{(2R,5R)-1-[2-((2R,5R)-2,5-Bis-hydroxymethyl-phospholan-1-yl)-phenyl]-5-hydroxymethyl-phospholan-2-yl}-methanol | 376647-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {(2R,5R)-1-[2-((2R,5R)-2,5-Bis-hydroxymethyl-phospholan-1-yl)-phenyl]-5-hydroxymethyl-phospholan-2-yl}-methanol
• 英文别名: [(2R,5R)-1-[2-[(2R,5R)-2,5-bis(hydroxymethyl)phospholan-1-yl]phenyl]-5-(hydroxymethyl)phospholan-2-yl]methanol
• CAS: 376647-42-6
• 化学式: C₁₈H₂₈O₄P₂
• 分子量: 370.365
• InChiKey: VIXNEGNWAVFBKU-KLHDSHLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [rhodium(I)(norborna-2,5-diene)2]SbF₆ 、 {(2R,5R)-1-[2-((2R,5R)-2,5-Bis-hydroxymethyl-phospholan-1-yl)-phenyl]-5-hydroxymethyl-phospholan-2-yl}-methanol 以 氘代甲醇 为溶剂， 生成 (C6H4(PC4H6(CH2OH)2)2)Rh(norbornadiene)[SbF6]
  参考文献：
  名称：

  Synthesis, Characterization, and Applicability of Neutral Polyhydroxy Phospholane Derivatives and Their Rhodium(I) Complexes for Reactions in Organic and Aqueous Media

  摘要：

  Two different protocols for the preparation of water-soluble, enantiomerically pure polyhydroxybisphospholanes from acid-labile acetal and tert-butyldimethylsilyl-protected derivatives are reported. These procedures circumvent two of the commonly encountered limitations in the synthesis of these potentially important ligands: (a) formation of phosphonium salts from the highly basic phosphine under acidic conditions, and (b) the need to start with preformed, fully protected cationic metal complex. Thus, cationic Rh complexes of these ligands have been prepared in a separate step, and they have been found to be excellent catalysts for organic and aqueous phase hydrogenation of dehydroamino acids. The viability of catalyst recovery has been demonstrated in three different systems, including two cases where > 99% ee can be achieved under recycling conditions.

  DOI：

  10.1021/ja011500a
• 作为产物：
  描述：

  [(2R,5R)-1-[2-[(2R,5R)-2,5-bis[[tert-butyl(dimethyl)silyl]oxymethyl]phospholan-1-yl]phenyl]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]phospholan-2-yl]methoxy-tert-butyl-dimethylsilane 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以84%的产率得到{(2R,5R)-1-[2-((2R,5R)-2,5-Bis-hydroxymethyl-phospholan-1-yl)-phenyl]-5-hydroxymethyl-phospholan-2-yl}-methanol
  参考文献：
  名称：

  Synthesis, Characterization, and Applicability of Neutral Polyhydroxy Phospholane Derivatives and Their Rhodium(I) Complexes for Reactions in Organic and Aqueous Media

  摘要：

  Two different protocols for the preparation of water-soluble, enantiomerically pure polyhydroxybisphospholanes from acid-labile acetal and tert-butyldimethylsilyl-protected derivatives are reported. These procedures circumvent two of the commonly encountered limitations in the synthesis of these potentially important ligands: (a) formation of phosphonium salts from the highly basic phosphine under acidic conditions, and (b) the need to start with preformed, fully protected cationic metal complex. Thus, cationic Rh complexes of these ligands have been prepared in a separate step, and they have been found to be excellent catalysts for organic and aqueous phase hydrogenation of dehydroamino acids. The viability of catalyst recovery has been demonstrated in three different systems, including two cases where > 99% ee can be achieved under recycling conditions.

  DOI：

  10.1021/ja011500a

文献信息

• Synthesis, Characterization, and Applicability of Neutral Polyhydroxy Phospholane Derivatives and Their Rhodium(I) Complexes for Reactions in Organic and Aqueous Media
  作者：T. V. RajanBabu、Yuan-Yong Yan、Seunghoon Shin

  DOI：10.1021/ja011500a

  日期：2001.10.1

  Two different protocols for the preparation of water-soluble, enantiomerically pure polyhydroxybisphospholanes from acid-labile acetal and tert-butyldimethylsilyl-protected derivatives are reported. These procedures circumvent two of the commonly encountered limitations in the synthesis of these potentially important ligands: (a) formation of phosphonium salts from the highly basic phosphine under acidic conditions, and (b) the need to start with preformed, fully protected cationic metal complex. Thus, cationic Rh complexes of these ligands have been prepared in a separate step, and they have been found to be excellent catalysts for organic and aqueous phase hydrogenation of dehydroamino acids. The viability of catalyst recovery has been demonstrated in three different systems, including two cases where > 99% ee can be achieved under recycling conditions.