(+)-tert-butyl 3-amino-4-methylpentanoate

• 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: (+)-tert-butyl 3-amino-4-methylpentanoate
• 英文别名: (R)-3-amino-4-methylpentanoic acid tert-butyl ester；tert-butyl (3R)-3-amino-4-methylpentanoate
• 化学式: C₁₀H₂₁NO₂
• 分子量: 187.282
• InChiKey: VHVRAKSKDRWYIA-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+)-tert-butyl 3-(N-chloro-N-(mesitylmethyl)amino)-4-methylpentanoate 在 N-dibutylamino-DBU 、 盐酸羟胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 48.25h， 生成 (+)-tert-butyl 3-amino-4-methylpentanoate
  参考文献：
  名称：

  Chiral ligand-controlled asymmetric conjugate amination of enoates with lithium mesitylmethyl(trimethylsilyl)amide

  摘要：

  Lithium mesitylmethyl(trimethylsilyl)amide behaved as a nice amination agent in a chiral ligand-controlled conjugate addition reaction of tert-butyl cinnamate to give the conjugate amination product with 99% ee in 90% yield. Other acyclic and cyclic enoates were also aminated in reasonably high enantioselectivity, while the deprotonation of abstractable proton of enoates caused yield loss of the conjugate amination products, due to the bulkiness and enriched basicity of the lithium amide. Although such steric bulkiness made hard the hydrogenolytic cleavage of a mesitylmethyl-N bond of the adducts, a new protocol comprising N-chlorination-regioselective dehydro-chlorination-transoximation was developed for N-dearylmethylation, giving 3-aminoalkanoates in reasonably good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.040

文献信息

• Acylation of β-Amino Esters and Hydrolysis of β-Amido Esters: <i>Candida antarctica</i> Lipase A as a Chemoselective Deprotection Catalyst
  作者：Harri Mäenpää、Liisa T. Kanerva、Arto Liljeblad

  DOI：10.1002/cctc.201501381

  日期：2016.3.18

  tert‐butyl esters of 3‐amino‐3‐phenylpropanoic acid (E>100), 3‐amino‐4‐methylpentanoic acid (E>100) and 3‐aminobutanoic acid (E=60) on 1.0–2.0 m scale. With the N‐acylated resolution products, the exceptional ability of CAL‐A to hydrolyse amides and bulky tert‐butyl esters was then studied. In all N‐acylated tert‐butyl esters, chemoselectivity favoured the amide bond cleavage. The tert‐butyl ester bond was

  将南极假丝酵母（CAL-A）中的脂肪酶A在丁酸乙酯中进行N-酰化反应用于动力学拆分3-氨基-3-苯基丙酸（E > 100），3-氨基-4-甲基戊酸的叔丁基酯酸（E > 100）和3-氨基丁酸（E = 60），范围为1.0-2.0  m。然后，使用N-酰化的拆分产品，研究了CAL-A水解酰胺和大体积叔丁酯的出色能力。在所有的N-酰化的叔丁基酯中，化学选择性有利于酰胺键的裂解。该叔叔丁基酯键与3-氨基-3-苯基丙酸酯保持完整，而3-氨基-4-甲基戊酸酯和3-氨基丁酸酯则由CAL-A催化叔丁酯水解，然后再进行酰胺水解。
• Chiral ligand-controlled asymmetric conjugate amination of enoates with lithium mesitylmethyl(trimethylsilyl)amide
  作者：Takeo Sakai、Hirohisa Doi、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2006.06.040

  日期：2006.8

  Lithium mesitylmethyl(trimethylsilyl)amide behaved as a nice amination agent in a chiral ligand-controlled conjugate addition reaction of tert-butyl cinnamate to give the conjugate amination product with 99% ee in 90% yield. Other acyclic and cyclic enoates were also aminated in reasonably high enantioselectivity, while the deprotonation of abstractable proton of enoates caused yield loss of the conjugate amination products, due to the bulkiness and enriched basicity of the lithium amide. Although such steric bulkiness made hard the hydrogenolytic cleavage of a mesitylmethyl-N bond of the adducts, a new protocol comprising N-chlorination-regioselective dehydro-chlorination-transoximation was developed for N-dearylmethylation, giving 3-aminoalkanoates in reasonably good yields. (c) 2006 Elsevier Ltd. All rights reserved.