1-[(3,5-dimethylphenyl)methyl]-2-[(1-methylethyl)thio]benzimidazole | 634193-85-4

• 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-[(3,5-dimethylphenyl)methyl]-2-[(1-methylethyl)thio]benzimidazole
• CAS: 634193-85-4
• 化学式: C₁₉H₂₂N₂S
• 分子量: 310.463
• InChiKey: WVMHPZXSIKALRC-UHFFFAOYSA-N

物化性质

• 沸点：
  477.8±55.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-[(3,5-dimethylphenyl)methyl]-2-[(1-methylethyl)thio]benzimidazole 在 正丁基锂 、 zinc trifluoromethanesulfonate 、 (S,S)-2,2'-异亚丙基双(4-苯基-2-恶唑啉) 、 二异丙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 (S)-1-[(3,5-dimethylphenyl)methyl]-2-[(1,3,3-trimethylbutyl)sulfonyl]benzimidazole
  参考文献：
  名称：

  Enantioselective hydrogen atom transfer to α-sulfonyl radicals controlled by selective coordination of a chiral Lewis acid to an enantiotopic sulfonyl oxygen

  摘要：

  Enantioselective hydrogen atom transfer to a-sulfonyl radicals generated from the alkyl radical addition to 2-propenyl and 1-phenylethenyl sulfones in the presence of chiral Lewis acids affords products with high enantioselectivity. The stereochemical course is discussed with the transition states involving selective coordination of a chiral Lewis acid to an enantiotopic sulfonyl oxygen. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00531-7
• 作为产物：
  描述：

  (9ci)-2-[(1-甲基乙基)硫代]-1H-苯并咪唑 、 3,5-二甲基溴苄 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以81%的产率得到1-[(3,5-dimethylphenyl)methyl]-2-[(1-methylethyl)thio]benzimidazole
  参考文献：
  名称：

  Enantioselective hydrogen atom transfer to α-sulfonyl radicals controlled by selective coordination of a chiral Lewis acid to an enantiotopic sulfonyl oxygen

  摘要：

  Enantioselective hydrogen atom transfer to a-sulfonyl radicals generated from the alkyl radical addition to 2-propenyl and 1-phenylethenyl sulfones in the presence of chiral Lewis acids affords products with high enantioselectivity. The stereochemical course is discussed with the transition states involving selective coordination of a chiral Lewis acid to an enantiotopic sulfonyl oxygen. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00531-7

文献信息

• Enantioselective hydrogen atom transfer to α-sulfonyl radicals controlled by selective coordination of a chiral Lewis acid to an enantiotopic sulfonyl oxygen
  作者：Hideki Sugimoto、Shuichi Nakamura、Yoshihiko Watanabe、Takeshi Toru

  DOI：10.1016/s0957-4166(03)00531-7

  日期：2003.10

  Enantioselective hydrogen atom transfer to a-sulfonyl radicals generated from the alkyl radical addition to 2-propenyl and 1-phenylethenyl sulfones in the presence of chiral Lewis acids affords products with high enantioselectivity. The stereochemical course is discussed with the transition states involving selective coordination of a chiral Lewis acid to an enantiotopic sulfonyl oxygen. (C) 2003 Elsevier Ltd. All rights reserved.