1-(3,6-dihydro-2H-thiopyran-4-yl)-1,3-dihydro-2H-benzimidazol-2-one | 61607-79-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(3,6-dihydro-2H-thiopyran-4-yl)-1,3-dihydro-2H-benzimidazol-2-one
• 英文别名: 1-(3,6-dihydro-2H-thiopyran-4-yl)-1,3-dihydro-benzoimidazol-2-one；2H-Benzimidazol-2-one, 1-(3,6-dihydro-2H-thiopyran-4-yl)-1,3-dihydro-；3-(3,6-dihydro-2H-thiopyran-4-yl)-1H-benzimidazol-2-one
• CAS: 61607-79-2
• 化学式: C₁₂H₁₂N₂OS
• 分子量: 232.306
• InChiKey: VBOIRBUBHJYAQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  四氢-4-氧代-2H-噻喃-3-甲酸甲酯 、 邻苯二胺 以32%的产率得到
  参考文献：
  名称：

  EIDEN F.; SCHULTE E., ARCH. PHARM. , 1976, 309, NO 8, 675-678

  摘要：

  DOI：

文献信息

• Rearrangement of spiro-benzimidazolines: preparation of N-alkenyl- and N-alkyl-benzimidazol-2-ones
  作者：Jeffrey T. Kuethe、Jack Varon、Karla G. Childers

  DOI：10.1016/j.tet.2007.06.106

  日期：2007.11

  A synthetically useful protocol has been developed for the preparation of highly functionalized N-alkenyl-benzimidazol-2-ones. Reaction of commercially available o-phenylenediamines with variously substituted cyclic ketones provides spiro-benzimidazolines. Treatment of these spiro-benzimidazolines with triphosgene in the presence of potassium carbonate results in rapid rearrangement and formation of N-alkenyl-benzimidazol-2-ones in modest to excellent yield for the two-step sequence. Extension of this methodology toward the preparation of a m opiate receptor antagonist and droperidol, a potent antiemetic and antipsychotic agent, currently a marketed pharmaceutical is also described. Upon treatment of spiro-benzimidazolines with triphosgene in the presence of sodium triacetoxyborohydride, N-alkyl-benzimidazol-2-ones were formed. (C) 2007 Merck & Co., Inc. Published by Elsevier Ltd. All rights reserved.
• EIDEN F.; SCHULTE E., ARCH. PHARM. <APBD-AJ>, 1976, 309, NO 8, 675-678
  作者：EIDEN F.、 SCHULTE E.

  DOI：——

  日期：——