2-Diethoxyphosphoryl-1-(furan-3-yl)prop-2-en-1-ol | 913199-09-4

• 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: 2-Diethoxyphosphoryl-1-(furan-3-yl)prop-2-en-1-ol
• CAS: 913199-09-4
• 化学式: C₁₁H₁₇O₅P
• 分子量: 260.227
• InChiKey: ZWHLKTVPBBTYKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Diethoxyphosphoryl-1-(furan-3-yl)prop-2-en-1-ol 在 三氯化铁 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 3.0h， 生成 5,6-Dichloro-2-[2-diethoxyphosphoryl-1-(furan-3-yl)prop-2-enyl]isoindole-1,3-dione
  参考文献：
  名称：

  Phosphine-Catalyzed Allylic Substitution of Morita−Baylis−Hillman Acetates:  Synthesis of N-Protected β-Aminophosphonic Acid Esters

  摘要：

  A series of N-protected beta-amino phosphonic acid esters have been prepared by phosphine-catalyzed allylic substitution of 2-(diethylphosphonyl)-substituted allylic acetates employing 4,5-dichlorophthalimide as nucleophilic partner. These organocatalytic allylic substitutions exhibit exceptionally high levels of regiospecificity by virtue of a tandem S(N)2'-S(N)2' mechanism.

  DOI：

  10.1021/jo061218s
• 作为产物：
  描述：

  3-糠醛 、 乙烯基磷酸二乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以74%的产率得到2-Diethoxyphosphoryl-1-(furan-3-yl)prop-2-en-1-ol
  参考文献：
  名称：

  Phosphine-Catalyzed Allylic Substitution of Morita−Baylis−Hillman Acetates:  Synthesis of N-Protected β-Aminophosphonic Acid Esters

  摘要：

  A series of N-protected beta-amino phosphonic acid esters have been prepared by phosphine-catalyzed allylic substitution of 2-(diethylphosphonyl)-substituted allylic acetates employing 4,5-dichlorophthalimide as nucleophilic partner. These organocatalytic allylic substitutions exhibit exceptionally high levels of regiospecificity by virtue of a tandem S(N)2'-S(N)2' mechanism.

  DOI：

  10.1021/jo061218s

文献信息

• Phosphine-Catalyzed Allylic Substitution of Morita−Baylis−Hillman Acetates:  Synthesis of N-Protected β-Aminophosphonic Acid Esters
  作者：HaeIl Park、Chang-Woo Cho、Michael J. Krische

  DOI：10.1021/jo061218s

  日期：2006.9.1

  A series of N-protected beta-amino phosphonic acid esters have been prepared by phosphine-catalyzed allylic substitution of 2-(diethylphosphonyl)-substituted allylic acetates employing 4,5-dichlorophthalimide as nucleophilic partner. These organocatalytic allylic substitutions exhibit exceptionally high levels of regiospecificity by virtue of a tandem S(N)2'-S(N)2' mechanism.