diisopropyl (E)-1-[hydroxy(phenyl)methyl]-3,3-dimethyl-1-butenylphosphonate | 417712-16-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diisopropyl (E)-1-[hydroxy(phenyl)methyl]-3,3-dimethyl-1-butenylphosphonate
• 英文别名: (E)-4,4-dimethyl-2-[oxido-di(propan-2-yloxy)phosphaniumyl]-1-phenylpent-2-en-1-ol
• CAS: 417712-16-4
• 化学式: C₁₉H₃₁O₄P
• 分子量: 354.426
• InChiKey: JCBBMBLNQIMLTK-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diisopropyl (E)-1-[hydroxy(phenyl)methyl]-3,3-dimethyl-1-butenylphosphonate 在 potassium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.58h， 生成 (6,6-dimethyl-3,4-heptadienyl)benzene
  参考文献：
  名称：

  Synthesis of allenes by double Horner–Wadsworth–Emmons reaction

  摘要：

  LDA treatment of aldehydes or ketone with alkenylphosphonates 2, prepared by Horner-Wadsworth-Emmons (HWE) reaction of methylenebisphosphonate I with aldehydes, afforded Baylis-Hillman reaction-type products 5 in high yields. HWE olefination of 5 with KH or KH-18-crown-6 as a base provided allenes in good yields. One-flask procedure was successfully developed starting from I to afford an allene in a reasonably good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01089-4
• 作为产物：
  描述：

  亚甲基二磷酸四异丙酯 在 sodium hydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 生成 diisopropyl (E)-1-[hydroxy(phenyl)methyl]-3,3-dimethyl-1-butenylphosphonate
  参考文献：
  名称：

  Synthesis of allenes by double Horner–Wadsworth–Emmons reaction

  摘要：

  LDA treatment of aldehydes or ketone with alkenylphosphonates 2, prepared by Horner-Wadsworth-Emmons (HWE) reaction of methylenebisphosphonate I with aldehydes, afforded Baylis-Hillman reaction-type products 5 in high yields. HWE olefination of 5 with KH or KH-18-crown-6 as a base provided allenes in good yields. One-flask procedure was successfully developed starting from I to afford an allene in a reasonably good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01089-4

文献信息

• Allenes through Horner-Wadsworth-Emmons Olefination of Alkenylphosphonates
  作者：Yasuo Nagaoka、Hideki Inoue、Kiyoshi Tomioka

  DOI：10.1080/10426500212268

  日期：2002.6.1

  Mono- and di-substituted allenes 5 were synthesized by successive Horner-Wadsworth-Emmons olefination starting from methylene-bisphosphonate 1 and two carbonyl compounds. The key to success is KH or KH-18-crown-6 as a base for the second HWE olefination of hydroxyalkenylphosphonates 4 .

  单取代和双取代的丙二烯 5 是通过从亚甲基双膦酸酯 1 和两个羰基化合物开始的连续霍纳-沃兹沃思-埃蒙斯烯化合成的。成功的关键是 KH 或 KH-18-crown-6 作为羟基烯基膦酸酯 4 的第二次 HWE 烯化的基础。
• Synthesis of allenes by double Horner–Wadsworth–Emmons reaction
  作者：Hideki Inoue、Hiroshi Tsubouchi、Yasuo Nagaoka、Kiyoshi Tomioka

  DOI：10.1016/s0040-4020(01)01089-4

  日期：2002.1

  LDA treatment of aldehydes or ketone with alkenylphosphonates 2, prepared by Horner-Wadsworth-Emmons (HWE) reaction of methylenebisphosphonate I with aldehydes, afforded Baylis-Hillman reaction-type products 5 in high yields. HWE olefination of 5 with KH or KH-18-crown-6 as a base provided allenes in good yields. One-flask procedure was successfully developed starting from I to afford an allene in a reasonably good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.