2,2,2-trifluoroethyl phosphodichloridite | 103981-69-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 2,2,2-trifluoroethyl phosphodichloridite
• 英文别名: 2,2,2-trifluoroethyl dichlorophosphite；dichloro(2,2,2-trifluoroethoxy)phosphane
• CAS: 103981-69-7
• 化学式: C₂H₂Cl₂F₃OP
• 分子量: 200.912
• InChiKey: IXWSZOUBJKMCEM-UHFFFAOYSA-N

物化性质

• 沸点：
  103.6±40.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoroethyl phosphodichloridite 、 烯丙醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到diallyl (2,2,2-trifluoroethyl)phosphite
  参考文献：
  名称：

  Synthesis of Non-Symmetric Functionalized Polyfluoroalkyl Phosphites

  摘要：

  Two ways for the synthesis of new representatives of non-symmetric organic phosphites with polyfluoroalkyl substituents were developed based on organic dichlorophosphites. The reaction of polyfluoroalkyl dichlorophosphites with allyl alcohol, proceeding at a temperature of -10-22 degrees C (2 h) in the presence of triethylamine, gave diallyl polyfluoroalkyl phosphites in a yield of 75-77%. Under similar conditions (-30-22 degrees C, 2-4 h, Et3N), alkyl (or aryl) dichlorophosphites reacted with polyfluoroalkanols to form alkyl (or aryl) bis(polyfluoroalkyl) phosphites (yield 56-67%). Unlike diallylpolyfluoroalkyl- and alkylbis(polyfluoroalkyl) phosphites, arylbis(polyfluoroalkyl) phosphites are symmetrized under storage conditions (room temperature, inert atmosphere), forming the corresponding triaryl- and tris(polyfluoroalkyl) phosphites.

  DOI：

  10.1134/s1070363220050138
• 作为产物：
  描述：

  2,2,2-三氟乙醇 在 三乙胺 、 三氯化磷 作用下， 生成 2,2,2-trifluoroethyl phosphodichloridite
  参考文献：
  名称：

  多氟烷基二氯亚磷酸酯与炔丙醇的反应：多氟烷基二（2-丙炔基）亚磷酸酯的合成和异构化

  摘要：

  多氟烷基二氯亚磷酸酯与炔丙醇在 Et 3 N/己烷中反应生成二(2-丙炔基)多氟烷基亚磷酸酯，其在储存时转化为多氟烷基2-丙炔基烯基膦酸酯和异构体(1-丙炔基)膦酸酯。

  DOI：

  10.1007/s11172-021-3332-y

文献信息

• Synthesis and separation of diastereomers of <i>O</i>-(2,2,2-trifluoroethyl)-3′,5′-dinucleoside phosphates
  作者：Weide Luo、Elena Atrazheva、Nancy Fregeau、William H. Gmeiner、J. William Lown

  DOI：10.1139/v94-193

  日期：1994.6.1

  The synthesis, diastereomeric separation, and characterization are described for a series of novel O-(2,2,2-trifluoroethyl)-3′,5′-dinucleoside phosphates, required for incorporation into antisense probes in the magnetic resonance imaging investigation of biodistribution. Preliminary assignment of the absolute configuration of the Rp and Sp diastereomers is made on the basis of 31 P NMR spectra.

  描述了一系列新型 O-(2,2,2-三氟乙基)-3',5'-双核苷磷酸酯的合成、非对映体分离和表征，在生物分布的磁共振成像研究中需要纳入反义探针. Rp 和 Sp 非对映异构体的绝对构型的初步分配是基于 31 P NMR 光谱进行的。
• Konovalova, I.V.; Burnaeva, L.A.; Loginova, I.V., Journal of general chemistry of the USSR, 1991, vol. 61, # 11.1, p. 2298 - 2302
  作者：Konovalova, I.V.、Burnaeva, L.A.、Loginova, I.V.、Pudovik, A.N.

  DOI：——

  日期：——
• Synthesis of Amido- and Diamidophosphites with Polyfluoroalkyl Substituents
  作者：S. F. Malysheva、N. K. Gusarova、N. A. Belogorlova、A. M. Nalibayeva、S. V. Yasko、N. A. Chernysheva、S. I. Verkhoturova、G. K. Bishimbayeva、B. A. Trofimov

  DOI：10.1134/s1070363220020103

  日期：2020.2

  Bis(polyfluoroalkyl) chlorophosphites and polyfluoroalkyl dichlorophosphites react easily with secondary amines (from -40 to -22 degrees C, 1-3 h, CH2Cl2) in the presence or absence of triethylamine to form the corresponding bis(polyfluoroalkyl) diorganylamidophosphites or bis(diorganylamido) polyfluoroalkyl phosphites in the yield of up to 74%. Bis(polyfluoroalkyl) diorganylamidophosphites were also synthesized from diorganylamidodichlorophosphites and polyfluoroalkanols (-25 to -22 degrees C, 2 h, Et3N-CH2Cl2) with a yield of 56-60%.
• MAHMOOD T.; SHREEVE J. M., INORG. CHEM., 25,(1986) N 21, 3830-3837
  作者：MAHMOOD T.、 SHREEVE J. M.

  DOI：——

  日期：——
• Synthesis of Non-Symmetric Functionalized Polyfluoroalkyl Phosphites
  作者：N. K. Gusarova、S. F. Malysheva、N. A. Belogorlova、S. I. Verkhoturova、L. A. Oparina、S. N. Arbuzova、N. A. Chernysheva、A. M. Nalibayeva、G. K. Bishimbayeva、S. V. Yas’ko、B. A. Trofimov

  DOI：10.1134/s1070363220050138

  日期：2020.5

  Two ways for the synthesis of new representatives of non-symmetric organic phosphites with polyfluoroalkyl substituents were developed based on organic dichlorophosphites. The reaction of polyfluoroalkyl dichlorophosphites with allyl alcohol, proceeding at a temperature of -10-22 degrees C (2 h) in the presence of triethylamine, gave diallyl polyfluoroalkyl phosphites in a yield of 75-77%. Under similar conditions (-30-22 degrees C, 2-4 h, Et3N), alkyl (or aryl) dichlorophosphites reacted with polyfluoroalkanols to form alkyl (or aryl) bis(polyfluoroalkyl) phosphites (yield 56-67%). Unlike diallylpolyfluoroalkyl- and alkylbis(polyfluoroalkyl) phosphites, arylbis(polyfluoroalkyl) phosphites are symmetrized under storage conditions (room temperature, inert atmosphere), forming the corresponding triaryl- and tris(polyfluoroalkyl) phosphites.