1,3-dihydrospiro[2H-benzimidazole-2,4'-piperidine]-1'-carboxylic acid ethyl ester | 959700-75-5

• 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-dihydrospiro[2H-benzimidazole-2,4'-piperidine]-1'-carboxylic acid ethyl ester
• 英文别名: Ethyl spiro[1,3-dihydrobenzimidazole-2,4'-piperidine]-1'-carboxylate；ethyl spiro[1,3-dihydrobenzimidazole-2,4'-piperidine]-1'-carboxylate
• CAS: 959700-75-5
• 化学式: C₁₄H₁₉N₃O₂
• 分子量: 261.324
• InChiKey: UWXUMPJPMBBKSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dihydrospiro[2H-benzimidazole-2,4'-piperidine]-1'-carboxylic acid ethyl ester 、 三光气 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到4-(2,3-二氢-2-氧代-1H-苯并咪唑-1-基)-3,6-二氢-2H-吡啶-1-羧酸乙酯
  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：

  邻苯二胺 、 N-乙氧羰基-4-哌啶酮 以 醋酸异丙酯 为溶剂， 反应 2.0h， 以64%的产率得到1,3-dihydrospiro[2H-benzimidazole-2,4'-piperidine]-1'-carboxylic acid ethyl ester
  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

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.