N-(ethoxycarbonyl)-N-methyl-1-ethoxybenzylamine | 40848-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(ethoxycarbonyl)-N-methyl-1-ethoxybenzylamine
• 英文别名: ethyl N-(ethoxyphenylmethyl)-N-methylcarbamate；ethyl N-[ethoxy(phenyl)methyl]-N-methylcarbamate
• CAS: 40848-81-5
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: JCYIHQVDCUTMLT-UHFFFAOYSA-N

物化性质

• 沸点：
  313.3±31.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(ethoxycarbonyl)-N-methyl-1-ethoxybenzylamine 在 三氟化硼乙醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 trans-(E)-3-methyl-4-phenyl-5-(propen-1-yl)oxazolidin-2-one
  参考文献：
  名称：

  Allylstannation of N-acyliminium intermediates: a possible method for the stereocontrolled synthesis of polyhydroxypiperidines

  摘要：

  The stereochemistry of the allylstannation of acyliminium intermediates has been examined for gamma-alkoxyallyltins and gamma-silyloxyallyltributyltins. In the latter case, the reaction has been shown to afford cleanly the syn adduct. Its subsequent ring-closing metathesis and dihydroxylation has allowed the highly stereoselective preparation of a 2-aryl-trihydroxypiperidine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.027
• 作为产物：
  描述：

  苯亚甲基甲胺 以 苯 为溶剂， 生成 N-(ethoxycarbonyl)-N-methyl-1-ethoxybenzylamine
  参考文献：
  名称：

  Formation and Reactions of (1-Chloroalkyl)carbamoyl Chlorides. Synthesis of 1,2,4-Triazolidine-5-ones

  摘要：

  N-(α-氯苄基)羰酰氯和(α-氯苄基)甲基氨基甲酰氯分别由光气与N-苄亚胺和N-苄亚甲胺反应形成。描述了这些羰酰氯与许多亲核试剂的反应，其中一些导致苄基与氮之间的断裂，而另一些产生取代产物而不发生这种断裂。在后一种类型中，取代的肼反应以实现环闭合到1,2,4-三唑烷-5-酮。该方法作为这些新的杂环系统的便捷合成。

  DOI：

  10.1139/v73-048

文献信息

• The alkylation of α-ethoxycarbamates with organo-lead, -zinc, and -copper reagents. High cram selectivity and formal nonbasic alkylation of imines
  作者：Jun-ichi Yamada、Hisashi Satô、Yoshinori Yamamoto

  DOI：10.1016/s0040-4039(01)93812-2

  日期：1989.1

  The alkylation of α-ethoxycarbamates is accomplished with organo-lead, -zinc, and -copper reagents in the presence of Lewis acids. The reaction proceeds with high diastereoselectivity in good to high yields.

  α-乙氧基氨基甲酸酯的烷基化是在路易斯酸存在下用有机铅，-锌和-铜试剂完成的。反应以高的非对映选择性进行，产率高到高。
• syn-Allylstannation of N-Acyliminium Intermediates by Tributyl[γ-(silyloxy)allyl]stannanes: A Key Reaction for the Diastereoselective Synthesis of Polyhydroxypiperidines and Polyhydroxyazepanes
  作者：Floris Chevallier、Alexandre Lumbroso、Isabelle Beaudet、Erwan Le Grognec、Loïc Toupet、Jean-Paul Quintard

  DOI：10.1002/ejoc.201100302

  日期：2011.8

  The allylstannation of N-alkenyl N-acyliminium intermediates by tributyl[gamma-(silyloxy)allyl]stannanes afforded the expected adducts with a high syn-selectivity (up to 99: 1). Ensuing ring-closing metathesis afforded dehydropiperidines or dehydroazepanes which were engaged in a stereoselective dihydroxylation reaction leading to polyhydroxypiperidines or polyhydroxyazepanes in good yields. This sequence

  N-烯基N-酰基胺中间体通过三丁基[γ-(甲硅烷氧基)烯丙基]锡烷的烯丙基锡化提供了具有高顺式选择性(高达99:1)的预期加合物。随后的闭环复分解得到脱氢哌啶或脱氢氮杂环庚烷，它们参与立体选择性二羟基化反应，以良好的产率得到多羟基哌啶或聚羟基氮杂环庚烷。该序列被应用于 (+/-)-1-脱氧古洛糖野尻霉素的非对映选择性合成。
• The Lewis acid mediated reaction of carbamates with γ-oxygenated allyltin and its application to (±)-statine synthesis
  作者：Yoshinori Yamamoto、Martin Schmid

  DOI：10.1039/c39890001310

  日期：——

  The Lewis acid mediated reaction of acyliminium ions (6) with γ-oxygen substituted allyltin (1c) gave the amino alcohol derivatives (7) and/or (8) in good yields; in certain cases very high diastereoselectivity was achieved and the procedure was applied to the synthesis of (±)-statine.

  路易斯酸介导的丙烯酰亚胺离子（6）与γ-氧取代的烯丙基锡（1c）的反应以良好的收率得到了氨基醇衍生物（7）和/或（8）。在某些情况下，获得了很高的非对映选择性，并将该方法应用于（±）-他汀类药物的合成。
• Yamamoto, Yoshinori; Nakada, Tomohisa; Nemoto, Hisao, Journal of the American Chemical Society, 1992, vol. 114, # 1, p. 121 - 125
  作者：Yamamoto, Yoshinori、Nakada, Tomohisa、Nemoto, Hisao

  DOI：——

  日期：——
• Microwave-assisted synthesis of α-ethoxycarbamates
  作者：Alexandre Lumbroso、Floris Chevallier、Isabelle Beaudet、Jean-Paul Quintard、Thierry Besson、Erwan Le Grognec

  DOI：10.1016/j.tet.2009.09.023

  日期：2009.11

  An efficient and reproducible synthesis of various alpha-ethoxycarbamates is described via a microwave heating mode. Compared to the thermal process. the microwave dielectric heating induces a dramatic reduction of the reaction time and the improvement of the yields. The reaction is general since applicable to aromatic and aliphatic aldehydes with various primary amines. Several examples involving chiral aldehydes have also been considered. (C) 2009 Elsevier Ltd. All rights reserved.