(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane | 156145-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane
• 英文别名: (4S,5S)-4-(diphenylphosphinomethyl)-2,2-dimethyl-5-(2-pyridyl)-1,3-dioxolane；4-(diphenylphosphinomethyl)-2,2-dimethyl-5-(2-pyridyl)-1,3-dioxolane；Py-diphos；[(4R,5S)-2,2-dimethyl-5-pyridin-2-yl-1,3-dioxolan-4-yl]methyl-diphenylphosphane
• CAS: 156145-73-2
• 化学式: C₂₃H₂₄NO₂P
• 分子量: 377.423
• InChiKey: MDIBSCDCEKKQJZ-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane 在 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane P-oxide
  参考文献：
  名称：

  Synthesis of homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane: Use in asymmetric catalysis

  摘要：

  Homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane were prepared from L-(+)-tartrate. These compounds were assessed in metal catalyzed asymmetric addition of diethylzinc to benzaldehyde, hydroformylation of styrene, hydrocarboethoxylation of styrene and allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00086-9
• 作为产物：
  描述：

  (4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane 在 4-二甲氨基吡啶 、 decamethylrhenocene 、 四丁基氟化铵 、 sodium 、 氢化钾 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 25.0~120.0 ℃ 、1.42 MPa 条件下， 反应 42.0h， 生成 (4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Synthesis of homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane: Use in asymmetric catalysis

  摘要：

  Homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane were prepared from L-(+)-tartrate. These compounds were assessed in metal catalyzed asymmetric addition of diethylzinc to benzaldehyde, hydroformylation of styrene, hydrocarboethoxylation of styrene and allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00086-9

文献信息

• Synthesis and characterization of square-planar palladium(II), platinum(II) and rhodium(I) complexes with a chiral pyridylphosphine hybrid ligand
  作者：Sergio Stoccoro、Giorgio Chelucci、Antonio Zucca、Maria Agostina Cinellu、Giovanni Minghetti、Mario Manassero

  DOI：10.1039/dt9960001295

  日期：——

  structure of compound 1 has been solved by X-ray diffraction: the ligand is co-ordinated through both the P and N atoms to form a seven-membered ring which adopts a chair conformation. One of the hydrogen atoms of the backbone is located 2.72(3)Å over the palladium atom in a pseudo-axial position. Spectroscopic evidence supports a chelating behaviour of the ligand also in compounds 2 and 3. The behaviour of

  配合物[PdLCl 2 ] 1，[PtLCl 2 ] 2，[PtL（SnCl 3）Cl] 3和[RhL（CO）Cl] 4，其中L为手性吡啶基膦4-（二苯基膦基甲基）-2,2-二甲基合成了-5-（2-吡啶基）-1,3-二氧戊环，并通过IR，NMR和FAB质谱对其进行了表征。化合物1的结构X射线衍射已经解决了该问题：配体通过P和N原子配位形成一个七元环，该环采用椅子构象。主链的氢原子之一位于准原子位置上的钯原子上方2.72（3）Å。光谱证据也支持在化合物2和3中配体的螯合行为。讨论了铑（I）物种4中L配体的行为。
• (−)-(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane a new chiral ligand for enantioselective catalysis
  作者：Giorgio Chelucci、M.Antonietta Cabras、Carlo Botteghi、Mauro Marchetti

  DOI：10.1016/s0957-4166(00)86190-x

  日期：1994.3

  The title compound (PYDIPHOS) has been prepared by a ten reaction sequence from dimethyl L-(+)-tartrate and checked in the palladium-catalyzed asymmetric hydroesterification of styrene and in the nickel catalyzed asymmetric cross-coupling reaction of 1-phenylethyl magnesium bromide with vinylbromide.
• Synthesis of homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane: Use in asymmetric catalysis
  作者：Giorgio Chelucci、M.Antonietta Cabras、Carlo Botteghi、Carmen Basoli、Mauro Marchetti

  DOI：10.1016/0957-4166(96)00086-9

  日期：1996.3

  Homochiral pyridyl, bipyridyl and phosphino derivatives of 2,2-dimethyl-1,3-dioxolane were prepared from L-(+)-tartrate. These compounds were assessed in metal catalyzed asymmetric addition of diethylzinc to benzaldehyde, hydroformylation of styrene, hydrocarboethoxylation of styrene and allylic alkylation of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate. (C) 1996 Elsevier Science Ltd