2,6-双[(4R,5R)-4,5-二氢-4,5-二苯基-1H-咪唑-2-基]吡啶 | 863491-46-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2,6-双[(4R,5R)-4,5-二氢-4,5-二苯基-1H-咪唑-2-基]吡啶
• 英文名称: 2,6-bis([4R,5R]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)pyridine
• 英文别名: 2,6-Bis((4R,5R)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)pyridine；2,6-bis[(4R,5R)-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl]pyridine
• CAS: 863491-46-7
• 化学式: C₃₅H₂₉N₅
• 分子量: 519.649
• InChiKey: APPVMXCHSLHBIP-XEXPGFJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2,6-双[(4R,5R)-4,5-二氢-4,5-二苯基-1H-咪唑-2-基]吡啶 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-(1-((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl-3-oxycarbonyl)-[4R,5R]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)-6-(1-(acetyl)-[4R,5R]-4,5-diphenyl-4,5-dihydro-1H-imidazol-2-yl)pyridine
  参考文献：
  名称：

  Synthesis of a novel class of chiral N,N,N-tridentate pyridinebisimidazoline ligands and their application in Ru-catalyzed asymmetric epoxidations

  摘要：

  A new class of easily tunable N,N,N-pyridinebisimidazoline (pybim) ligands have been synthesized. The synthesis and tunability of these chiral tridentate ligands are much easier and flexible compared to the popular pyboxes, making the former a suitable ligand tool box for various asymmetric transformations. Ruthenium complexes of the new ligands were synthesized and applied in the asymmetric epoxidation of olefins using hydrogen peroxide as the oxidant. Excellent yields and moderate to good enantioselectivities were achieved in the epoxidation of aromatic olefins. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.060
• 作为产物：
  描述：

  2,6-吡啶二甲腈 在 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 88.0h， 生成 2,6-双[(4R,5R)-4,5-二氢-4,5-二苯基-1H-咪唑-2-基]吡啶
  参考文献：
  名称：

  新型手性N，N，N-三齿吡啶双咪唑啉配体库的合成及其在Ru催化的不对称环氧化中的应用。

  摘要：

  首次合成了手性三齿N，N，N-吡啶双咪唑啉的小型配体库。这类新型的配体可以很容易地在多g级上调节和合成。配体的有用性在用过氧化氢作为氧化剂的钌催化的不对称环氧化中显示。对于芳族烯烃的环氧化，已经获得了优异的收率（> 99％）和良好的对映选择性（最高71％ee）。[反应：看文字]

  DOI：

  10.1021/ol050821e
• 作为试剂：
  描述：

  N-甲基吲哚酮 在 2,6-双[(4R,5R)-4,5-二氢-4,5-二苯基-1H-咪唑-2-基]吡啶 、 四丁基硫酸氢铵 、 potassium carbonate 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 102.5h， 生成 、 3,3-Bis[(1-benzyltriazol-4-yl)methyl]-1-methylindol-2-one
  参考文献：
  名称：

  不对称铜（I）催化叠氮-炔烃环加成到四元吲哚

  摘要：

  我们报告了通过基于羟吲哚的 1,6-庚二炔的不对称去对称化的高度对映选择性的 Cu(I) 催化的叠氮化物-炔烃环加成反应，该反应提供了带有 1,2,3-三唑部分的四元羟吲哚和 84-98% ee .

  DOI：

  10.1021/ja4066656

文献信息

• Facile Preparation of 2-Imidazolines from Aldehydes with <i>tert</i>-Butyl Hypochlorite
  作者：Hideo Togo、Midori Ishihara

  DOI：10.1055/s-2007-983726

  日期：2007.7

  An efficient and high-yield preparation of 2-imidazolines was achieved from aldehydes and ethylenediamines in the presence of tert-butyl hypochlorite. By this method, 1,3-bis(imidazolin-2-yl)benzene and 2,6-bis(imidazolin-2-yl)pyridine, which act as chiral ligands, could be prepared directly from the corresponding dialdehydes in high yields.

  在次氯酸叔丁酯存在下，由醛和乙二胺高效、高产地制备 2-咪唑啉。通过该方法，可以直接由相应的二醛高收率地制备出作为手性配体的1,3-双(咪唑啉-2-基)苯和2,6-双(咪唑啉-2-基)吡啶。
• Palladium-Catalyzed Multicomponent Synthesis of 2-Aryl-2-imidazolines from Aryl Halides and Diamines
  作者：Joanna V. Geden、Alpa K. Pancholi、Michael Shipman

  DOI：10.1021/jo400252n

  日期：2013.4.19

  An efficient palladium-catalyzed three-component reaction that combines aryl halides, isocyanides, and diamines provides access to 2-aryl-2-imidazolines in yields up to 96%. Through variation of the diamine component, the reaction can be extended to the synthesis of 2-aryl-1H-benzimidazoles and 2-aryl-1,4,5,6-tetrahydropyrimidines.
• Synthesis of a novel class of chiral N,N,N-tridentate pyridinebisimidazoline ligands and their application in Ru-catalyzed asymmetric epoxidations
  作者：Gopinathan Anilkumar、Santosh Bhor、Man Kin Tse、Markus Klawonn、Bianca Bitterlich、Matthias Beller

  DOI：10.1016/j.tetasy.2005.08.060

  日期：2005.10

  A new class of easily tunable N,N,N-pyridinebisimidazoline (pybim) ligands have been synthesized. The synthesis and tunability of these chiral tridentate ligands are much easier and flexible compared to the popular pyboxes, making the former a suitable ligand tool box for various asymmetric transformations. Ruthenium complexes of the new ligands were synthesized and applied in the asymmetric epoxidation of olefins using hydrogen peroxide as the oxidant. Excellent yields and moderate to good enantioselectivities were achieved in the epoxidation of aromatic olefins. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of a New Chiral <i>N,N,N</i>-Tridentate Pyridinebisimidazoline Ligand Library and Its Application in Ru-Catalyzed Asymmetric Epoxidation
  作者：Santosh Bhor、Gopinathan Anilkumar、Man Kin Tse、Markus Klawonn、Christian Döbler、Bianca Bitterlich、Anne Grotevendt、Matthias Beller

  DOI：10.1021/ol050821e

  日期：2005.8.1

  A small ligand library of chiral tridentate N,N,N-pyridinebisimidazolines have been synthesized for the first time. This new class of ligands can be easily tuned and synthesized on multi g-scale. The usefulness of the ligands is shown in the ruthenium-catalyzed asymmetric epoxidation with hydrogen peroxide as oxidant. Excellent yields (>99%) and good enantioselectivities (up to 71% ee) have been obtained

  首次合成了手性三齿N，N，N-吡啶双咪唑啉的小型配体库。这类新型的配体可以很容易地在多g级上调节和合成。配体的有用性在用过氧化氢作为氧化剂的钌催化的不对称环氧化中显示。对于芳族烯烃的环氧化，已经获得了优异的收率（> 99％）和良好的对映选择性（最高71％ee）。[反应：看文字]