(S)-2-methoxy-N-(phenyl(1-phenyl-1H-1,2,3-triazol-4-yl)methyl)aniline | 1041403-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-2-methoxy-N-(phenyl(1-phenyl-1H-1,2,3-triazol-4-yl)methyl)aniline
• 英文别名: 2-methoxy-N-[phenyl(1-phenyl-1H-1,2,3-triazol-4-yl)methyl]aniline
• CAS: 1041403-34-2
• 化学式: C₂₂H₂₀N₄O
• 分子量: 356.427
• InChiKey: FVFBFISIDGETFM-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.97
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-methoxy-N-(phenyl(1-phenyl-1H-1,2,3-triazol-4-yl)methyl)aniline 、 氯二异丙基膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.25h， 生成
  参考文献：
  名称：

  Enantioselective Synthesis of Tunable Chiral Clickphine P,N-Ligands and Their Application in Ir-Catalyzed Asymmetric Hydrogenation

  摘要：

  A small library of highly tunable chiral Clickphine P,N-ligands has been prepared in an enantioselective fashion by Cu-I-catalyzed asymmetric propargylic amination using a single chiral complex and a subsequent in situ cycloaddition click reaction. The scope of the propargylic amination to yield optically active triazolyl amines is described. The amines are transformed in a one-pot procedure to the corresponding Ir-Clickphine complexes, which serve as catalysts for the asymmetric hydrogenation of di-, tri-, and tetrasubstituted unfunctionalized alkenes. Enantioselectivities of up to 90% ee were obtained in these hydrogenations, which are among the best reported in the case of the tetrasubstituted substrate 2-(4 '-methoxyphenyl)-3-methylbut-2-ene (9) (87% ee). This is a demonstration of the effective use of the chiral pool, as from one chiral catalyst a library of chiral Ir complexes has been synthesized that can hydrogenate various alkenes with high selectivity.

  DOI：

  10.1021/acs.joc.5b00438
• 作为产物：
  描述：

  1-phenylprop-2-ynyl acetate 在 copper(l) iodide 、 N,N-二异丙基乙胺 、 2,6-bis((4S,5R)-4,5-diphenyl-4,5-dihydrooxazol-2-yl)pyridine 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 (S)-2-methoxy-N-(phenyl(1-phenyl-1H-1,2,3-triazol-4-yl)methyl)aniline
  参考文献：
  名称：

  Enantioselective Synthesis of Tunable Chiral Clickphine P,N-Ligands and Their Application in Ir-Catalyzed Asymmetric Hydrogenation

  摘要：

  A small library of highly tunable chiral Clickphine P,N-ligands has been prepared in an enantioselective fashion by Cu-I-catalyzed asymmetric propargylic amination using a single chiral complex and a subsequent in situ cycloaddition click reaction. The scope of the propargylic amination to yield optically active triazolyl amines is described. The amines are transformed in a one-pot procedure to the corresponding Ir-Clickphine complexes, which serve as catalysts for the asymmetric hydrogenation of di-, tri-, and tetrasubstituted unfunctionalized alkenes. Enantioselectivities of up to 90% ee were obtained in these hydrogenations, which are among the best reported in the case of the tetrasubstituted substrate 2-(4 '-methoxyphenyl)-3-methylbut-2-ene (9) (87% ee). This is a demonstration of the effective use of the chiral pool, as from one chiral catalyst a library of chiral Ir complexes has been synthesized that can hydrogenate various alkenes with high selectivity.

  DOI：

  10.1021/acs.joc.5b00438

文献信息

• 一种手性炔丙基胺化合物的催化不对称合成方 法
  申请人：中国科学院大连化学物理研究所

  公开号：CN104693143B

  公开（公告）日：2016-10-05

  一种手性炔丙基胺化合物的催化不对称合成方法，以手性铜催化剂催化碳酸酰胺炔丙酯类化合物的分子内不对称脱羧反应合成手性炔丙基胺化合物；采用的手性铜催化剂是由铜盐与手性P,N,N‑三齿配体在各种极性和非极性溶剂中原位生成。本发明可以方便地合成各种带取代基团的手性炔丙基胺化合物，其对映体过量百分数超过90%。本发明具有操作简单、原料易得、底物适用范围广、对映选择性高等特点。
• Enantioselective Copper-Catalyzed Propargylic Amination
  作者：Remko J. Detz、Mariëlle M. E. Delville、Henk Hiemstra、Jan H. van Maarseveen

  DOI：10.1002/anie.200705264

  日期：2008.5.5