(4S,5S)-4,5-bis(4-methoxyphenyl)-2-phenyl-4,5-dihydro-1H-imidazole | 1092654-41-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4S,5S)-4,5-bis(4-methoxyphenyl)-2-phenyl-4,5-dihydro-1H-imidazole
• CAS: 1092654-41-5
• 化学式: C₂₃H₂₂N₂O₂
• 分子量: 358.44
• InChiKey: GRFLSOIMVRSZQP-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲亚胺酸乙酯 、 (1S,2S)-1,2-bis(4-methoxyphenyl)ethane-1,2-diamine 以 乙醇 为溶剂， 以66%的产率得到(4S,5S)-4,5-bis(4-methoxyphenyl)-2-phenyl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  On the Racemization of Chiral Imidazolines

  摘要：

  Racemization of chiral imidazolines with base has been studied for the first time following an unexpected finding in the synthesis of chiral imidazoline ligands. Amine bases do not cause racemization. Strong inorganic bases can induce racemization, yet this occurs only when the nitrogen is unsubstituted, in agreement with a symmetry-allowed thermal disrotatory ring opening and closure from a diazapentadienyl anion. Surprisingly, even with electron-withdrawing N-substituents, no racemization is observed. Conditions which allow for the racemization-free manipulations of this important compound class have been defined and developed.

  DOI：

  10.1021/jo8024384
• 作为试剂：
  描述：

  芝麻酚 在 (4S,5S)-4,5-bis(4-methoxyphenyl)-2-phenyl-4,5-dihydro-1H-imidazole 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 144.0h， 生成
  参考文献：
  名称：

  对映和非对映选择性贝蒂/氮杂-迈克尔序列：手性1，3-二取代的异吲哚啉的单操作制备

  摘要：

  报道了使用C 3对称手性三咪唑啉有机催化剂进行的第一对映体和非对映体选择性Betti /分子内氮杂-Michael序列。带有迈克尔受体部分的酚和N-甲苯磺胺类化合物的反应以高收率（≤93％）和优异的对映选择性（≤99.9％）提供了具有两个立体生成中心的致密官能化的1，3-二取代的异吲哚啉，其为单一非对映异构体。

  DOI：

  10.1021/acs.orglett.7b02693

文献信息

• Enantio- and Diastereoselective Betti/aza-Michael Sequence: Single Operated Preparation of Chiral 1,3-Disubstituted Isoindolines
  作者：Shinobu Takizawa、Makoto Sako、Mohamed Ahmed Abozeid、Kenta Kishi、H. D. P. Wathsala、Shuichi Hirata、Kenichi Murai、Hiromichi Fujioka、Hiroaki Sasai

  DOI：10.1021/acs.orglett.7b02693

  日期：2017.10.6

  using a C3-symmetric chiral trisimidazoline organocatalyst is reported. The reaction of phenols and N-tosylimines bearing a Michael acceptor moiety afforded densely functionalized 1,3-disubstituted isoindolines bearing two stereogenic centers as single diastereomers in high yields (≤93%) and excellent enantioselectivities (≤99.9%).

  报道了使用C 3对称手性三咪唑啉有机催化剂进行的第一对映体和非对映体选择性Betti /分子内氮杂-Michael序列。带有迈克尔受体部分的酚和N-甲苯磺胺类化合物的反应以高收率（≤93％）和优异的对映选择性（≤99.9％）提供了具有两个立体生成中心的致密官能化的1，3-二取代的异吲哚啉，其为单一非对映异构体。
• On the Racemization of Chiral Imidazolines
  作者：Carl A. Busacca、Teresa Bartholomeyzik、Sreedhar Cheekoori、Nelu Grinberg、Heewon Lee、Shengli Ma、Anjan Saha、Sherry Shen、Chris H. Senanayake

  DOI：10.1021/jo8024384

  日期：2008.12.19

  Racemization of chiral imidazolines with base has been studied for the first time following an unexpected finding in the synthesis of chiral imidazoline ligands. Amine bases do not cause racemization. Strong inorganic bases can induce racemization, yet this occurs only when the nitrogen is unsubstituted, in agreement with a symmetry-allowed thermal disrotatory ring opening and closure from a diazapentadienyl anion. Surprisingly, even with electron-withdrawing N-substituents, no racemization is observed. Conditions which allow for the racemization-free manipulations of this important compound class have been defined and developed.