(S)-2-(α-hydroxybenzyl)benzimidazole | 25161-52-8

• 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: (S)-2-(α-hydroxybenzyl)benzimidazole
• 英文别名: (S)-1H-benzimidazol-2-yl(phenyl)methanol
• CAS: 25161-52-8
• 化学式: C₁₄H₁₂N₂O
• 分子量: 224.262
• InChiKey: JEAWPIKEEQZLJQ-ZDUSSCGKSA-N

物化性质

• 熔点：
  83-84 °C
• 沸点：
  500.6±43.0 °C(Predicted)
• 密度：
  1.298±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(α-hydroxybenzyl)benzimidazole 在 copper(l) iodide 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  手性苯并咪唑衍生的双苯基三唑作为碘化物和手性胺的手性传感器

  摘要：

  使用点击化学，已经以高收率制备了一系列手性的2-羟乙基/苄基苯并咪唑基芳基三唑镊子。手性池策略已被用于以对映体富集的形式获得基于苯并咪唑的镊子。芳基三唑镊子S -（-）- 5a和S -（+）- 8a对碘离子的选择性比其他阴离子（包括其他卤化物）高。芳基三唑镊子S -（-）- 5a和S -（+）- 8a对手性胺显示出显着的对映异构性。使用紫外线和圆二色性（CD）光谱进行手性识别研究。NMR分析已用于建立碘阴离子的连接位点。

  DOI：

  10.1002/jhet.3993
• 作为产物：
  描述：

  (S)-(+)-扁桃酸 、 邻苯二胺 在 盐酸 作用下， 以 水 为溶剂， 生成 (S)-2-(α-hydroxybenzyl)benzimidazole
  参考文献：
  名称：

  Sapre, Jai V.; Khose, Vaibhav N.; Tawde, Trupti S., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2020, vol. 59, # 1, p. 93 - 101

  摘要：

  DOI：
• 作为试剂：
  描述：

  2-溴苯乙酮 在 sodium tetrahydroborate 、 (S)-2-(α-hydroxybenzyl)benzimidazole 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (R)-(-)-2-溴-1-苯乙醇 、 (R)-2-bromo-1-phenylethanol
  参考文献：
  名称：

  新型手性硼氢化物还原剂：9-蒽基三氟甲基酮等羰基化合物的不对称还原

  摘要：

  摘要 合成了(S)-(+)-2-(α-羟基苄基)苯并咪唑(1)和(S)-(-)-2-苯并咪唑-1-乙醇(2)，并将其转化为能还原前手性酮的手性硼氢化物。以高收率（80 至 100%，ee 42 至 95%）制备相应的手性醇。这是1,2-氨基醇改性硼氢化钠的首次报道。

  DOI：

  10.1080/00397919808005078

文献信息

• Synthesis, in vitro cytotoxic and antiviral activity of cis-[Pt(R(–) and S(+)-2-α-hydroxybenzylbenzimidazole)2Cl2] complexes
  作者：M. Gökçe、S. Utku、S. Gür、A. Özkul、F. Gümüş

  DOI：10.1016/j.ejmech.2004.09.017

  日期：2005.2

  A pair of enantiomeric platinum(II) complexes of cis-[Pt(R(-) and S(+)-HBB)(2)Cl-2] (HBB = 2-alpha-hydroxybenzylbenzimidazole) was synthesized and evaluated for its preliminary in vitro cytotoxic activity on the human MCF-7 breast cancer and HeLa cervix cancer cell lines and antiherpes virus activity against bovine herpesvirus type 1 (BHV-1). In general, it was found that Pt(II) complexes were less cytotoxic on both cell lines than cisplatin and were comparable to carboplatin. There was no significant difference in cytotoxicity between two enantiomers, and the antiviral test results showed that the Pt(II) complexes and their carrier ligands R(-) and S(+) HBB had no effects inhibiting replication of BHV-1. (C) 2004 Elsevier SAS. All rights reserved.
• Synthesis and characterization of potential antitumour and antiviral gallium(III) complexes of N-heterocycles
  作者：F. Kratz、B. Nuber、J. Weiß、B.K. Keppler

  DOI：10.1016/s0277-5387(00)83206-4

  日期：1992.1

  Ten water-soluble gallium(III) complexes of N-heterocycles were synthesized and characterized by elemental analysis, conductivity measurements, IR spectroscopy, H-1 NMR spectroscopy and optical activity measurements. Raman spectra were measured with two complexes and an X-ray single-crystal study performed with one complex-trans-dichlorotetrakis-(5-methylpyrazole)gallium(III)tetrachlorogallate(III). The gallium(III) complexes had the general formulae: [L4GaCl2]GaCl4 (L = ligand) (L = indazole, 1,2,3-benzotriazole, pyrazole, 5-methylpyrazole, 4-methylpyrazole), having a trans-octahedral structure (symmetry C(i)), [L4GaCl2]Cl (L = imidazole, benzimidazole), also with a trans-octahedral configuration, and LGaCl2 (L = 2-alpha-oxybenzylbenzimidazolato (HBB) and the respective enantiomers D(-)-HBB and L(+)-HBB) having a tetrahedral structure.So far, eight gallium(III) complexes have been tested in the in vitro anti-HIV test (HIV = human immunodeficiency virus) of the National Cancer Institute (NCI) in the U.S.A., and four of these were found to be moderately active: trans-dichlorotetrakis(5-methylpyrazole)gallium(III) tetrachlorogallate(III), trans-dichlorotetrakis-(4-methylpyrazole)gallium(III)tetrachlorogallate(III), dichloro-(2-alpha-oxybenzylbenzimidazolato-N,O) gallium (III) and trans-dichlorotetrakis(benzimidazole)gallium(III) chloride, the latter exhibiting the highest therapeutic index (TI) of 77. For comparison, the therapeutic index for 3'-azido-3'-deoxythymidine (AZT) ranges from TI = 1000 to 4000.
• Chiral benzimidazole derived bis‐phenyl triazoles as chiroptical sensors for iodide and chiral amines
  作者：Marina E. John、Anil V. Karnik

  DOI：10.1002/jhet.3993

  日期：2020.7

  A series of chiral 2‐hydroxy ethyl/benzyl benzimidazole based aryl triazole tweezers have been prepared using click chemistry in high yields. Chiral pool strategy has been used to obtain the benzimidazole‐based tweezers in very high enantiomerically enriched form. The aryl triazole tweezers, S ‐(−)‐5a and S ‐(+)‐8a displayed a high degree of selectivity for iodide anion over other anions, including

  使用点击化学，已经以高收率制备了一系列手性的2-羟乙基/苄基苯并咪唑基芳基三唑镊子。手性池策略已被用于以对映体富集的形式获得基于苯并咪唑的镊子。芳基三唑镊子S -（-）- 5a和S -（+）- 8a对碘离子的选择性比其他阴离子（包括其他卤化物）高。芳基三唑镊子S -（-）- 5a和S -（+）- 8a对手性胺显示出显着的对映异构性。使用紫外线和圆二色性（CD）光谱进行手性识别研究。NMR分析已用于建立碘阴离子的连接位点。
• Sapre, Jai V.; Khose, Vaibhav N.; Tawde, Trupti S., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, <hi>2020</hi>, vol. 59, # 1, p. 93 - 101
  作者：Sapre, Jai V.、Khose, Vaibhav N.、Tawde, Trupti S.、Wagh, Swapnil J.、Karnik, Anil V.

  DOI：——

  日期：——