(s)-(9ci)-alpha-(1-甲基乙基)-1H-苯并咪唑-2-甲胺 | 59653-66-6

• 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: (s)-(9ci)-alpha-(1-甲基乙基)-1H-苯并咪唑-2-甲胺
• 中文别名: （S）-（-）-2-（α-（异丙基甲酰胺）-1H-苯并咪唑；(S)-(-)-2-(Α-(I-丙基)甲胺)-1H-苯并咪唑
• 英文名称: (S)-(-)-2-(α-(i-propyl)methanamine)-1H-benzimidazole
• 英文别名: (S)-1-(1H-benzo[d]imidazol-2-yl)-2-methylpropan-1-amine；(1'S)-1'-amino-1'-isopropyl-1'-(benzimidazo-2-yl)methane；(1S)-1-(1H-benzimidazol-2-yl)-2-methylpropan-1-amine
• CAS: 59653-66-6
• 化学式: C₁₁H₁₅N₃
• mdl: MFCD09863530
• 分子量: 189.26
• InChiKey: JDPVJORLNSVLOK-JTQLQIEISA-N

物化性质

• 熔点：
  166-168°C
• 比旋光度：
  -29.9° (c 1.0 CHCl3)
• 沸点：
  375.3±25.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (s)-(9ci)-alpha-(1-甲基乙基)-1H-苯并咪唑-2-甲胺 、 间苯二异氰酸酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以0.094 g的产率得到1-[(1S)-1-(1H-benzimidazol-2-yl)-2-methylpropyl]-3-[3-[[(1S)-1-(1H-benzimidazol-2-yl)-2-methylpropyl]carbamoylamino]phenyl]urea
  参考文献：
  名称：

  l-Valine derived benzimidazole based bis-urea in enantioselective fluorescence sensing of L-tartrate

  摘要：

  L-Valine derived benzimidazole based bis-urea 1 has been designed and synthesized. The bis-urea 1 is found to act as enantioselective chemosensor for tartrate. The sensor shows greater fluorescence response for L-tartrate in DMSO. The enantiomeric fluorescence difference ratio (ef) has been determined to be 2.46. In comparison, less steric receptor 2 exhibits a marginal preference for D-tartrate over the L-tartrate in DMSO and validates the steric role of the substituents around the benzimidazole motif in 1 toward enantioselective recognition of tartrate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.087
• 作为产物：
  描述：

  (S)-tert-butyl 1-(2-aminophenylamino)-3-methyl-1-oxobutan-2-ylcarbamate 在 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (s)-(9ci)-alpha-(1-甲基乙基)-1H-苯并咪唑-2-甲胺
  参考文献：
  名称：

  l-Valine derived benzimidazole based bis-urea in enantioselective fluorescence sensing of L-tartrate

  摘要：

  L-Valine derived benzimidazole based bis-urea 1 has been designed and synthesized. The bis-urea 1 is found to act as enantioselective chemosensor for tartrate. The sensor shows greater fluorescence response for L-tartrate in DMSO. The enantiomeric fluorescence difference ratio (ef) has been determined to be 2.46. In comparison, less steric receptor 2 exhibits a marginal preference for D-tartrate over the L-tartrate in DMSO and validates the steric role of the substituents around the benzimidazole motif in 1 toward enantioselective recognition of tartrate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.087
• 作为试剂：
  描述：

  6-溴-3-硝基-2-苯基-2H-1-苯并吡喃 、 丙酸,3-(苯基氨基)-3-硫代-,乙基酯 在 三乙烯二胺 、 tris-(dibenzylideneacetone)dipalladium(0) 、 (s)-(9ci)-alpha-(1-甲基乙基)-1H-苯并咪唑-2-甲胺 、 2-(二叔丁基膦)联苯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  一种具有抗菌活性的硅烷偶联剂及其制备方法

  摘要：

  本发明公开一种具有抗菌活性的硅烷偶联剂及其制备方法；该具有抗菌活性的硅烷偶联剂由硫代酰胺乙酸乙酯与不同取代基取代的3‑硝基苯并吡喃先发生麦克加成，接着分子内发生加成并关环反应，所得到的2‑芳基苯并吡喃并二氢噻吩衍生物再与硅氧烷发生取代反应生成具有抗菌活性的硅烷偶联剂；本发明得到的具有抗菌活性的硅烷偶联剂含有大量的苯环，分子具有很强的刚性，且分子链中含有卤素，具有阻燃性能，应用于复合材料不仅可以使复合材料具有抗菌性，还可以增强材料的刚性和阻燃性。

  公开号：

  CN111606922A

文献信息

• A Novel Dual Organocatalyst for the Asymmetric Pinder Reaction and a Mechanistic Proposal Consistent with the Isoinversion Effect Thereof
  作者：Fotini Moschona、Athena Vagena、Veroniki P. Vidali、Gerasimos Rassias

  DOI：10.3390/molecules26216398

  日期：——

  and enantioselectivity. To the best of our knowledge, there has been only one attempt prior to this work towards the development of a catalytic enantioselective Pinder reaction. In our approach, we designed, synthesized, and tested dual chiral organocatalysts by combining BIMAH amines, (2-(α-(alkyl)methanamine)-1H-benzimidazoles, and a Lewis acid motif, such as squaramides, ureas and thioureas. The

  一般而言，Pinder 反应涉及可烯醇化酸酐和醛之间的反应，该反应首先通过 Knoevenagel 反应进行，然后进行闭环过程，生成具有至少两个手性中心的内酯。这些支架经常存在于天然产物和合成生物活性分子中，因此引起了有机合成和药物化学的浓厚兴趣，特别是在控制非对映选择性和对映选择性方面。据我们所知，在这项工作之前，只有一次尝试开发催化对映选择性 Pinder 反应。在我们的方法中，我们通过结合 BIMAH 胺、(2-(α-(烷基)甲胺)-1H-苯并咪唑和路易斯酸基序，如方酰胺、脲和硫脲，设计、合成和测试了双手性有机催化剂。最佳催化剂是带有双(3,5-三氟甲基)硫脲的异丙基BIMAH衍生物，它可以从各种芳香醛中得到Pinder产物，其非对映异构体比例>98:2，对映选择性高达92 ee%。有趣的是，这种对映选择性催化过程在较高浓度下增加，并表现出同向转化效应，即相对于温度的倒“U”形依赖性
• α-Amino Acid Derived Benzimidazole-Linked Rhodamines: A Case of Substitution Effect at the Amino Acid Site toward Spiro Ring Opening for Selective Sensing of Al³⁺ Ions
  作者：Anupam Majumdar、Subhendu Mondal、Constantin G. Daniliuc、Debashis Sahu、Bishwajit Ganguly、Sourav Ghosh、Utpal Ghosh、Kumaresh Ghosh

  DOI：10.1021/acs.inorgchem.7b00835

  日期：2017.8.7

  changes. In contrast, glycine-derived benzimidazole 3 remains silent in the recognition event and emphasizes the role of α-substitution of amino acid undertaken in the design. The fact has been addressed on the basis of the single-crystal X-ray structures and theoretical calculations. Moreover, pink 1·Al3+ and 2·Al3+ ensembles selectively sensed F– ions over other halides through a discharge of color. Importantly

  α -氨基酸衍生的苯并咪唑联罗丹明已被合成，和它们的金属离子传感特性进行了评价。实验上，衍生自1-缬氨酸和1-苯基甘氨酸的基于苯并咪唑的若丹明1和2可选择性识别CH 3 CN水溶液中的Al 3+离子（CH 3 CN / H 2 O 4/1 v / v，10 mM tris HCl缓冲液（pH 7.0），通过显示颜色和“开启”发射变化来实现。相反，甘氨酸衍生的苯并咪唑3在识别事件中保持沉默，并强调了氨基酸α-取代在设计中所起的作用。该事实已根据单晶X射线结构和理论计算得到解决。此外，粉1 ·的Al 3+和2 ·铝3+合奏选择性地感测˚F -通过颜色的放电过其它卤化物离子。重要的是，化合物1和2是可渗透细胞的，并且已用作成像试剂，用于检测人肺癌细胞系A549中的Al 3+摄取。
• Hybrid NH₂-Benzimidazole Ligands for Efficient Ru-Catalyzed Asymmetric Hydrogenation of Aryl Ketones
  作者：Yuehui Li、Kuiling Ding、Christian A. Sandoval

  DOI：10.1021/ol802766u

  日期：2009.2.19

  Readily available hybrid NH2/benzimidazole ligands (R-bimaH, 1) dramatically influence the outcome of established Ru-based catalysts during asymmetric hydrogenation of aryl ketones. The benzimidazole functionality results in reversal of the typically observed chiral induction and allows for hydrogenation to be uncharacteristically conducted in nonprotic solvents. The developed systems efficiently catalyzed the AH of a number of ketones in up to 99% ee.
• Design, synthesis and antibacterial activity of novel actinonin derivatives containing benzimidazole heterocycles
  作者：Datong Zhang、Zongheng Wang、Weiren Xu、Fanggang Sun、Lida Tang、Jianwu Wang

  DOI：10.1016/j.ejmech.2008.05.009

  日期：2009.5

  A series of novel actinonin derivatives containing a benzimidazole heterocycle linked as amide isostere have been designed and synthesized. The structures of all the synthesized compounds were confirmed by analytical and spectroscopic methods. All the compounds were evaluated in vitro against Staphylococcus aureus, Klebsiella pneumoniae, and Sarcina lutea. Among them, compound la with unsubstituted benzimidazole ring exhibited potent antibacterial activities. (C) 2008 Elsevier Masson SAS. All rights reserved.
• <scp>l</scp>-Valine-derived simple benzimidazole-based host in selective sensing of Hg(II) ions
  作者：Kumaresh Ghosh、Tanmay Sarkar

  DOI：10.1080/10610278.2012.712696

  日期：2012.10

  A new and an easy-to-make simple benzimidazole-based chemosensor 1, derived from L-valine is reported. The chemosensor effectively recognises Hg2+ ion in the open cleft in CH3CN containing 0.2% DMSO by exhibiting significant enhancement in fluorescence emission. In the selectivity, the steric isopropyl groups in 1 play the key role as confirmed by considering the model compound 2. The ensemble of 1. Hg2+, on the other hand, shows the fluorescence sensing of L-cysteine, homocysteine, and glutathione over the other amino acids with no thiol group in aq. DMSO (DMSO:H2O 4:1, v/v).