benzyl methyl(vinyl)carbamate

• 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: benzyl methyl(vinyl)carbamate
• 英文别名: benzyl N-ethenyl-N-methylcarbamate
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: MPHKOEUYAOYCDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl methyl(vinyl)carbamate 、 a-叠氮基-苯乙酸甲酯 在 copper acetylacetonate 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以60%的产率得到rel-(1R,2S)-methyl 2-(((benzyloxy)carbonyl)(methyl)amino)-1-phenylcyclopropanecarboxylate
  参考文献：
  名称：

  Copper(II)–acid catalyzed cyclopropanation of 1,3-dienamides by electrophilic activation of α-aryl diazoesters

  摘要：

  Copper(II)-acid catalyzed cyclopropanation of electron-rich alkenes, such as 1,3-dienamides, with cc-aryl diazoesters are described. The reaction could be performed without rare metal catalysts, excess substrate, or the need for the slow addition of the diazoesters. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.115
• 作为产物：
  描述：

  乙烯基氨基甲酸苄酯 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以60%的产率得到benzyl methyl(vinyl)carbamate
  参考文献：
  名称：

  Highly Enantioselective Synthesis of Cyclopropylamine Derivatives via Ru(II)-Pheox-Catalyzed Direct Asymmetric Cyclopropanation of Vinylcarbamates

  摘要：

  The Ru(II)-Pheox-catalyzed asymmetric cyclopropanation of vinylcarbamates with diazoesters resulted in the corresponding cyclopropylamine derivatives in high yield and excellent diastereoselectivity (up to 96:4) and enantioselectivity (up to 99% ee).

  DOI：

  10.1021/ol303404c

文献信息

• Highly enantioselective synthesis of trifluoromethyl cyclopropanes by using Ru(<scp>ii</scp>)–Pheox catalysts
  作者：Manato Kotozaki、Soda Chanthamath、Takuji Fujii、Kazutaka Shibatomi、Seiji Iwasa

  DOI：10.1039/c8cc02286k

  日期：——

  vinyl amines, vinyl carbamates and dienes, was achieved by using Ru(II)–Pheox catalysts. This catalytic system can function at a low catalyst loading (3 mol%) compared with those reported previously, and the desired cyclopropane products are obtained in high yields with excellent diastereoselectivity (up to >99 : 1) and enantioselectivity (up to 97% ee).

  使用Ru（II）-Pheox催化剂可从烯烃（如乙烯基二茂铁，乙烯基醚，乙烯基胺，氨基甲酸乙烯基酯和二烯）不对称合成各种三氟甲基环丙烷。与以前报道的催化剂相比，该催化体系可以在较低的催化剂负载量（3 mol％）下运行，并以高收率获得了所需的环丙烷产物，具有优异的非对映选择性（高达> 99：1）和对映选择性（高达97％ee） ）。
• Visible-light-promoted and photocatalyst-free trifluoromethylation of enamides
  作者：Hao Wang、Yuanzheng Cheng、Shouyun Yu

  DOI：10.1007/s11426-015-5528-1

  日期：2016.2

  An efficient and practical method is developed for the trifluoromethylation of enamides using Umemoto’s reagent as the trifluoromethylating reagent. These reactions proceeded under visible light irradiation without any photocatalyst at room temperature in good chemical yields.

  开发了一种有效且实用的方法，用于使用梅本试剂作为三氟甲基化试剂进行酰胺的三氟甲基化。这些反应在室温下在无任何光催化剂的情况下在可见光照射下进行，化学收率良好。
• Indol-2-one Intermediates:  Mechanistic Evidence and Synthetic Utility. Total Syntheses of (±)-Flustramines A and C
  作者：James R. Fuchs、Raymond L. Funk

  DOI：10.1021/ol047532v

  日期：2005.2.1

  A variety of 3,3-disubstituted 2-indolinones have been prepared by treatment of 3-bromo-3-alkyl-2-indolinones with dienophiles/nucleophiles in the presence of cesium carbonate. Application of this general strategy has facilitated the total syntheses of the reverse prenylated marine natural products (+/-)-flustramine A and (+/-)-flustramine C. [Structure: see text]

  通过在碳酸铯存在下用亲二烯体/亲核试剂处理3-溴-3-烷基-2-吲哚酮制备了各种3，3-二取代的2-吲哚酮。该通用策略的应用促进了反向异戊酸酯化的海洋天然产物（+/-）-氟链胺A和（+/-）-氟链胺C的总合成。[结构：参见文本]
• Brønsted acid catalyzed proto-functionalization of enecarbamates and enamides: A convenient route to N,O-acetals
  作者：Ma Xiao-Yan、Zhang Chang-Fei、Hu Xinjun、Zou Wei、Li Yanli

  DOI：10.1016/j.tet.2020.131085

  日期：2020.4

  N,O-acetals are important structures found in many bioactive natural products, and this unique organic functional group can serve as a useful synthetic precursor to the unstable N-acylimines. In this paper, a convenient route to synthesize N-carbamoyl-N,O-acetals and N-acyl-N,O-acetals from enecarbamates and enamides in the presence of alcohols as the solvents and nucleophile sources under Brønsted

  N，O-乙缩醛是在许多具有生物活性的天然产物中发现的重要结构，并且这种独特的有机官能团可以用作不稳定的N-酰基酰亚胺的有用合成前体。在本文中，一个方便的途径来合成Ñ氨基甲酰基N，O -acetals和Ñ -acyl- N，O报道从醇作为布朗斯台德酸的条件下的溶剂和亲核试剂的来源的存在enecarbamates和烯酰胺-acetals。该策略可用于由一系列的氨基甲酸酯和酰胺与轻质醇制备各种N，O-乙缩醛，且收率高（52-98％）。
• Catalytic Enantioselective and Diastereoselective Addition of Aldehyde-Derived Enecarbamates to α-Oxo Aldehydes
  作者：Ryosuke Matsubara、Nobuyuki Kawai、Shū Kobayashi

  DOI：10.1002/anie.200600471

  日期：2006.6.2