methyl 3-[hexyl(3-methoxy-3-oxopropyl)amino]propanoate | 167279-47-2

• 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 3-[hexyl(3-methoxy-3-oxopropyl)amino]propanoate
• 英文别名: 3,3'-(N-hexylimino)dipropionic acid dimethyl ester；Methyl 3-[hexyl-(3-methoxy-3-oxopropyl)amino]propanoate
• CAS: 167279-47-2
• 化学式: C₁₄H₂₇NO₄
• 分子量: 273.373
• InChiKey: RWODCMGCBCFLTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  341.5±27.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-[hexyl(3-methoxy-3-oxopropyl)amino]propanoate 在 盐酸 、 甲醇 、 sodium hydride 作用下， 以 苯 为溶剂， 反应 19.0h， 生成 1-己基四氢-4(1h)-吡啶酮
  参考文献：
  名称：

  Catalytic Epoxidation of Alkenes with Oxone

  摘要：

  A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed. The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group. Optimal epoxidation conditions employ 10 mol % of 1-dodecyl-1-methyl-4-oxopiperidinium triflate (8d(+)OTf(-)) in a CH2Cl2/pH 7.5-8.0 biphase using potassium monoperoxosulfate (Oxone) as the oxidant. Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5-8.0, (3) N-dodecyl chain, and (4) the triflate salt as key experimental and structural variables. A selection of nine olefins was successfully oxidized to the corresponding epoxides in 83-96% yield.

  DOI：

  10.1021/jo00110a049
• 作为产物：
  描述：

  正己胺 、 丙烯酸甲酯（MA） 以 甲醇 为溶剂， 反应 24.0h， 以98%的产率得到methyl 3-[hexyl(3-methoxy-3-oxopropyl)amino]propanoate
  参考文献：
  名称：

  Catalytic Epoxidation of Alkenes with Oxone

  摘要：

  A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed. The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group. Optimal epoxidation conditions employ 10 mol % of 1-dodecyl-1-methyl-4-oxopiperidinium triflate (8d(+)OTf(-)) in a CH2Cl2/pH 7.5-8.0 biphase using potassium monoperoxosulfate (Oxone) as the oxidant. Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5-8.0, (3) N-dodecyl chain, and (4) the triflate salt as key experimental and structural variables. A selection of nine olefins was successfully oxidized to the corresponding epoxides in 83-96% yield.

  DOI：

  10.1021/jo00110a049

文献信息

• Aza-Michael Reactions in Ionic Liquids. A Facile Synthesis of β-Amino Compounds
  作者：J. S. Yadav、B. V. S. Reddy、A. K. Basak、A. V. Narsaiah

  DOI：10.1246/cl.2003.988

  日期：2003.11

  Electron-deficient olefins undergo smoothly aza-Michael reactions with a wide range of amines in ionic liquids in the absence of any acid catalyst to produce the corresponding β-amino compounds in excellent yields with high 1,4-selectivity. The recovered ionic liquids can be reused in subsequent reactions without loss of activity. Owing to the high polarity of ionic liquids, the enones show enhanced reactivity thereby reducing reaction times and improving the yields significantly.

  缺电子烯烃在无任何酸催化剂的情况下，能顺利地在离子液体中与多种胺类进行aza-Michael反应，高效地生成高1,4-选择性的相应β-氨基化合物。回收的离子液体可在后续反应中重复使用，且活性无损失。由于离子液体的高极性，使得烯酮表现出增强的反应活性，从而缩短反应时间，显著提高产率。
• Carbon dioxide as a reversible amine-protecting agent in selective Michael additions and acylations
  作者：Annelies Peeters、Rob Ameloot、Dirk E. De Vos

  DOI：10.1039/c3gc40568k

  日期：——

  solution of a sufficiently basic primary amine at room temperature and atmospheric pressure. This reaction is employed for the protection of the amine functionality in several reactions at room temperature where inter- or intramolecular selectivity is desired. The concept is demonstrated for the selective Michael additions to methyl acrylate of a normally less reactive sulfonamide in the presence of a strong

  二氧化碳可以用作下列物质的临时保护基 胺类。一个氨基甲酸当CO 2鼓泡通过足够碱性的溶液时，可逆地形成伯胺在室温和大气压下。该反应在需要分子间或分子内选择性的室温下的几个反应中用于保护胺官能度。该概念已针对迈克尔的选择性添加而得到了证明。丙烯酸甲酯 通常反应性较小的 磺酰胺 在强大的存在下 胺 亲核试剂或环状 仲胺 在脂肪族存在下 伯胺，或在以下条件下存在的β-酮酸酯 胺类。选择性的酰化 的 酒精 在一个 胺也可以在CO 2气氛下实现。
• Uncatalyzed, green aza-Michael addition of amines to dimethyl maleate
  作者：Giovanna Bosica、Anthony John Debono

  DOI：10.1016/j.tet.2014.06.124

  日期：2014.9

  Dimethyl maleate was found to be a very reactive and selective acceptor for the aza-Michael addition in comparison to other commonly used electron-deficient alkenes. It reacts efficiently with a variety of aliphatic amines in complete absence of any catalyst and solvent at room temperature. Under these environmentally-friendly conditions, high yields of selectively mono-adducts were obtained within

  与其他常用的缺电子烯烃相比，发现马来酸二甲酯是氮杂-迈克尔加成反应的非常活泼和选择性的受体。在室温下，在完全不存在任何催化剂和溶剂的情况下，它可以与多种脂肪胺有效地反应。在这些环境友好的条件下，在短的反应时间内获得了高产率的选择性单加合物。
• Aza-Michael reaction: selective mono- versus bis-addition under environmentally-friendly conditions
  作者：Giovanna Bosica、Jonathan Spiteri、Caroline Borg

  DOI：10.1016/j.tet.2014.02.021

  日期：2014.4

  Aza-Michael reactions between primary amines and methyl propenoate have been investigated under environmentally-friendly solventless heterogeneous catalysis in order to obtain the mono- or the bis-adduct. The reaction conditions can be altered so as to maximise the yields of the required product with high selectivity. (C) 2014 Elsevier Ltd. All rights reserved.
• Catalytic Epoxidation of Alkenes with Oxone
  作者：Scott E. Denmark、David C. Forbes、David S. Hays、Jeffrey S. DePue、Richard G. Wilde

  DOI：10.1021/jo00110a049

  日期：1995.3

  A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed. The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group. Optimal epoxidation conditions employ 10 mol % of 1-dodecyl-1-methyl-4-oxopiperidinium triflate (8d(+)OTf(-)) in a CH2Cl2/pH 7.5-8.0 biphase using potassium monoperoxosulfate (Oxone) as the oxidant. Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5-8.0, (3) N-dodecyl chain, and (4) the triflate salt as key experimental and structural variables. A selection of nine olefins was successfully oxidized to the corresponding epoxides in 83-96% yield.