1-(Diphenylphosphinyl)butan-3-one ethylene ketal | 69803-55-0

• 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: 1-(Diphenylphosphinyl)butan-3-one ethylene ketal
• 英文别名: 4-diphenylphosphinoylbutan-2-one ethylene acetal；[2-(2-Methyl-1,3-dioxolan-2-yl)ethyl](oxo)diphenyl-lambda~5~-phosphane；2-(2-diphenylphosphorylethyl)-2-methyl-1,3-dioxolane
• CAS: 69803-55-0
• 化学式: C₁₈H₂₁O₃P
• 分子量: 316.337
• InChiKey: PTUDKLAXYLUHHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(Diphenylphosphinyl)butan-3-one ethylene ketal 在 盐酸 、 sodium hydroxide 、 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 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 反应 7.27h， 生成 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 、 乙二醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 6.0h， 以100%的产率得到1-(Diphenylphosphinyl)butan-3-one ethylene ketal
  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

• Bell, Andrew; Davidson, Alan H.; Earnshaw, Chris, Journal of the Chemical Society. Perkin transactions I, 1983, # 12, p. 2879 - 2892
  作者：Bell, Andrew、Davidson, Alan H.、Earnshaw, Chris、Norrish, Howard K.、Torr, Richard S.、et al.

  DOI：——

  日期：——
• Earnshaw, Chris; Torr, Richard S.; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1983, # 12, p. 2893 - 2902
  作者：Earnshaw, Chris、Torr, Richard S.、Warren, Stuart

  DOI：——

  日期：——
• Cristau, Henri-Jean; Torreilles, Eliane; Barois-Gacherieu, Catherine, Synthetic Communications, 1988, vol. 18, # 2, p. 185 - 190
  作者：Cristau, Henri-Jean、Torreilles, Eliane、Barois-Gacherieu, Catherine

  DOI：——

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

  DOI：——

  日期：——
• EARNSHAW, C.;TORR, R. S.;WARREN, S., J. CHEM. SOC. PERKIN TRANS., 1983, N 12, 2893-2901
  作者：EARNSHAW, C.、TORR, R. S.、WARREN, S.

  DOI：——

  日期：——