(S,S)-1,2-bis(3,5-difluorophenyl)-1,2-ethanediamine

• 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: (S,S)-1,2-bis(3,5-difluorophenyl)-1,2-ethanediamine
• 英文别名: (1S,2S)-1,2-bis(3,5-difluorophenyl)ethane-1,2-diamine
• 化学式: C₁₄H₁₂F₄N₂
• 分子量: 284.256
• InChiKey: DDYGRRLGIOWXDE-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,5,6-五氟苯磺酰氯 、 (S,S)-1,2-bis(3,5-difluorophenyl)-1,2-ethanediamine 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以19%的产率得到(S,S)-C6F5SO2-3,5-F-DPEN
  参考文献：
  名称：

  水中的转移加氢：( E）-β，β-二取代硝基烯烃的对映选择性催化还原

  摘要：

  报道了β，β-二取代的硝基烯烃的轻度催化不对称转移氢化。甲酸与Ir催化剂结合用作还原剂。该反应在低pH值的水中进行并与空气接触，以制备有用的收率和选择性得到加合物。

  DOI：

  10.1021/ol901332e
• 作为产物：
  描述：

  [1-(3,5-Difluoro-phenyl)-meth-(E)-ylidene]-trimethylsilanyl-amine 在 NbCl₄*THF 作用下， 以 乙二醇二甲醚 为溶剂， 生成 (S,S)-1,2-bis(3,5-difluorophenyl)-1,2-ethanediamine 、 (R,R)-1,2-bis(3,5-difluorophenyl)-1,2-ethanediamine
  参考文献：
  名称：

  Electronic Control of Chiral Quaternary Center Creation in the Intramolecular Asymmetric Heck Reaction

  摘要：

  The Boehringer-Ingelheim phosphinoimidazoline (BIPI) ligands were applied to the formation of chiral quaternary centers in the asymmetric Heck reaction. Several different substrates were examined in detail, using more than 70 members of this new ligand class. Hammett relationships were determined through systematic variation of the ligand electronics. All substrates showed essentially the same Hammett behavior, where enantioselectivity increased as the ligands were made more electron-deficient. Ligand optimization has led to catalysts which give the highest enantioselectivities reported to date for these difficult systems.

  DOI：

  10.1021/jo049448z

文献信息

• Transfer Hydrogenation in Water: Enantioselective, Catalytic Reduction of (<i>E</i>)-β,β-Disubstituted Nitroalkenes
  作者：Omid Soltani、Martin A. Ariger、Erick M. Carreira

  DOI：10.1021/ol901332e

  日期：2009.9.17

  A mild catalytic asymmetric transfer hydrogenation of β,β-disubstituted nitroalkenes is reported. Formic acid is used as a reductant in combination with an Ir catalyst. The reaction is conducted in water at low pH and open to air to give adducts in preparatively useful yield and selectivity.

  报道了β，β-二取代的硝基烯烃的轻度催化不对称转移氢化。甲酸与Ir催化剂结合用作还原剂。该反应在低pH值的水中进行并与空气接触，以制备有用的收率和选择性得到加合物。
• Electronic Control of Chiral Quaternary Center Creation in the Intramolecular Asymmetric Heck Reaction
  作者：Carl A. Busacca、Danja Grossbach、Scot J. Campbell、Yong Dong、Magnus C. Eriksson、Robert E. Harris、Paul-James Jones、Ji-Young Kim、Jon C. Lorenz、Keith B. McKellop、Erin M. O'Brien、Fenghe Qiu、Robert D. Simpson、Lana Smith、Regina C. So、Earl M. Spinelli、Jana Vitous、Chiara Zavattaro

  DOI：10.1021/jo049448z

  日期：2004.8.1

  The Boehringer-Ingelheim phosphinoimidazoline (BIPI) ligands were applied to the formation of chiral quaternary centers in the asymmetric Heck reaction. Several different substrates were examined in detail, using more than 70 members of this new ligand class. Hammett relationships were determined through systematic variation of the ligand electronics. All substrates showed essentially the same Hammett behavior, where enantioselectivity increased as the ligands were made more electron-deficient. Ligand optimization has led to catalysts which give the highest enantioselectivities reported to date for these difficult systems.