O-(2-carbomethoxyphenyl) N,N-dimethylthiocarbamate | 13522-58-2

• 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: O-(2-carbomethoxyphenyl) N,N-dimethylthiocarbamate
• 英文别名: methyl 2-((dimethylcarbamothioyl)oxy)benzoate；2--benzoesaeure-methylester；Methyl 2-[(dimethylcarbamothioyl)oxy]benzoate；methyl 2-(dimethylcarbamothioyloxy)benzoate
• CAS: 13522-58-2
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: HEXHFSWVDUAPEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  322.3±44.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  70.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-(2-carbomethoxyphenyl) N,N-dimethylthiocarbamate 在 盐酸羟胺 作用下， 生成 Methyl 2-{[2-(2,5-dichloro-3-thienyl)-2-(hydroxyimino)ethyl]sulfanyl}benzenecarboxylate
  参考文献：
  名称：

  Ago-allosteric modulators of human glucagon-like peptide 2 receptor

  摘要：

  Glucagon-like peptide 2 (GLP-2) is an intestinotropic peptide that binds to GLP-2 receptor (GLP-2R), a class-B G protein-coupled receptor (GPCR). Few synthetic agonists have been reported so far for class-B GPCRs. Here, we report the first scaffold compounds of ago-allosteric modulators for human GLP-2R, derived from methyl 2-{[(2Z)-2-(2,5-dichlorothiophen-3-yl)-2-(hydroxyimino) ethyl] sulfanyl}benzoate (compound 1). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.026
• 作为产物：
  描述：

  二甲氨基硫代甲酰氯 、 水杨酸甲酯 在 potassium fluoride on basic alumina 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以83%的产率得到O-(2-carbomethoxyphenyl) N,N-dimethylthiocarbamate
  参考文献：
  名称：

  Potassium Fluoride on Alumina: Synthesis of O-Aryl N,N-Dimethylthiocarbamates and their Rearrangement into S-Aryl N,N-Dimethyl-Thiocarbamates Under Microwave Irradiation

  摘要：

  A series of O-aryl N,N-dimethyl thiocarbamates have been prepared by the reaction of dimethylthiocarbamoyl chloride with phenols absorbed on potassium fluoride on alumina. The rearrangement of O-aryl N,N-dimethylthiocarbamate into S-aryl N,N-dimethyl thiocarbamate under microwave irradiation was also studied. The use of conductive support like graphite or silicon carbide allow these rearrangements although the O-aryl N,N-dimethylthiocarbamates have very low dielectric lost.

  DOI：

  10.1080/00397919608004558

文献信息

• Intramolecular interception of the Newman-Kwart rearrangement by carboxylic acids
  作者：Timothy A. Ablott、Mitchell G. Fishburn、David R. Turner、Christopher Richardson

  DOI：10.1016/j.tetlet.2020.152153

  日期：2020.7

  Instead of undergoing the Newman-Kwart rearrangement, thermally-promoted reactions of O-aryl dimethylthiocarbamates featuring ortho-carboxylic acid substituents result in the loss of carbonylsulfide and formation of N,N-dimethylsalicylamides in high yields.

  代替经历Newman-Kwart重排，具有邻羧酸取代基的O-芳基二甲基硫代氨基甲酸酯的热促进反应导致羰基硫的损失和高产率的N，N-二甲基水杨酰胺的形成。
• The Conversion of Phenols to Thiophenols via Dialkylthiocarbamates¹
  作者：Melvin S. Newman、Harold A. Karnes

  DOI：10.1021/jo01350a023

  日期：1966.12
• [EN] VITAMIN D-DERIVATIVES AND THEIR USE IN TREATING OSTEOPOROSIS AND RELATED BONE DISORDERS<br/>[FR] DERIVES DE VITAMINE D ET LEUR UTILISATION DANS LE CADRE DU TRAITEMENT DE L'OSTEOPOROSE ET DES TROUBLES OSSEUX ASSOCIES
  申请人：LEO PHARM PROD LTD

  公开号：WO2001056982A1

  公开（公告）日：2001-08-09

  The invention relates to compounds of the formula (I) wherein R1 et R2, which may be the same or different, represent hydrogen or a residue after removal of 1 hydrogen atom from a straight, branched or cyclic, saturated or unsaturated, C¿1?-C6-hydrocarbon; or R?1 and R2¿, taken together with the carbon atom to which they are attached (marked with an asterisk in formula (I), can form a C¿3?-C8 carbocyclic ring; Q represents a diradical residue after removal of 2 hydrogen atoms from a straight, branched or cyclic, saturated or unsaturated C1-C8-hydrocarbon substituted with one or more chlorine or bromine atoms and/or substituted with one or more alkyl or alkoxy groups; R?1, R2¿ and/or Q is optionally substituted with one or more fluorine atoms; m is 0, 1 or 2 and n is 0 or 1.
• 10.1016/j.jhazmat.2024.134705
  作者：Wu, Huihui、Wu, Aihong、Liu, Liqiang、Kuang, Hua、Sun, Maozhong、Xu, Chuanlai、Xu, Xinxin

  DOI：10.1016/j.jhazmat.2024.134705

  日期：——
• Potassium Fluoride on Alumina: Synthesis of O-Aryl N,N-Dimethylthiocarbamates and their Rearrangement into S-Aryl N,N-Dimethyl-Thiocarbamates Under Microwave Irradiation
  作者：Didier Villemin、Messaoud Hachemi、Mekki Lalaoui

  DOI：10.1080/00397919608004558

  日期：1996.7

  A series of O-aryl N,N-dimethyl thiocarbamates have been prepared by the reaction of dimethylthiocarbamoyl chloride with phenols absorbed on potassium fluoride on alumina. The rearrangement of O-aryl N,N-dimethylthiocarbamate into S-aryl N,N-dimethyl thiocarbamate under microwave irradiation was also studied. The use of conductive support like graphite or silicon carbide allow these rearrangements although the O-aryl N,N-dimethylthiocarbamates have very low dielectric lost.