1-Hydroxy-3-methyl-2-phospholenoxid | 3858-24-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 1-Hydroxy-3-methyl-2-phospholenoxid
• 英文别名: 2-Phospholene, 1-hydroxy-3-methyl-, 1-oxide；1-hydroxy-4-methyl-2,3-dihydro-1λ5-phosphole 1-oxide
• CAS: 3858-24-0
• 化学式: C₅H₉O₂P
• 分子量: 132.099
• InChiKey: IZGYVCZECHLMBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Hydroxy-3-methyl-2-phospholenoxid 在 二苯基硅烷 作用下， 生成 3-Methyl-Δ²-phospholin
  参考文献：
  名称：

  Fritzsche,H. et al., Chemische Berichte, 1965, vol. 98, p. 1681 - 1687

  摘要：

  DOI：
• 作为产物：
  描述：

  1-ethoxy-3-methyl-2,5-dihydro-1H-phosphole 1-oxide 在 盐酸 、 水 作用下， 生成 1-Hydroxy-3-methyl-2-phospholenoxid 、 1-hydroxy-3-methyl-3-phospholene 1-oxide
  参考文献：
  名称：

  次膦酸盐和膦酸盐的水解和醇解

  摘要：

  摘要 次膦酸和膦酸有用的中间体和生物活性化合物可以分别由它们的酯制备：次膦酸盐和膦酸盐，通过酸催化水解在常规加热或MW照射下进行。烷基次膦酸盐的酯交换反应仅在合适的离子液体作为催化剂存在的情况下进行。在苯基膦酸盐的情况下，取决于离子液体的性质，酯的形成伴随着 C-O 键的裂变。

  DOI：

  10.1080/10426507.2021.1991345

文献信息

• A study on the acidic hydrolysis of cyclic phosphinates: 1-Alkoxy-3-phospholene 1-oxides, 1-ethoxy-3-methylphospholane 1-oxide, and 1-ethoxy-3-methyl-1,2,3,4,5,6-hexahydrophosphinine 1-oxide
  作者：György Keglevich、Zita Rádai、Nikoletta Harsági、Áron Szigetvári、Nóra Zsuzsa Kiss

  DOI：10.1002/hc.21394

  日期：2017.9

  AbstractThe hydrochloric acid‐catalyzed hydrolysis of phosphinates was studied on 1‐alkoxy‐3‐phospholene 1‐oxides, 1‐ethoxy‐3‐methylphospholane 1‐oxide, and 1‐ethoxy‐3‐methyl‐1,2,3,4,5,6‐hexahydrophosphinine 1‐oxide as the model compounds. Under the conditions applied, the isomerization of the 3‐phospholene moiety to the 2‐phospholene ring also occurred leading to mixtures of the corresponding 1‐hydroxy‐3‐phospholene oxide and 1‐hydroxy‐2‐phospholene oxide. According to our optimized method, using 3 equivalents (0.5 mL) of concentrated hydrochloric acid in 1 mL of water per ca. 2 mmol of the substrate at reflux, the completion required 3‐10 hour. The hydrolyses were characterized by pseudo‐first‐order rate constants and the isomerizations by rate constants. The application of p‐toluenesulfonic acid under microwave irradiation at 140°C in the hydrolysis of 1‐alkoxy‐3‐methyl‐3‐phospholene oxides associated with reaction times of 1‐3 hour. The reactivity order of the 5‐ and 6‐ring phosphinates in hydrolysis was set up.
• Fritzsche,H. et al., Chemische Berichte, 1965, vol. 98, p. 1681 - 1687
  作者：Fritzsche,H. et al.

  DOI：——

  日期：——
• Hydrolysis and alcoholysis of phosphinates and phosphonates
  作者：Nikoletta Harsági、Betti Szőllősi、Petra Regina Varga、György Keglevich

  DOI：10.1080/10426507.2021.1991345

  日期：2022.6.3

  Abstract Phosphinic and phosphonic acids useful intermediates and biologically active compounds may be prepared from their esters: phosphinates and phosphonates, respectively, by acid-catalyzed hydrolysis either on conventional heating or on MW irradiation. The transesterification of alkyl phosphinates took place only in the presence of suitable ionic liquids as the catalysts. In the cases of phenylphosphonates

  摘要 次膦酸和膦酸有用的中间体和生物活性化合物可以分别由它们的酯制备：次膦酸盐和膦酸盐，通过酸催化水解在常规加热或MW照射下进行。烷基次膦酸盐的酯交换反应仅在合适的离子液体作为催化剂存在的情况下进行。在苯基膦酸盐的情况下，取决于离子液体的性质，酯的形成伴随着 C-O 键的裂变。