Dimethyl 4-oxopentan-2-yl phosphite | 137837-43-5

• 分子结构分类: 有机化合物 - 有机磷化合物 - 亚磷酸三烷基酯
• 英文名称: Dimethyl 4-oxopentan-2-yl phosphite
• 英文别名: dimethyl 4-oxopentan-2-yl phosphite
• CAS: 137837-43-5
• 化学式: C₇H₁₅O₄P
• 分子量: 194.167
• InChiKey: CVLCMLLEVGZLBY-UHFFFAOYSA-N

物化性质

• 沸点：
  211.2±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethyl 4-oxopentan-2-yl phosphite 在 水 作用下， 生成 (2S*,3R*,5R*)-2-methoxy-3,5-dimethyl-2-oxo-1,2-oxa-phospholan-3-ol
  参考文献：
  名称：

  Stereochemistry of 1,2-oxaphospholanes. Part X. Synthesis, X-ray structure and NMR spectroscopy of (2S*,3R*,5R*)-2-methoxy-3,5-dimethyl-2-oxo-1,2-oxaphospholan-3-ol

  摘要：

  The title compound (4a) was synthesized from a phosphite compound obtained from 4-hydroxy-2-pentanone and dimethylphosphorochloridite, after addition of an equivalent of water. The cis-configuration of the P = O and C3-OH groups was established based on P-31 NMR chemical shifts. In chloroform, as well as in benzene solution, the most favorable conformations of the title compound are 5(4)T, 4E, and 3(4)T. The crystal and molecular structure of 4a has been determined by single-crystal X-ray diffraction data, and refined to R = 0.056. The five-membered ring has an envelope 4E (C(s)) conformation, with the asymmetry parameter-DELTA-C(s)(4) = 3.5-degrees. Both the C5-CH3 and the C3-CH3 groups are equatorial. In the solid state, the molecules form dimers with hydrogen bonding between the hydroxyl groups and the phosphoryl oxygen atom of an adjacent molecule. A quantitative comparison of the structure of 4a with the structure of the related 2-methoxy-3,5,5-trimethyl-2-oxo-1,2-oxaphosphospholan-3-ol is given.

  DOI：

  10.1007/bf01161080
• 作为产物：
  描述：

  4-羟基戊烷-2-酮 、 氯-二甲氧基膦 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 Dimethyl 4-oxopentan-2-yl phosphite
  参考文献：
  名称：

  Stereochemistry of 1,2-oxaphospholanes. Part X. Synthesis, X-ray structure and NMR spectroscopy of (2S*,3R*,5R*)-2-methoxy-3,5-dimethyl-2-oxo-1,2-oxaphospholan-3-ol

  摘要：

  The title compound (4a) was synthesized from a phosphite compound obtained from 4-hydroxy-2-pentanone and dimethylphosphorochloridite, after addition of an equivalent of water. The cis-configuration of the P = O and C3-OH groups was established based on P-31 NMR chemical shifts. In chloroform, as well as in benzene solution, the most favorable conformations of the title compound are 5(4)T, 4E, and 3(4)T. The crystal and molecular structure of 4a has been determined by single-crystal X-ray diffraction data, and refined to R = 0.056. The five-membered ring has an envelope 4E (C(s)) conformation, with the asymmetry parameter-DELTA-C(s)(4) = 3.5-degrees. Both the C5-CH3 and the C3-CH3 groups are equatorial. In the solid state, the molecules form dimers with hydrogen bonding between the hydroxyl groups and the phosphoryl oxygen atom of an adjacent molecule. A quantitative comparison of the structure of 4a with the structure of the related 2-methoxy-3,5,5-trimethyl-2-oxo-1,2-oxaphosphospholan-3-ol is given.

  DOI：

  10.1007/bf01161080

文献信息

• Stereochemistry of 1,2-oxaphospholanes. Part X. Synthesis, X-ray structure and NMR spectroscopy of (2S*,3R*,5R*)-2-methoxy-3,5-dimethyl-2-oxo-1,2-oxaphospholan-3-ol
  作者：A. E. Wróblewski、W. T. Konieczko、J. Skoweranda、M. Bukowska-Strzyżewska

  DOI：10.1007/bf01161080

  日期：1991.10

  The title compound (4a) was synthesized from a phosphite compound obtained from 4-hydroxy-2-pentanone and dimethylphosphorochloridite, after addition of an equivalent of water. The cis-configuration of the P = O and C3-OH groups was established based on P-31 NMR chemical shifts. In chloroform, as well as in benzene solution, the most favorable conformations of the title compound are 5(4)T, 4E, and 3(4)T. The crystal and molecular structure of 4a has been determined by single-crystal X-ray diffraction data, and refined to R = 0.056. The five-membered ring has an envelope 4E (C(s)) conformation, with the asymmetry parameter-DELTA-C(s)(4) = 3.5-degrees. Both the C5-CH3 and the C3-CH3 groups are equatorial. In the solid state, the molecules form dimers with hydrogen bonding between the hydroxyl groups and the phosphoryl oxygen atom of an adjacent molecule. A quantitative comparison of the structure of 4a with the structure of the related 2-methoxy-3,5,5-trimethyl-2-oxo-1,2-oxaphosphospholan-3-ol is given.