2-ethoxy-4H-benzo[1,3,2]dioxaphosphorin-2-yl | 87451-61-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 2-ethoxy-4H-benzo[1,3,2]dioxaphosphorin-2-yl
• 英文别名: Saligeninphosphorigesaeureethylester；2-ethoxy-4H-1,3,2-benzodioxaphosphinine
• CAS: 87451-61-4
• 化学式: C₉H₁₁O₃P
• 分子量: 198.158
• InChiKey: WPQLFVWMDDKTQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethoxy-4H-benzo[1,3,2]dioxaphosphorin-2-yl 以 氘代氯仿 为溶剂， 生成 2-ethoxy-3H-benzo[d][1,2]oxaphosphole 2-oxide
  参考文献：
  名称：

  Formation of Benzooxaphosphole Oxide Heterocyclic System by the Ring-Contractive Arbuzov-Michaelis Isomerization of Alkoxy-Substituted Benzodioxaphosphorins

  摘要：

  A possibility of the Arbuzov-Michaelis-type isomerization is revealed for the model 2-ethoxy derivative 4 of the six-membered 4H-benzo[1,3,2]dioxaphosphorin heterocycle. The reaction proceeds with ring contraction to give the five-membered 3H-benzo[d][1,2]oxaphosphole 2-oxide heterocyclic system. Some synthetic possibilities of the new reaction disclosed here are demonstrated by introducing a pharmacophoric 5-O-nucleoside to the P(IV) atom leading to the 3H-benzo[d][1,2]oxaphosphole 2-oxide system by this new rearrangement reaction.

  DOI：

  10.1080/10426500210234
• 作为产物：
  描述：

  乙醇 、 2-chloro-4H-1,3,2-benzodioxaphosphorin 在 三乙胺 作用下， 以 Petroleum ether 为溶剂， 以44%的产率得到2-ethoxy-4H-benzo[1,3,2]dioxaphosphorin-2-yl
  参考文献：
  名称：

  Formation of Benzooxaphosphole Oxide Heterocyclic System by the Ring-Contractive Arbuzov-Michaelis Isomerization of Alkoxy-Substituted Benzodioxaphosphorins

  摘要：

  A possibility of the Arbuzov-Michaelis-type isomerization is revealed for the model 2-ethoxy derivative 4 of the six-membered 4H-benzo[1,3,2]dioxaphosphorin heterocycle. The reaction proceeds with ring contraction to give the five-membered 3H-benzo[d][1,2]oxaphosphole 2-oxide heterocyclic system. Some synthetic possibilities of the new reaction disclosed here are demonstrated by introducing a pharmacophoric 5-O-nucleoside to the P(IV) atom leading to the 3H-benzo[d][1,2]oxaphosphole 2-oxide system by this new rearrangement reaction.

  DOI：

  10.1080/10426500210234

文献信息

• Formation of Benzooxaphosphole Oxide Heterocyclic System by the Ring-Contractive Arbuzov-Michaelis Isomerization of Alkoxy-Substituted Benzodioxaphosphorins
  作者：Eduard E. Nifantiev、Svetlana B. Khrebtova、Yulia V. Kulikova、Dmitrii A. Predvoditelv、Tat′yana S. Kukhareva、Pavel V. Petrovskii、Mirjam Rose、Chris Meier

  DOI：10.1080/10426500210234

  日期：2002.1.1

  A possibility of the Arbuzov-Michaelis-type isomerization is revealed for the model 2-ethoxy derivative 4 of the six-membered 4H-benzo[1,3,2]dioxaphosphorin heterocycle. The reaction proceeds with ring contraction to give the five-membered 3H-benzo[d][1,2]oxaphosphole 2-oxide heterocyclic system. Some synthetic possibilities of the new reaction disclosed here are demonstrated by introducing a pharmacophoric 5-O-nucleoside to the P(IV) atom leading to the 3H-benzo[d][1,2]oxaphosphole 2-oxide system by this new rearrangement reaction.