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: (S)-2-Acetylamino-2-phenyl-pent-4-enoic acid methyl ester
• 英文别名: methyl 2-acetamido-2-phenylpent-4-enoate
• CAS: 848829-40-3
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: XGTGOFZMINTNJH-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Acetylamino-2-phenyl-pent-4-enoic acid methyl ester 在 碘 作用下， 以 醋酸异丙酯 、 水 为溶剂， 以90%的产率得到(S)-4-Acetoxy-2-phenyl-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of 4-hydroxy-2-phenylproline framework

  摘要：

  Highly diastercoselective (>20:1) bromo-lactonization of N-sulfonyl-2-allyl-2-phenylglycine methyl ester (11) was observed. Successive treatment of the chiral lactone with MeONa gave the desired (2S,4R)-4-hydroxy-2-phenylproline derivative in high yield without erosion of the diastereoselectivity. The starting chiral non-racemic compound (5) was prepared from the racemic 2-phenylglycine using a classical kinetic resolution (crystallization), an asymmetric phase transfer alkylation, and an enzyme-catalyzed kinetic resolution. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.130
• 作为产物：
  描述：

  (S)-2-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-pent-4-enoic acid tert-butyl ester 在 硫酸 作用下， 以 碳酸氢钠 、 乙酸乙酯 为溶剂， 生成 (S)-2-Acetylamino-2-phenyl-pent-4-enoic acid methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of 4-hydroxy-2-phenylproline framework

  摘要：

  Highly diastercoselective (>20:1) bromo-lactonization of N-sulfonyl-2-allyl-2-phenylglycine methyl ester (11) was observed. Successive treatment of the chiral lactone with MeONa gave the desired (2S,4R)-4-hydroxy-2-phenylproline derivative in high yield without erosion of the diastereoselectivity. The starting chiral non-racemic compound (5) was prepared from the racemic 2-phenylglycine using a classical kinetic resolution (crystallization), an asymmetric phase transfer alkylation, and an enzyme-catalyzed kinetic resolution. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.130

文献信息

• Chemo- and Enantioselective Pd/B Hybrid Catalysis for the Construction of Acyclic Quaternary Carbons: Migratory Allylation of <i>O</i>-Allyl Esters to α-<i>C</i>-Allyl Carboxylic Acids
  作者：Taiki Fujita、Tomohiro Yamamoto、Yuya Morita、Hongyu Chen、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/jacs.8b02783

  日期：2018.5.9

  We describe herein the asymmetric synthesis of α-allyl carboxylic acids containing an α-quaternary stereocenter by a chiral hybrid catalyst system comprising palladium and boron complexes. The reaction proceeded through palladium-catalyzed ionization of α,α-disubstituted O-allyl esters for the generation of chiral π-allyl palladium complex as an electrophile, boron-catalyzed enolization of the carboxylate

  我们在本文中描述了通过包含钯和硼配合物的手性混合催化剂体系不对称合成含有 α-季铵立体中心的 α-烯丙基羧酸。该反应通过钯催化的 α,α-二取代 O-烯丙酯电离生成手性 π-烯丙基钯配合物作为亲电试剂，硼催化羧酸部分的烯醇化生成手性 α,α-二取代羧酸衍生的烯醇化物作为亲核试剂，以及由此产生的亲核试剂和亲电子试剂之间的对映选择性偶联。硼和钯催化剂的手性配体的适当组合至关重要。反应在羧酸基团的 α 位进行化学选择性。