1-(2-ethyl-6-methylphenyl)-(1,2-dideoxy-α-D-glucofurano)[1,2-d]imidazolidine-2-thione | 258879-38-8

• 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-ethyl-6-methylphenyl)-(1,2-dideoxy-α-D-glucofurano)[1,2-d]imidazolidine-2-thione
• 英文别名: (3aS,5S,6R,6aR)-5-[(1R)-1,2-dihydroxyethyl]-3-(2-ethyl-6-methylphenyl)-6-hydroxy-3a,5,6,6a-tetrahydro-1H-furo[2,3-d]imidazole-2-thione
• CAS: 258879-38-8
• 化学式: C₁₆H₂₂N₂O₄S
• 分子量: 338.428
• InChiKey: DZBSUNYEVUDNAF-BBIZWXPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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-ethyl-6-methylphenyl)-(1,2-dideoxy-α-D-glucofurano)[1,2-d]imidazolidine-2-thione 、 alkaline earth salt of/the/ methylsulfuric acid 以65%的产率得到Acetic acid (3aS,5S,6R,6aR)-5-((R)-1,2-diacetoxy-ethyl)-3-(2-ethyl-6-methyl-phenyl)-2-thioxo-hexahydro-furo[2,3-d]imidazol-6-yl ester
  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：

  2-deoxy-2-amino glucose 在 碳酸氢钠 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 1-(2-ethyl-6-methylphenyl)-(1,2-dideoxy-α-D-glucofurano)[1,2-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 4: Absolute stereochemistry of carbohydrate-based imidazolidine-2-ones and 2-thiones with axial and central chirality
  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.2005.06.018

  日期：2005.8

  NMR spectroscopy has proven to be an enabling methodology in elucidating the axial chirality of a series of non-biaryl atropisomers attached to a carbohydrate moiety, based on deshielding effects caused by the aromatic ring.

  NMR光谱已被证明是一种基于由芳环引起的去屏蔽作用来阐明与碳水化合物部分连接的一系列非联芳基阻转异构体的轴向手性的可行方法。