ethyl 2-hydroxyethyl H-phosphonate | 21941-54-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: ethyl 2-hydroxyethyl H-phosphonate
• 英文别名: 2-[Ethoxy(oxido)phosphaniumyl]oxyethanol
• CAS: 21941-54-8
• 化学式: C₄H₁₁O₄P
• 分子量: 154.103
• InChiKey: CWNKZYJXVMMZGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙氧基-1,3,2-二氧杂磷杂环戊烷 在 水 作用下， 生成 ethyl 2-hydroxyethyl H-phosphonate
  参考文献：
  名称：

  Arbusow; Soroastrowa; Rispoloshenski, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1948, p. 208

  摘要：

  DOI：

文献信息

• Studies on Reactions of Nucleoside H-Phosphonates with Bifunctional Reagents. Part VI. Reaction with Diols
  作者：Michal Sobkowski、Malgorzata Wenska、Adam Kraszewski、Jacek Stawiński

  DOI：10.1080/15257770008045441

  日期：2000.10

  types of condensing agents have been studied. Depending on the coupling procedure and the length of a polymethylene chain of the diol, acyclic H-phosphonate diesters or cyclic phosphite triesters were formed. The course of oxidation with iodine to produce cyclic nucleoside alkyl phosphotriesters or hydroxyalkyl nucleoside phosphodiesters can be controlled by the amount of water present in the reaction

  摘要研究了不同类型的缩合剂对核苷H-膦酸酯与各种二醇的反应。取决于偶联过程和二醇的多亚甲基链的长度，形成无环的H-膦酸酯二酯或环状的亚磷酸酯三酯。用碘氧化产生环状核苷烷基磷酸三酯或羟烷基核苷磷酸二酯的过程可以通过反应介质中存在的水量来控制。
• Microwave-assisted alcoholysis of dialkyl <i>H</i>-phosphonates by diols and amino alcohols
  作者：Ádám Tajti、György Keglevich、Erika Bálint

  DOI：10.1080/10426507.2017.1284841

  日期：2017.6.3

  GRAPHICAL ABSTRACT ABSTRACT The microwave-assisted alcoholysis of dialkyl H-phosphonates with diols and amino alcohols aiming at P-functionalized monomers was studied. Depending on the conditions (molar ratio, temperature, time), the reaction could be fine-tuned to afford the target mono and bis hydroxyalkyl or aminoalkyl H-phopshonate derivatives. The formation of three types of by-products was also

  图形摘要 摘要 针对 P 官能化单体，研究了 H-膦酸二烷基酯与二醇和氨基醇的微波辅助醇解。根据条件（摩尔比、温度、时间），可以对反应进行微调以提供目标单和双羟烷基或氨基烷基 H-膦酸酯衍生物。还研究了三种副产物的形成。热成就显示酯交换的效率较低。
• Nucleophilic transformations of cyclic phosphate triesters
  作者：Nissan Ashkenazi、Yishai Karton、Yoffi Segall

  DOI：10.1016/j.tetlet.2004.09.011

  日期：2004.10

  Reactions of cyclic phosphate triesters, such as 2-ethoxy-1,3,2-dioxaphospholane 2-oxide, with Grignard reagents such as phenyl-, alkyl-, ethynyl-, and allyl-magnesium halides result in ring opening leading to the corresponding phosphonates, via nucleophilic attack of carbon on the phosphorus atom. Treatment of 2-ethoxy-1,3,2-dioxaphospholane 2-oxide with sodium borohydride yields ethyl 2-hydroxyethyl

  环状磷酸三酯（例如2-乙氧基-1,3,2-二氧杂磷杂环戊烷2氧化物）与Grignard试剂（例如苯基卤，烷基卤，乙炔基卤和烯丙基镁卤化物）的反应会导致开环，从而导致相应的反应。通过碳对磷原子的亲核攻击而生成膦酸酯。用硼氢化钠处理2-乙氧基-1,3,2-二氧杂膦烷2-氧化物得到2-羟乙基亚磷酸乙酯。该反应仅适用于五元环系统：在这些条件下，无环磷酸三酯（如磷酸三乙酯）不发生反应，类似的六元环系统2-乙氧基-1,3,2-二氧杂磷杂环丁烷2-氧化物反应仅部分产生未鉴定的磷酸酯和痕量的膦酸酯产物。两种化合物均对NaBH 4呈惰性。
• Ambident Electrophilicity of 5-Membered Ring Phosphate Triesters
  作者：Nissan Ashkenazi、Yoffi Segall、Yishai Karton、Sanjio S. Zade、Michael Bendikov

  DOI：10.1080/10426500701735452

  日期：2008.1.14

  The reactions of 2-alkoxy-1,3,2-dioxaphospholane 2-oxide with various nucleophiles were studied both experimentally and theoretically. These studies show that 5-membered ring phosphate triesters act as ambident electrophiles: hard and bulky nucleophiles attack at the phosphorus while soft nucleophiles attack at the ring carbon.
• Gefter, Zhurnal Obshchei Khimii, 1956, vol. 26, p. 1440;engl.Ausg.S.1619
  作者：Gefter

  DOI：——

  日期：——