methyl (E,2R)-2-acetamido-2-acetyl-5-phenylpent-4-enoate | 223561-11-3

• 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: methyl (E,2R)-2-acetamido-2-acetyl-5-phenylpent-4-enoate
• CAS: 223561-11-3
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: IMAUAKYJSONSBO-OJXHRBAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E,2R)-2-acetamido-2-acetyl-5-phenylpent-4-enoate 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Catalytic Asymmetric Allylation of Prochiral Nucleophiles, α-Acetamido-β-ketoesters

  摘要：

  DOI：

  10.1021/ja9900104
• 作为产物：
  描述：

  2-氨基-3-氧代丁酸甲酯 在 bis(η3-allyl-μ-chloropalladium(II)) 苯磺酰胺 、 potassium acetate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 methyl (E,2R)-2-acetamido-2-acetyl-5-phenylpent-4-enoate
  参考文献：
  名称：

  Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide

  摘要：

  A Pd-catalyzed enantio selective synthesis of quaternary alpha-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide is described. Asymmetric allylic substitution using acyclic beta-keto esters with a nitrogen functional group at the alpha-carbon as prochiral nucleophiles proceeded in the presence of 5 mol % of Pd catalyst, 10 mol % of chiral diaminophosphine oxide 1j, BSA, and appropriate additives, affording the corresponding quaternary alpha-amino acid derivatives in excellent yield and in up to 92% ee. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.020

文献信息

• Development of a New Class of Chiral Phosphorus Ligands:  P-Chirogenic Diaminophosphine Oxides. A Unique Source of Enantioselection in Pd-Catalyzed Asymmetric Construction of Quaternary Carbons
  作者：Tetsuhiro Nemoto、Takamasa Masuda、Takayoshi Matsumoto、Yasumasa Hamada

  DOI：10.1021/jo050800y

  日期：2005.9.1

  phosphorus compounds have been successfully applied to Pd-catalyzed asymmetric construction of tertiary and quaternary carbons. The actual ligand structure was the trivalent phosphorus species 17, which was generated in situ by BSA-induced P(V) to P(III) transformation of 6, the preligand. Detailed mechanistic studies, including asymmetric amplification and initial rate kinetics, revealed that complex 18

  我们最近开发了新的一类手性磷配体：P-手性二氨基膦氧化物。这些五价磷化合物已成功地应用于Pd催化的叔碳和季碳的不对称结构。实际的配体结构是三价磷物质17，它是由BSA诱导的6（前配体）的P（V）到P（III）转化原位生成的。详细的力学研究，包括不对称扩增和初始速率动力学，揭示了复杂的18 [Pd- 17（1：2）络合物]是活性催化剂。还阐明了配体侧臂上氮原子的重要功能。不对称季碳结构中对映体的来源是由N-Zn配位介导的次级配体底物相互作用。
• アミノエステル誘導体およびその製造方法
  申请人：——

  公开号：JP2000226362A

  公开（公告）日：2000-08-15

  (57)【要約】\n【課題】 α−アリル−α−アミノ−β−ケトエステル誘導体およびその製造方法を提供すること。\n【解決手段】 一般式（１）\n（式中、Ｒ1はアルキル、アリ−ル基を、Ｒ2はアルキルを、Ｒ3はアミノ基の保護基を、Ｒ4は水素、アルキル、アリ−ル。）で示されるα−アリル−α−アミノ−β−ケトエステル誘導体およびその製造方法。

  (57) [摘要] Јn [问题] 提供α-烯丙基-α-氨基-β-酮酯衍生物及其生产方法。\解】通式（1）Јn（式中，R1 为烷基、芳基，R2 为烷基，R3 为氨基的保护基，R4 为氢、烷基、芳基。α-烯丙基-α-氨基-β-酮酯衍生物及其生产方法如下所示。
• Applications of 4,4‘-(Me₃Si)₂-BINAP in Transition-Metal-Catalyzed Asymmetric Carbon−Carbon Bond-Forming Reactions
  作者：Masamichi Ogasawara、Helen L. Ngo、Takeshi Sakamoto、Tamotsu Takahashi、Wenbin Lin

  DOI：10.1021/ol050834s

  日期：2005.7.1

  A recently developed BINAP derivative with trimethylsilyl substituents on the 4- and 4 '-positions of the binaphthyl skeleton, 2,2 '-bis-(diphenylphosphino)-4,4 '-bis(trimethylsilyl)-1,1 '-binaphthyl (tms-BINAP), was used in a variety of transition-metal-catalyzed asymmetric carbon-carbon bond-forming reactions. In pi-allylpalladium-mediated reactions, tms-BINAP gave better enantioselectivity than the unsubstituted BINAP, and the origin of the improved enantioselectivity was gained from an X-ray structural study of [Pd(eta(3)-C3H5)((R)-tms-BINAP)]CIO4.
• Pd-catalyzed enantioselective synthesis of quaternary α-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide
  作者：Tetsuhiro Nemoto、Teisuke Harada、Takayoshi Matsumoto、Yasumasa Hamada

  DOI：10.1016/j.tetlet.2007.07.020

  日期：2007.9

  A Pd-catalyzed enantio selective synthesis of quaternary alpha-amino acid derivatives using a phenylalanine-derived P-chirogenic diaminophosphine oxide is described. Asymmetric allylic substitution using acyclic beta-keto esters with a nitrogen functional group at the alpha-carbon as prochiral nucleophiles proceeded in the presence of 5 mol % of Pd catalyst, 10 mol % of chiral diaminophosphine oxide 1j, BSA, and appropriate additives, affording the corresponding quaternary alpha-amino acid derivatives in excellent yield and in up to 92% ee. (c) 2007 Elsevier Ltd. All rights reserved.
• Catalytic Asymmetric Allylation of Prochiral Nucleophiles, α-Acetamido-β-ketoesters
  作者：Ryoichi Kuwano、Yoshihiko Ito

  DOI：10.1021/ja9900104

  日期：1999.4.1