1-(2-chloro-6-methylphenyl)-(1,2-dideoxy-α-D-glucofurano)[2,1-d]imidazolidine-2-thione | 258879-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-(2-chloro-6-methylphenyl)-(1,2-dideoxy-α-D-glucofurano)[2,1-d]imidazolidine-2-thione
• 英文别名: (3aS,5S,6R,6aR)-3-(2-chloro-6-methylphenyl)-5-[(1R)-1,2-dihydroxyethyl]-6-hydroxy-3a,5,6,6a-tetrahydro-1H-furo[2,3-d]imidazole-2-thione
• CAS: 258879-37-7
• 化学式: C₁₄H₁₇ClN₂O₄S
• 分子量: 344.819
• InChiKey: QFFQUGFWTHQNMY-HFULGKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-chloro-6-methylphenyl)-(1,2-dideoxy-α-D-glucofurano)[2,1-d]imidazolidine-2-thione 、 alkaline earth salt of/the/ methylsulfuric acid 以85%的产率得到[(2R)-2-[(3aS,5S,6R,6aR)-6-acetyloxy-3-(2-chloro-6-methylphenyl)-2-sulfanylidene-3a,5,6,6a-tetrahydro-1H-furo[2,3-d]imidazol-5-yl]-2-acetyloxyethyl] acetate
  参考文献：
  名称：

  Atropisomeric carbohydrate imidazolidines: a novel class of nonbiaryl atropisomers

  摘要：

  Stable axially chiral atropisomers have been prepared by reaction of 2-aminosugars with o,o'-disubstituted aryl isocyanates and isothiocyanates; these rotationally restricted heterobiaryls constitute a novel class of atropisomers for use in atroposelective reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00428-0
• 作为产物：
  描述：

  异硫氰酸2-氯-6-甲基苯基酯 在 甲醇 、 氨 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 72.5h， 生成 1-(2-chloro-6-methylphenyl)-(1,2-dideoxy-α-D-glucofurano)[2,1-d]imidazolidine-2-thione
  参考文献：
  名称：

  Atropisomeric carbohydrate imidazolidines: a novel class of nonbiaryl atropisomers

  摘要：

  Stable axially chiral atropisomers have been prepared by reaction of 2-aminosugars with o,o'-disubstituted aryl isocyanates and isothiocyanates; these rotationally restricted heterobiaryls constitute a novel class of atropisomers for use in atroposelective reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00428-0

文献信息

• Non-biaryl atropisomers derived from carbohydrates. Part 3: Rotational isomerism of sterically hindered heteroaryl imidazolidine-2-ones and 2-thiones
  作者：Martín Ávalos、Reyes Babiano、Pedro Cintas、Michael B. Hursthouse、José L. Jiménez、Mark E. Light、Juan C. Palacios、Guadalupe Silvero

  DOI：10.1016/j.tet.2005.06.017

  日期：2005.8

  The present work describes in detail the preparation and structural characterization of a series of heteroaryls in which an o,o′-disubstituted phenyl ring is connected through a single C–N bond to a heterocyclic fragment of a chiral imidazolidine-2-one or 2-thione. As a consequence of hindered rotation, some of these substances exist as stable rotamers at room temperature and can easily be separated

  目前的工作中详细描述了一系列杂芳基的制备和结构表征，其中ø，ö '二取代的苯基环通过一个C-N键连接至手性咪唑烷-2-酮或2所述的杂环片段-硫酮。由于旋转受阻，这些物质中的一些在室温下以稳定的旋转异构体形式存在，并且可以轻松进行分离和表征。还进行了分子力学计算以评估旋转障碍。