1-[(2E)-1-oxo-3-phenyl-2-propenyl]-1H-benzoimidazole | 370084-07-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-[(2E)-1-oxo-3-phenyl-2-propenyl]-1H-benzoimidazole
• 英文别名: 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole；(E)-1-(1H-benzo[d]imidazol-1-yl)-3-phenylprop-2-en-1-one；1-Benzoimidazol-1-yl-3-phenyl-propenone；(E)-1-(benzimidazol-1-yl)-3-phenylprop-2-en-1-one
• CAS: 370084-07-4
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: SHUWQFLKYAKUGO-ZHACJKMWSA-N

物化性质

• 沸点：
  457.9±38.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(2E)-1-oxo-3-phenyl-2-propenyl]-1H-benzoimidazole 在 La-(S)-BINOL-Ph₃AsO 、 4 A molecular sieve 、 红铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 (2R,3S)-3-phenyloxirane-2-carbaldehyde
  参考文献：
  名称：

  镧系元素-BINOL配合物催化α，β-不饱和羧酸咪唑化物和酰胺的不对称环氧化

  摘要：

  研究了α，β-不饱和羧酸咪唑化物和简单酰胺的高度对映选择性催化不对称环氧化反应。在5-10 mol％的镧系元素-BINOL配合物的存在下，反应在高底物普遍性下可顺利进行。特别地，在α，β-不饱和酰胺的情况下，几乎具有完美的对映选择性（> 99％ee）。相应的环氧化物已成功转化为多种类型的有用手性化合物，例如α，β-环氧酯，α，β-环氧酰胺，α，β-环氧醛，α，β-环氧β-酮酸酯，α-和β-羟基羰基化合物。进行B3LYP密度泛函研究以预测底物反应性。

  DOI：

  10.1016/j.tet.2003.06.010
• 作为产物：
  描述：

  苯并咪唑 、 3-苯基-2-丙烯酰氯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以86%的产率得到1-[(2E)-1-oxo-3-phenyl-2-propenyl]-1H-benzoimidazole
  参考文献：
  名称：

  Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives

  摘要：

  Series of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives were synthesized and characterized by spectral methods. Among 21 derivatives, single crystals of 3a and 3l were grown and their structural parameters were evaluated. Newly synthesized compounds were screened for anti-tubercular activity and the MIC was determined against Mycobacterium tuberculosis H37Rv by Microplate Alamar Blue Assay (MABA) method. Majority of the compounds exhibited a promising inhibition of M. tuberculosis and the molecules functionalized with electron-donating groups at C-2 carbon of benzimidazole moiety were found to be more active in inhibiting M. tuberculosis. Further, more promising compounds viz., 3b, 3i and 3l were tested for their cytotoxic activity. Compound 3l was found to display excellent activity (IC50 < 10 mu g mL(-1)) with 100% cell lysis at 30 mu g mL(-1) concentration against A549 (Human lung carcinoma) and 8E5 (Human; Acute Lymphoblastic Leukemia) cell lines. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.017

文献信息

• Catalytic Asymmetric Synthesis of α,β-Epoxy Esters, Aldehydes, Amides, and γ,δ-Epoxy β-Keto Esters:  Unique Reactivity of α,β-Unsaturated Carboxylic Acid Imidazolides
  作者：Tetsuhiro Nemoto、Takashi Ohshima、Masakatsu Shibasaki

  DOI：10.1021/ja0164879

  日期：2001.9.1
• Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives
  作者：Veerendra Kumar A. Kalalbandi、J. Seetharamappa、Umesha Katrahalli、Kishore G. Bhat

  DOI：10.1016/j.ejmech.2014.04.017

  日期：2014.5

  Series of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives were synthesized and characterized by spectral methods. Among 21 derivatives, single crystals of 3a and 3l were grown and their structural parameters were evaluated. Newly synthesized compounds were screened for anti-tubercular activity and the MIC was determined against Mycobacterium tuberculosis H37Rv by Microplate Alamar Blue Assay (MABA) method. Majority of the compounds exhibited a promising inhibition of M. tuberculosis and the molecules functionalized with electron-donating groups at C-2 carbon of benzimidazole moiety were found to be more active in inhibiting M. tuberculosis. Further, more promising compounds viz., 3b, 3i and 3l were tested for their cytotoxic activity. Compound 3l was found to display excellent activity (IC50 < 10 mu g mL(-1)) with 100% cell lysis at 30 mu g mL(-1) concentration against A549 (Human lung carcinoma) and 8E5 (Human; Acute Lymphoblastic Leukemia) cell lines. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Catalytic asymmetric epoxidation of α,β-unsaturated carboxylic acid imidazolides and amides by lanthanide–BINOL complexes
  作者：Takashi Ohshima、Tetsuhiro Nemoto、Shin-ya Tosaki、Hiroyuki Kakei、Vijay Gnanadesikan、Masakatsu Shibasaki

  DOI：10.1016/j.tet.2003.06.010

  日期：2003.12

  Highly enantioselective catalytic asymmetric epoxidation of α,β-unsaturated carboxylic acid imidazolides and simple amides was developed. In the presence of 5–10 mol% of lanthanide–BINOL complexes, the reaction proceeded smoothly with high substrate generality. In particular, in the cases of α,β-unsaturated amides, there was nearly perfect enantioselectivity (>99% ee). The corresponding epoxides were

  研究了α，β-不饱和羧酸咪唑化物和简单酰胺的高度对映选择性催化不对称环氧化反应。在5-10 mol％的镧系元素-BINOL配合物的存在下，反应在高底物普遍性下可顺利进行。特别地，在α，β-不饱和酰胺的情况下，几乎具有完美的对映选择性（> 99％ee）。相应的环氧化物已成功转化为多种类型的有用手性化合物，例如α，β-环氧酯，α，β-环氧酰胺，α，β-环氧醛，α，β-环氧β-酮酸酯，α-和β-羟基羰基化合物。进行B3LYP密度泛函研究以预测底物反应性。