1,2',3,3',5',6'-Hexahydrospiro[benzimidazole-2,4'-pyran] | 959700-85-7

• 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: 1,2',3,3',5',6'-Hexahydrospiro[benzimidazole-2,4'-pyran]
• 英文别名: spiro[1,3-dihydrobenzimidazole-2,4'-oxane]
• CAS: 959700-85-7
• 化学式: C₁₁H₁₄N₂O
• mdl: MFCD24604239
• 分子量: 190.245
• InChiKey: KSQYDMDMXBGQNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  33.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2',3,3',5',6'-Hexahydrospiro[benzimidazole-2,4'-pyran] 、 三光气 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到1-(3,6-dihydro-2H-pyran-4-yl)-1,3-dihydro-2H-benzimidazol-2-one
  参考文献：
  名称：

  Rearrangement of spiro-benzimidazolines: preparation of N-alkenyl- and N-alkyl-benzimidazol-2-ones

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.06.106
• 作为产物：
  描述：

  四氢吡喃酮 、 邻苯二胺 以 醋酸异丙酯 为溶剂， 反应 2.0h， 以58%的产率得到1,2',3,3',5',6'-Hexahydrospiro[benzimidazole-2,4'-pyran]
  参考文献：
  名称：

  Rearrangement of spiro-benzimidazolines: preparation of N-alkenyl- and N-alkyl-benzimidazol-2-ones

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.06.106