bis(N-(3-buten-1-yl)benzoimidazole) | 1374668-50-4

• 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: bis(N-(3-buten-1-yl)benzoimidazole)
• 英文别名: 1-But-3-enyl-2-(1-but-3-enylbenzimidazol-2-yl)benzimidazole；1-but-3-enyl-2-(1-but-3-enylbenzimidazol-2-yl)benzimidazole
• CAS: 1374668-50-4
• 化学式: C₂₂H₂₂N₄
• 分子量: 342.443
• InChiKey: PARPFBKCPQWUDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(N-(3-buten-1-yl)benzoimidazole) 在 (pyrrolyl)₂Mo(=CHCMe₂Ph)(=N-C₆H₃-2,6-ⁱPr₂) 、 3,3'-di-tert-butyl-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diol 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 di(benzo[d]imidazo)[1,2-a:2,1-c]1,8-diaza-7-(E)-cyclodecene
  参考文献：
  名称：

  钼催化的不对称环封闭复分解对不对称大环杂二芳基衍生物的对映选择性合成

  摘要：

  藤蔓状分子不对称性是通过手性钼催化剂的对映选择性闭环复分解反应引起的。反应在温和条件下通过E选择性闭环复分解反应进行，产生对映选择性高达96％ee的大环双唑。

  DOI：

  10.1002/anie.201500459
• 作为产物：
  描述：

  1-(3-丁烯-1-基)-1H-苯并咪唑 在 silver carbonate 、 氧气 、 copper diacetate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 24.0h， 以88%的产率得到bis(N-(3-buten-1-yl)benzoimidazole)
  参考文献：
  名称：

  Axially Chiral Macrocyclic E-Alkene Bearing Bisazole Component Formed by Sequential C–H Homocoupling and Ring-Closing Metathesis

  摘要：

  Clipping by ring-closing metathesis freezes rotation of a C-C bond to result in forming axial chirality. Treatment of bisbenzimidazole bearing an N-(3-butenyl) substituent with a Grubbs' catalyst undergoes ring-closing metathesis, in which the stereochemistry of the thus formed olefin was exclusively E-form. Analysis by HPLC with a chiral stationary column confirmed clear baseline separation of each enantiomer.

  DOI：

  10.1021/ol300755y

文献信息

• Absolute structure determination of compounds with axial and planar chirality using the crystalline sponge method
  作者：Shota Yoshioka、Yasuhide Inokuma、Manabu Hoshino、Takashi Sato、Makoto Fujita

  DOI：10.1039/c5sc01681a

  日期：——

  The absolute stereochemistry of compounds with axial and planar chirality is successfully determined by the crystalline sponge method without crystallization or derivatization of the compounds. This method is applied to...

  通过结晶海绵法成功测定了具有轴向和平面手性化合物的绝对立体化学，无需化合物结晶或衍生化。该方法适用于...
• Enantioselective Synthesis of Macrocyclic Heterobiaryl Derivatives of Molecular Asymmetry by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis
  作者：Yoichi Okayama、Satoru Tsuji、Yuka Toyomori、Atsunori Mori、Sachie Arae、Wei-Yi Wu、Tamotsu Takahashi、Masamichi Ogasawara

  DOI：10.1002/anie.201500459

  日期：2015.4.13

  Winding vine‐shaped molecular asymmetry is induced by enantioselective ring‐closing metathesis with a chiral molybdenum catalyst. The reaction proceeds under mild conditions through an E‐selective ring‐closing metathesis leading to macrocyclic bisazoles with enantioselectivities of up to 96 % ee.

  藤蔓状分子不对称性是通过手性钼催化剂的对映选择性闭环复分解反应引起的。反应在温和条件下通过E选择性闭环复分解反应进行，产生对映选择性高达96％ee的大环双唑。
• Axially Chiral Macrocyclic <i>E</i>-Alkene Bearing Bisazole Component Formed by Sequential C–H Homocoupling and Ring-Closing Metathesis
  作者：Shotaro Nishio、Takashi Somete、Atsushi Sugie、Tohru Kobayashi、Tsuyoshi Yaita、Atsunori Mori

  DOI：10.1021/ol300755y

  日期：2012.5.18

  Clipping by ring-closing metathesis freezes rotation of a C-C bond to result in forming axial chirality. Treatment of bisbenzimidazole bearing an N-(3-butenyl) substituent with a Grubbs' catalyst undergoes ring-closing metathesis, in which the stereochemistry of the thus formed olefin was exclusively E-form. Analysis by HPLC with a chiral stationary column confirmed clear baseline separation of each enantiomer.