(±)-methyl 4-(tert-butoxycarbonyl)amino-3-methylbutanoate

• 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 4-(tert-butoxycarbonyl)amino-3-methylbutanoate
• 英文别名: 4-t-butoxycarbonylamino-3.3-dimethyl-butyric acid methyl ester；Methyl 4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methylbutanoate；methyl 3-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: CBSWQPBHPCWSAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (±)-methyl 4-(tert-butoxycarbonyl)amino-3-methylbutanoate 在 sodium hydroxide 、 三氟乙酸 作用下， 生成 (4S)-4-甲基吡咯烷酮-2-酮 、 (R)-(+)-4-methylpyrrolidin-2-one
  参考文献：
  名称：

  Cycloaddition Reactions of Chiral 2-Amino-1,3-butadienes with Nitroalkenes:  Synthesis of Enantiomerically Pure 4-Nitrocyclohexanones¹

  摘要：

  2-Amino-1,3-butadienes bearing commercially available S-(+)-2-(methoxymethyl)pyrrolidine as chiral auxiliary undergo a [4 + 2] cycloaddition reaction with nitroalkenes to furnish 4-nitrocyclohexanones upon hydrolysis of the resulting enamine. The cycloadducts are obtained with good yields and very high enantiomeric excesses. The reaction has been performed with aromatic and aliphatic conjugated nitroalkenes. Moreover, a 2-amino diene which features a (Z) double bond undergoes a Michael addition reaction with nitroalkenes, which gives rise to open chain compounds with high enantioselectivity. After acidic hydrolysis, the open chain compounds cyclize to form chiral substituted furans.

  DOI：

  10.1021/jo970237m
• 作为产物：
  描述：

  巴豆酸甲酯 在 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、413.7 kPa 条件下， 反应 6.25h， 生成 (±)-methyl 4-(tert-butoxycarbonyl)amino-3-methylbutanoate
  参考文献：
  名称：

  取代基和氨基位置对 γ-氨基酯的脂肪酶催化拆分的影响：一项揭示南极假丝酵母脂肪酶 B 对映选择性的分子对接研究

  摘要：

  与N保护的 β 3氨基酯相比，南极念珠菌脂肪酶 B 催化的氨基酯的动力学拆分具有 α ( γ 2 )、β ( γ 3 ) 和 γ ( γ 4 ) 立体中心，在催化腔的高度。分子对接研究有助于确定空间排斥区域涉及 Ile189 和 Val190 残基以及氨基键合区域，其中有利于与 Asp134 残基的氢键。

  DOI：

  10.1002/ejoc.202100712

文献信息

• SUBSTITUTED AZAINDOLE COMPOUNDS, SALTS, PHARMACEUTICAL COMPOSITIONS THEREOF AND METHODS OF USE
  申请人：Sunshine Lake Pharma Co., Ltd.

  公开号：US20140056849A1

  公开（公告）日：2014-02-27

  The present invention provides substituted azaindole prodrugs, methods of making said prodrugs, pharmaceutical compositions of said prodrugs and methods of using said prodrugs and pharmaceutical compositions thereof to treat or prevent diseases or disorders such as cancer.

  本发明提供了替代的氮杂吲哚前药，制备该前药的方法，包括该前药的药物组合物以及使用该前药和药物组合物来治疗或预防癌症等疾病或疾病的方法。
• US9399639B2
  申请人：——

  公开号：US9399639B2

  公开（公告）日：2016-07-26
• [EN] HYDROXAMIC ACID DERIVATIVES, PREPARATION AND THERAPEUTIC USES THEREOF<br/>[FR] DÉRIVÉS D'ACIDE HYDROXAMIQUE, PRÉPARATION ET UTILISATIONS THÉRAPEUTIQUES DE CEUX-CI
  申请人：KHAN AMIN

  公开号：WO2010065709A2

  公开（公告）日：2010-06-10

  Disclosed are amino alkyl/aryl hydroxamic acid compounds and pharmaceutical compositions containing such compounds. The disclosed compositions are useful as therapeutics for degenerative diseases in mammal.
• Cycloaddition Reactions of Chiral 2-Amino-1,3-butadienes with Nitroalkenes:  Synthesis of Enantiomerically Pure 4-Nitrocyclohexanones¹
  作者：José Barluenga、Fernando Aznar、Cristina Ribas、Carlos Valdés

  DOI：10.1021/jo970237m

  日期：1997.10.1

  2-Amino-1,3-butadienes bearing commercially available S-(+)-2-(methoxymethyl)pyrrolidine as chiral auxiliary undergo a [4 + 2] cycloaddition reaction with nitroalkenes to furnish 4-nitrocyclohexanones upon hydrolysis of the resulting enamine. The cycloadducts are obtained with good yields and very high enantiomeric excesses. The reaction has been performed with aromatic and aliphatic conjugated nitroalkenes. Moreover, a 2-amino diene which features a (Z) double bond undergoes a Michael addition reaction with nitroalkenes, which gives rise to open chain compounds with high enantioselectivity. After acidic hydrolysis, the open chain compounds cyclize to form chiral substituted furans.
• Effect of the Substituent and Amino Group Position on the Lipase‐Catalyzed Resolution of γ‐Amino Esters: A Molecular Docking Study Shedding Light on<i>Candida antarctica</i>lipase B Enantioselectivity
  作者：Marina A. Ortega‐Rojas、Edmundo Castillo、Rodrigo Said Razo‐Hernández、Nina Pastor、Eusebio Juaristi、Jaime Escalante

  DOI：10.1002/ejoc.202100712

  日期：2021.9.14

  In contrast to N-protected β3-amino esters, the Candida antarctica lipase B catalyzed kinetic resolution of amino esters holding alpha (γ2), beta (γ3), and gamma (γ4) stereocenters is strongly compromised by steric factors at the level of the catalytic cavity. Molecular docking studies helped establish that the steric exclusion region involves the Ile189 and Val190 residues and the amino bonding region

  与N保护的 β 3氨基酯相比，南极念珠菌脂肪酶 B 催化的氨基酯的动力学拆分具有 α ( γ 2 )、β ( γ 3 ) 和 γ ( γ 4 ) 立体中心，在催化腔的高度。分子对接研究有助于确定空间排斥区域涉及 Ile189 和 Val190 残基以及氨基键合区域，其中有利于与 Asp134 残基的氢键。