4-(Diphenylphosphinyl)-5-oxoheptan-2-one | 131904-22-8

• 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: 4-(Diphenylphosphinyl)-5-oxoheptan-2-one
• 英文别名: 4-diphenylphosphorylheptane-2,5-dione
• CAS: 131904-22-8
• 化学式: C₁₉H₂₁O₃P
• 分子量: 328.348
• InChiKey: ATQUJDOKVRNLOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(Diphenylphosphinyl)-5-oxoheptan-2-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以82%的产率得到5-(Diphenylphosphinyl)-2,3-dimethylcyclopent-2-en-1-one
  参考文献：
  名称：

  Methylenomycin B: new syntheses based on .beta.- and .gamma.-keto phosphonates and .gamma.-keto phosphine oxides

  摘要：

  Methylenomycin B has been synthesized from diethyl 2-oxobutanephosphonate (4) in three steps in 39% overall yield. Starting from diethyl 3-oxobutanephosphonate (10) and diphenyl(3-oxobutyl)phosphine oxide (13), methylenomycin B has been obtained in 34% and 27% overall yield, respectively. A characteristic feature of these syntheses of methylenomycin B is that the exo-methylene function is introduced via the Horner-Wittig reaction of formaldehyde (36% aqueous solution) with the corresponding alpha-phosphorylcyclopentenones 6 and 20. The latter were obtained from phosphorylated 1,4-diketones by intramolecular base-catalyzed cyclization. A brief discussion of some mechanistic aspects of the Conant reaction is also given.

  DOI：

  10.1021/jo00003a051
• 作为产物：
  描述：

  (3-oxobutyl)diphenylphosphine oxide 在 盐酸 、 N-氯代丁二酰亚胺 、 正丁基锂 、 二甲基硫 、 四甲基乙二胺 、 三乙胺 、 mercury dichloride 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 水 、 甲苯 、 苯 为溶剂， 反应 7.27h， 生成 4-(Diphenylphosphinyl)-5-oxoheptan-2-one
  参考文献：
  名称：

  Methylenomycin B: new syntheses based on .beta.- and .gamma.-keto phosphonates and .gamma.-keto phosphine oxides

  摘要：

  Methylenomycin B has been synthesized from diethyl 2-oxobutanephosphonate (4) in three steps in 39% overall yield. Starting from diethyl 3-oxobutanephosphonate (10) and diphenyl(3-oxobutyl)phosphine oxide (13), methylenomycin B has been obtained in 34% and 27% overall yield, respectively. A characteristic feature of these syntheses of methylenomycin B is that the exo-methylene function is introduced via the Horner-Wittig reaction of formaldehyde (36% aqueous solution) with the corresponding alpha-phosphorylcyclopentenones 6 and 20. The latter were obtained from phosphorylated 1,4-diketones by intramolecular base-catalyzed cyclization. A brief discussion of some mechanistic aspects of the Conant reaction is also given.

  DOI：

  10.1021/jo00003a051

文献信息

• MIKOLAJCZYK, MARIAN;ZATORSKI, ANDRZEJ, J. ORG. CHEM., 56,(1991) N, C. 1217-1223
  作者：MIKOLAJCZYK, MARIAN、ZATORSKI, ANDRZEJ

  DOI：——

  日期：——