(S,S)-N,N'-bis(1-diphenylphosphinomethyl-2-methyl-propyl)oxaldiamide | 263024-60-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S,S)-N,N'-bis(1-diphenylphosphinomethyl-2-methyl-propyl)oxaldiamide
• 英文别名: N,N'-bis[(2S)-1-diphenylphosphanyl-3-methylbutan-2-yl]oxamide
• CAS: 263024-60-8
• 化学式: C₃₆H₄₂N₂O₂P₂
• 分子量: 596.689
• InChiKey: NPORGNBNCHDAES-KKLWWLSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S,S)-N,N'-bis(1-diphenylphosphinomethyl-2-methyl-propyl)oxaldiamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以75%的产率得到(S,S)-N,N'-bis(1-diphenylphosphinomethyl-2-methyl-propyl)ethylen-1,2-diamine
  参考文献：
  名称：

  Synthesis of Heterofunctionalized Multidentate Diphosphines

  摘要：

  The synthesis of new chiral multidentate amino- and amidophosphine ligands bearing up to six potential coordination sites were synthesized starting from L-valine. Based on these compounds chiral Ru(II) complexes were prepared, characterized and tested in the asymmetric transfer hydrogenation of aryl-alkyl ketones. In all cases investigated the catalyst bearing additional hydroxy groups gave lower conversions than the complex without hydroxy groups. Highest enantioselectivity was achieved with isobutyrophenone as substrate (69%ee). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01075-3
• 作为产物：
  描述：

  (S)-2-(N-tert-butoxycarbonylamino)-3-methylbutyl tosylate 在 氢溴酸 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 (S,S)-N,N'-bis(1-diphenylphosphinomethyl-2-methyl-propyl)oxaldiamide
  参考文献：
  名称：

  Synthesis of Heterofunctionalized Multidentate Diphosphines

  摘要：

  The synthesis of new chiral multidentate amino- and amidophosphine ligands bearing up to six potential coordination sites were synthesized starting from L-valine. Based on these compounds chiral Ru(II) complexes were prepared, characterized and tested in the asymmetric transfer hydrogenation of aryl-alkyl ketones. In all cases investigated the catalyst bearing additional hydroxy groups gave lower conversions than the complex without hydroxy groups. Highest enantioselectivity was achieved with isobutyrophenone as substrate (69%ee). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01075-3

文献信息

• Induction of reversal chirality by C2-symmetric diamide linked-diphosphine ligands in catalytic asymmetric allylations
  作者：Akihito Saitoh、Takashi Uda、Toshiaki Morimoto

  DOI：10.1016/s0957-4166(00)00397-9

  日期：2000.10

  diphosphine ligands 1 were varied using various kinds of diacyl chlorides. The ligand 1c derived from phthaloyl chloride, which was remarkably effective in the asymmetric induction on palladium-catalyzed asymmetric allylic substitutions of 2-cyclohexenyl pivalate or acetate, exhibited a moderate level of enantioselectivity, 72% ee, in the transformations of 1,3-diphenyl-2-propenyl pivalate. The newly developed

  使用各种二酰氯改变C 2对称二膦配体1的两个酰胺骨架之间的桥连部分X。衍生自邻苯二甲酰氯的配体1c在钯催化的2-环己烯基新戊酸酯或乙酸酯的钯催化的不对称烯丙基取代中的不对称诱导中非常有效，在1,3-转化中表现出中等水平的对映选择性，ee为72％。二苯基-2-丙烯基新戊酸酯。具有一个碳间隔基X的新开发的配体1g – i表现出更高的对映体过量度，最高可达93％ee。有趣的是，目前的反应是由Pd- 1c - e催化的，克- Ĵ得到产物的复合物4与相对的绝对构š使用VALAP，其具有相同的手性源为的反应相比，1。尽管产率非常低，但配体1a，b，f显示出R构型的诱导。在Pr / Mr手性模型的基础上讨论了S - 4的产生。
• Synthesis of Heterofunctionalized Multidentate Diphosphines
  作者：Michael Quirmbach、Jens Holz、Vitali I Tararov、Armin Börner

  DOI：10.1016/s0040-4020(99)01075-3

  日期：2000.1

  The synthesis of new chiral multidentate amino- and amidophosphine ligands bearing up to six potential coordination sites were synthesized starting from L-valine. Based on these compounds chiral Ru(II) complexes were prepared, characterized and tested in the asymmetric transfer hydrogenation of aryl-alkyl ketones. In all cases investigated the catalyst bearing additional hydroxy groups gave lower conversions than the complex without hydroxy groups. Highest enantioselectivity was achieved with isobutyrophenone as substrate (69%ee). (C) 2000 Elsevier Science Ltd. All rights reserved.