N-(3-羟基苯基)氨基甲酸丙-2-烯基酯 | 73623-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3-羟基苯基)氨基甲酸丙-2-烯基酯
• 英文名称: prop-2-enyl N-(3-hydroxyphenyl)carbamate
• CAS: 73623-17-3
• 化学式: C₁₀H₁₁NO₃
• mdl: MFCD01739436
• 分子量: 193.202
• InChiKey: ICDBJWGDHSNFJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 五甲基苯 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以93%的产率得到N-(3-羟基苯基)氨基甲酸丙-2-烯基酯
  参考文献：
  名称：

  Mild Debenzylation of Aryl Benzyl Ether with BCl₃ in the Presence of Pentamethylbenzene as a Non-Lewis-Basic Cation Scavenger

  摘要：

  Scope and limitations of the debenzylation conditions for aryl benzyl ether, which was developed during our synthetic studies on yatakemycin, were investigated. The chemoselective debenzylation proceeds at low temperature with a combination of BCl(3) and pentamethylbenzene as a cation scavenger in the presence of various functional groups.

  DOI：

  10.1055/s-2008-1077980

文献信息

• Efficient Enzymatic Synthesis of Carbamates in Water Using Promiscuous Esterases/Acyltransferases
  作者：Hannes Meinert、Florian Oehlschläger、Clemens Cziegler、Jan Rockstroh、Irene Marzuoli、Serena Bisagni、Michael Lalk、Thomas Bayer、Hans Iding、Uwe T. Bornscheuer

  DOI：10.1002/anie.202405152

  日期：2024.7.22

  Biocatalysis provides an attractive approach to facilitate synthetic reactions in aqueous media. Motivated by the discovery of promiscuous aminolysis activity of esterases, we exploited the esterase from Pyrobaculum calidifontis VA1 (PestE) for the synthesis of carbamates from different aliphatic, aromatic, and arylaliphatic amines and a set of carbonates such as dimethyl‐, dibenzyl‐, or diallyl carbonate. Thus, aniline and benzylamine derivatives, aliphatic and even secondary amines could be efficiently converted into the corresponding benzyloxycarbonyl (Cbz)‐ or allyloxycarbonyl (Alloc)‐protected products in bulk water, with (isolated) yields of up to 99 %.