methyl 2-tert-butoxycarbonylamino-4-methyl-3-oxopentanoate | 372965-15-6

• 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 2-tert-butoxycarbonylamino-4-methyl-3-oxopentanoate
• 英文别名: Methyl 4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopentanoate；methyl 4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopentanoate
• CAS: 372965-15-6
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: PPYWLPLIXVSTLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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 2-tert-butoxycarbonylamino-4-methyl-3-oxopentanoate 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 Methyl 2-acetamido-3-oxo-4-methylpentanoate
  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
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 N,N-二甲基丙烯基脲 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 8.0h， 生成 methyl 2-tert-butoxycarbonylamino-4-methyl-3-oxopentanoate
  参考文献：
  名称：

  Efficient enantioselective synthesis of (2R,3R)- and (2S,3S)-3-hydroxyleucines and their diastereomers through dynamic kinetic resolution

  摘要：

  (2R,3R)-和(2S,3S)-3-羟基亮氨酸是环状氨基肽、巴布酰胺和聚氧肽类化合物的组成部分，它们及其异构体可由相应的β-酮-α-氨基酸酯通过二氯化二钌双(萘基)苯并咪唑𬭩催化的动态动力学Z'分辨率氢化反应高效合成。 (C) 2001 Elsevier Science Ltd. 版权所有.

  DOI：

  10.1016/s0957-4166(01)00306-8

文献信息

• Efficient enantioselective synthesis of (2R,3R)- and (2S,3S)-3-hydroxyleucines and their diastereomers through dynamic kinetic resolution
  作者：Kazuishi Makino、Naoki Okamoto、Osamu Hara、Yasumasa Hamada

  DOI：10.1016/s0957-4166(01)00306-8

  日期：2001.7

  (2R,3R)- and (2S,3S)-3-Hydroxyleucines, components of cyclodepsipeptides, papuamides and polyoxypeptins, were efficiently synthesized along with their diastereomers from the corresponding beta -keto-alpha -amino acid ester through dynamic kinetic Z ' resolution using RuCl2(binap)-catalyzed hydrogenation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  (2R,3R)-和(2S,3S)-3-羟基亮氨酸是环状氨基肽、巴布酰胺和聚氧肽类化合物的组成部分，它们及其异构体可由相应的β-酮-α-氨基酸酯通过二氯化二钌双(萘基)苯并咪唑𬭩催化的动态动力学Z'分辨率氢化反应高效合成。 (C) 2001 Elsevier Science Ltd. 版权所有.
• 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.