methyl 2-carbomethoxy-3-nitromethyl-4-methylpentanoate | 99190-18-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-carbomethoxy-3-nitromethyl-4-methylpentanoate
• 英文别名: (2-methyl-1-nitromethyl-propyl)-malonic acid dimethyl ester；(2-Methyl-1-nitromethyl-propyl)-malonsaeure-dimethylester
• CAS: 99190-18-8
• 化学式: C₁₀H₁₇NO₆
• 分子量: 247.248
• InChiKey: JLABTGNGXJMKBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  95.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3-methyl-1-nitro-but-1-ene 、 丙二酸二甲酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2-carbomethoxy-3-nitromethyl-4-methylpentanoate
  参考文献：
  名称：

  螺旋低聚脲折叠体作为强大的氢键催化剂用于对映选择性 CC 键形成反应

  摘要：

  对映选择性转化的无金属催化剂的开发取得了重大进展，但发现在低催化剂负载下有效的有机催化剂仍然是一个重大挑战。在这里，我们报告了一种新型协同催化剂组合系统，该系统由受肽启发的手性螺旋（硫）脲低聚物和简单的叔胺组成，能够促进可烯醇化羰基化合物和硝基烯烃之间的迈克尔反应，并具有极低的对映选择性（1/ 10 000) 手性催化剂/底物摩尔比。除了与螺旋折叠密切相关的高选择性之外，我们在此报告的系统也非常适合优化，因为它的每个组件都可以单独微调以提高反应速率和/或选择性。

  DOI：

  10.1021/jacs.7b05802

文献信息

• Axially Chiral Guanidine as Enantioselective Base Catalyst for 1,4-Addition Reaction of 1,3-Dicarbonyl Compounds with Conjugated Nitroalkenes
  作者：Masahiro Terada、Hitoshi Ube、Yusuke Yaguchi

  DOI：10.1021/ja057848d

  日期：2006.2.1

  introduction of an axially chiral binaphthyl backbone. The axially chiral guanidine catalysts thus developed facilitated the highly enantioselective 1,4-addition reaction of 1,3-dicarbonyl compounds with a broad range of conjugated nitroalkenes and showed extremely high catalytic activity.

  提出了一种设计手性胍分子的新策略，其特点是引入了轴向手性联萘骨架。由此开发的轴向手性胍催化剂促进了 1,3-二羰基化合物与多种共轭硝基烯烃的高度对映选择性 1,4-加成反应，并显示出极高的催化活性。
• Perekalin; Sobatschewa, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2905,2909; engl. Ausg. S. 2865, 2867
  作者：Perekalin、Sobatschewa

  DOI：——

  日期：——
• Mechanism and Application of a Microcapsule Enabled Multicatalyst Reaction
  作者：Sarah L. Poe、Muris Kobašlija、D. Tyler McQuade

  DOI：10.1021/ja071706x

  日期：2007.7.1

  In this paper, we describe the development and application of a multistep one-pot reaction that is made possible by the site isolation of two otherwise incompatible catalysts. We prepared a microencapsulated amine catalyst by interfacial polymerization and used it in conjunction with a nickel-based catalyst for the transformation of an aldehyde to a Michael adduct via a nitroalkene intermediate. The amine-catalyzed conversion of an aldehyde to a nitroalkene was found to proceed through an imine rather than a nitroalcohol. Kinetic studies indicated that the reaction is first order in both the nickel catalyst and the shell of the encapsulated amine catalyst. Furthermore, we provide evidence against interaction between amine and nickel catalysts and present kinetic data that demonstrates that there is a rate enhancement of the Michael addition due to the urea groups on the surface of the microencapsulated catalyst. We applied our one-pot reaction to the development of a new synthetic route for pregabalin that proceeds with an overall yield of 74%.