1-(2-羟乙基)-3-(4-甲氧基苯基)硫脲 | 1848-60-8

• 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: 1-(2-羟乙基)-3-(4-甲氧基苯基)硫脲
• 英文名称: 1-(2-hydroxyethyl)-3-(4-methoxyphenyl)thiourea
• 英文别名: 1-(2-hydroxy-ethyl)-3-(4-methoxy-phenyl)-thiourea
• CAS: 1848-60-8
• 化学式: C₁₀H₁₄N₂O₂S
• mdl: MFCD00126022
• 分子量: 226.299
• InChiKey: KGDNJJRUJMQSLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-羟乙基)-3-(4-甲氧基苯基)硫脲 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以88%的产率得到1-(4-methoxyphenyl)imidazoline-2-thione
  参考文献：
  名称：

  Zade, Mangesh N.; Katiya, Manish M.; Deotale, Vinod D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2018, p. 1493 - 1500

  摘要：

  DOI：
• 作为产物：
  描述：

  C.I.酸性橙108 、 4-甲氧基苯基 异硫氰酸酯 以 丙酮 为溶剂， 反应 1.5h， 以88%的产率得到1-(2-羟乙基)-3-(4-甲氧基苯基)硫脲
  参考文献：
  名称：

  Synthesis of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas and evaluation as modulators of the isoforms of nitric oxide synthase

  摘要：

  Inhibition of the isoforms of nitric oxide synthase (NOS) has important applications in therapy of several diseases, including cancer. Using 1400W [N-(3-aminomethylbenzyl)acetamidme], thiocitrulline and N-delta-(4,5-dihydrothiazol-2-yl)ornithine as lead compounds, series of N-benzyl- and N-phenyl-2-amino-4,5-dihydrothiazoles and thioureas were designed as inhibitors of NOS. Ring-substituted benzyl and phenyl isothiocyanates were synthesised by condensation of the corresponding amines with thiophosgene and addition of ammonia gave the corresponding thioureas in high yields. The substituted 2-amino-4,5-dihydrothiazoles were approached by two routes. Treatment of simple benzylamines with 2-methylthio-4,5-dihydrothiazole at 180degreesC afforded the corresponding 2-benzylamino-4,5-dihydrothiazoles. For less nucleophilic amines and those carrying more thermally labile substituents, the 4,5-dihydrothiazoles were approached by acid-catalysed cyclisation of N-(2-hydroxyethyl)thioureas. This cyclisation was shown to proceed by an S(N)2-like process. Modest inhibitory activity was shown by most of the thioureas and 4,5-dihydrothiazoles, with N-(3-aminomethylphenyl)thiourea (IC50 = 13 muM vs rat neuronal NOS and IC50 = 23 muM vs rat inducible NOS) and 2-(3-aminomethylphenylamino)-4,5-dihydrothiazole (IC50 - 13 muM vs rat neuronal NOS and IC50 = 19 muM vs human inducible NOS) being the most potent. Several thioureas and 4,5-dihydrothiazoles were found to stimulate the activity of human inducible NOS in a time-dependent manner. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00451-6

文献信息

• Amine-Catalyzed Phospha-Michael Reaction of α,β-Unsaturated Aldehydes and Ketones with Multifunctional <i>N</i>-Heterocyclic Phosphine-Thioureas as Phosphonylation Reagent
  作者：Hai Huang、Jun Yong Kang

  DOI：10.1021/acs.orglett.6b02121

  日期：2016.9.2

  amine-catalyzed phospha-Michael addition reaction of α,β-unsaturated aldehydes/ketones with N-heterocyclic phosphines for the synthesis of γ-ketodiazaphosphonates has been developed. With freedom from nucleophile additives, this mild process affords a range of structurally diverse γ-ketodiazaphosphonates in moderate to excellent yields. Importantly, various α,β-unsaturated ketones were also tolerated in this

  已经开发出一种有效的胺催化的α，β-不饱和醛/酮与N-杂环膦的胺-迈克尔-迈克尔加成反应，用于合成γ-酮二氮膦酸酯。由于没有亲核添加剂，这种温和的方法以中等到极好的收率提供了一系列结构多样的γ-酮重氮膦酸酯。重要的是，在此过程中还可以耐受各种α，β-不饱和酮，并具有中等收率。
• N-Heterocyclic Phosphines
  申请人：The Board of Regents of the Nevada System of Higher Education on Behalf of the Unive. of Nevada

  公开号：US20180118770A1

  公开（公告）日：2018-05-03

  Provided herein are N-heterocyclic phosphines (NHPs) useful in metal-free phosphorus-carbon bond forming reactions. Methods for preparing vinylphosphonates using NHPs also are provided. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本文提供了一种在无金属条件下进行磷-碳键形成反应中有用的N-杂环膦（NHPs）。还提供了使用NHPs制备乙烯磷酸酯的方法。本摘要旨在作为在特定领域搜索的扫描工具，不限制本发明。
• Regioselective Synthesis of α- and <i>γ-</i>Amino Quinolinyl Phosphonamides Using <i>N</i>-Heterocyclic Phosphines (NHPs)
  作者：Manasa Shetty、Hai Huang、Jun Yong Kang

  DOI：10.1021/acs.orglett.7b03829

  日期：2018.2.2

  phosphonylation of quinolines for the synthesis of α-amino quinolinyl phosphonamides and γ-amino quinolinyl phosphonamides has been developed under mild reaction conditions. An NHP-thiourea enables selective synthesis of α-amino quinolinyl phosphonamides by a Reissert-type reaction, and an NHP-tosylamide affords γ-amino quinolinyl phosphonamides via a 1,4-conjugate addition reaction. The corresponding amino

  在温和的反应条件下，已开发出用于合成α-氨基喹啉基膦酰胺和γ-氨基喹啉基膦酰胺的喹啉的区域选择性膦酰基化。NHP-硫脲能够通过Reissert型反应选择性合成α-氨基喹啉基膦酰胺，而NHP-甲苯磺酰胺则通过1,4-共轭加成反应提供γ-氨基喹啉基膦酰胺。以中等至优异的产率（高达99％的产率）和区域选择性（高达99：1）和良好的官能团耐受性获得了相应的氨基喹啉基膦酸酯加合物。
• A Reagent-Controlled Phospha-Michael Addition Reaction of Nitroalkenes with Bifunctional N-Heterocyclic Phosphine (NHP)-Thioureas
  作者：Hai Huang、Jake Palmas、Jun Yong Kang

  DOI：10.1021/acs.joc.6b02490

  日期：2016.12.2

  phospha-Michael addition reaction of nitroalkenes to afford diversely substituted β-nitrodiazaphosphonates. This transformation takes place at room temperature under catalyst-free conditions and exhibits broad functional group tolerance. The key to success in catalyst, additive-free reaction conditions is the suitable hydrogen-bond activation of the nitro group by a Brønsted acid (thiourea), which

  双功能N-杂环膦（NHP）-硫脲已成功用于硝基烯烃的Pha-Michael加成反应，以提供不同取代的β-硝基二氮杂膦酸酯。该转变在室温下在无催化剂的条件下进行，并表现出宽泛的官能团耐受性。催化剂成功，无添加剂反应条件成功的关键是布朗斯台德酸（硫脲）对硝基进行的氢键适当活化，该反应巧妙地与高度亲核的NHP基序结合，产生协同作用。重要的是，这种转化使得能够进行药学上，生物学上重要的β-氨基膦酸的两步合成。
• Utility of Bifunctional <i>N</i>-Heterocyclic Phosphine (NHP)-Thioureas for Metal-Free Carbon–Phosphorus Bond Construction toward Regio- and Stereoselective Formation of Vinylphosphonates
  作者：Karimulla Mulla、Kyle L. Aleshire、Paul M. Forster、Jun Yong Kang

  DOI：10.1021/acs.joc.5b02184

  日期：2016.1.4

  practical protocol for completely regioselective and highly stereoselective synthesis of vinyldiazaphosphonates from N-heterocyclic phosphine (NHP) and allenes via phospha-Michael/intramolecular nucleophilic substitution reaction has been developed. This transformation enabled the synthesis of valuable densely functionalized vinyldiazaphosphonates with a β-, γ-unsaturated ester moiety under mild reaction

  已经开发了一种有效和实用的方案，用于通过膦-迈克尔/分子内亲核取代反应，从N-杂环膦（NHP）和丙二烯完全区域选择性和高度立体选择性地合成乙烯基二氮杂膦酸酯。该转化使得能够在温和的反应条件下合成具有β-，γ-不饱和酯部分的有价值的稠密官能化的乙烯基二氮杂膦酸酯。通过一系列合成操作证明了乙烯基二氮杂膦酸酯的合成效用。