(e)-(9ci)-2-(1-丙烯基)-1H-苯并咪唑 | 105259-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (e)-(9ci)-2-(1-丙烯基)-1H-苯并咪唑
• 英文名称: 2-[(1E)-prop-1-en-1-yl]-1H-benzimidazole
• 英文别名: (E)-2-(prop-1-en-1-yl)-1H-benzimidazole；2-(1-propenyl)benzimidazole；2-propenyl-1H-benzoimidazole；2-Propenyl-1H-benzimidazol；2-(1-Propenyl)-benzimidazol；2-Propenyl-benzimidazol；2-[(E)-prop-1-enyl]-1H-benzimidazole
• CAS: 105259-40-3
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: LGWRNIXKHGASPF-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (e)-(9ci)-2-(1-丙烯基)-1H-苯并咪唑 在 (S)-3,3'-双(9-蒽基)-1,1'-联萘-2,2'-二基磷酸氢酯 、 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 144.17h， 生成 (S)-2-(2-(pyrazol-1-yl)propyl)-1-tosylbenzoimidazole
  参考文献：
  名称：

  手性磷酸催化烯基苯并咪唑的对映选择性氮杂Michael型加成反应

  摘要：

  N-保护的烯基苯并咪唑与吡唑或吲唑作为氮亲核试剂之间的高度对映选择性Michael型加成（MTA）反应是使用手性磷酸催化剂首次完成的。理论研究阐明了反应途径和立体化学结果的起源，其中苯并咪唑的催化剂取代基和N-保护基团导致了较高的对映选择性。

  DOI：

  10.1002/anie.201508231
• 作为产物：
  描述：

  2-烯丙基-1H-苯并咪唑 生成 (e)-(9ci)-2-(1-丙烯基)-1H-苯并咪唑
  参考文献：
  名称：

  Reaction of imidazoles with allyltributyltin in the presence of chloroformate

  摘要：

  The reaction of imidazoles with allyltributyltin in the presence of chloroformate gave 2-allyl-1,3-dialkoxycarbonyl-4-imidazolines in good yields. The addition products were aromatized with potassium ferricyanide under basic condition lo afford corresponding 2-allylimidazoles.

  DOI：

  10.1016/s0040-4039(00)79104-0

文献信息

• Allylation of azoles with allyltributyltin via unstable N-(alkoxycarbonyl)azolium salts
  作者：Takashi Itoh、Hiroshi Hasegawa、Kazuhiro Nagata、Akio Ohsawa

  DOI：10.1021/jo00085a020

  日期：1994.3

  The one-pot reactions of imidazoles with allyltributyltin in the presence of alkyl chloroformates gave 2-allyl-1,3-bis(alkoxycarbonyl)-4-imidazolines in good yields. The reactions of thiazoles and oxazoles also proceeded in a similar manner. The instability of the intermediary quaternary salts required the nucleophiles to be added simultaneously with the chloroformate. Therefore, the reaction was specific for allyltributyltin, since it doesn't react with the carbonyl group of chloroformates. The dihydro allyl adducts thus obtained were aromatized with potassium ferricyanide under basic conditions to afford the corresponding 2-allylazoles.
• Ried; Stahlhofen, Chemische Berichte, 1957, vol. 90, p. 815,822
  作者：Ried、Stahlhofen

  DOI：——

  日期：——
• Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles
  作者：Yadaganahalli K. Bommegowda、Gejjalagere S. Lingaraju、Saji Thamas、Koravangala S. Vinay Kumar、Challanayakanahally S. Pradeepa Kumara、Kanchugarakoppal S. Rangappa、Marilinganadoddi P. Sadashiva

  DOI：10.1016/j.tetlet.2013.03.075

  日期：2013.5

  One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75-94%) was achieved within 60 min. Weinreb amide shows high selectivity in the reaction, even in presence of other active functional groups such as carboxyl, halogen, cyano, and methoxy. (c) 2013 Elsevier Ltd. All rights reserved.
• Novel N-ferrocenylmethyl, N′-methyl-2-substituted benzimidazolium iodide salts with in vitro activity against the P. falciparum malarial parasite strain NF54
  作者：Joshua Howarth、Keith Hanlon

  DOI：10.1016/s0040-4039(00)02106-7

  日期：2001.1

  Herein we disclose results of our research into a novel class of benzimidazolium compounds active against malarial parasites. We have discovered that N-ferrocenylmethyl, N'-methyl-2-aryl (or styryl) benzimidazolium iodide salts show excellent in vitro activity against the P. falciparum malarial parasite strain NF54. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Reaction of imidazoles with allyltributyltin in the presence of chloroformate
  作者：Takashi Itoh、Hiroshi Hasegawa、Kazuhiro Nagata、Mamiko Okada、Akio Ohsawa

  DOI：10.1016/s0040-4039(00)79104-0

  日期：1992.9

  The reaction of imidazoles with allyltributyltin in the presence of chloroformate gave 2-allyl-1,3-dialkoxycarbonyl-4-imidazolines in good yields. The addition products were aromatized with potassium ferricyanide under basic condition lo afford corresponding 2-allylimidazoles.