dimethyl tert-butylphosphonate | 69404-42-8

• 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: dimethyl tert-butylphosphonate
• 英文别名: dimethyl tert-butylphosphonite；tert-butyl-phosphonic acid dimethyl ester；tert-Butyl-phosphonsaeure-dimethylester；2-Dimethoxyphosphoryl-2-methylpropane
• CAS: 69404-42-8
• 化学式: C₆H₁₅O₃P
• 分子量: 166.157
• InChiKey: MERNVKGUVJSUHN-UHFFFAOYSA-N

物化性质

• 沸点：
  193.5±9.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-η5-Cp(cobalt)(iodo)2(P(phenyl)2N(H)CH(methyl)phenyl) 、 dimethyl tert-butylphosphonate 以 二氯甲烷 为溶剂， 以24.2%的产率得到
  参考文献：
  名称：

  Diastereoselective Arbuzov dealkylation and evidence for phosphorus-carbon bond activation of prochiral cobalt(III) phosphonite complexes

  摘要：

  (S(c))-(eta5-CP)CoI2(PPh2NHC*H(Me)Ph) reacts with 1 equiv of dimethyl tert-butyl- or ethylphosphonite in methylene chloride solution to give diastereomeric 'P-chiral phosphinate Arbuzov products (R,S(Co),S(P);S(C))-(eta5-Cp)CoI(PPh2NHC*H(Me)Ph)(P(O)(OMe)(t-Bu)) (3a) and (R,S(Co),S(P);S(C))-(eta5-Cp)CoI(PPh2NHC*H(Me)Ph)(P(O)(OMe)(Et))(3b), respectively. Apparent phosphorus-carbon bond cleavage also occurs to give (R,S(Co);S(C))-(eta5-Cp)CoI(PPh2NHC*H(Me)-Ph)P(O)(OMe)2) (4), which was isolated in low yield after aerial workup. Two diastereomers of the tert-butyl series 3a and one diastereomer of the four isolated for the ethyl series 3b were characterized by single-crystal X-ray diffraction. (S(Co);R(P);S(C))-3a-1 crystallizes in the space group P2(1)2(1)2(1) with a = 9.815(4) angstrom, b = 14.314(6) angstrom, c = 21.120(9) angstrom, V = 2967(2) angstrom3, Z = 4, and RF = 2.83% for 5958 reflections (F > 4.0sigma(F)) at 198 K. (R(Co);S(P);S(C))-3a-2 crystallizes in the space group P2(1) with a = 13.073(5) angstrom, b = 8.731(2) angstrom, c = 13.537(5) angstrom, beta = 106.49(3)-degrees, V = 1481.5(9) angstrom3, Z = 2, and R(F) = 3.19 % for 4846 reflections (F > 4.0sigma(F)) at 198 K. (R(Co);S(P);S(C))-3b-2 crystallizes in the space group P2(1)2(1)2, with a = 8.7004(7) angstrom, b = 12.0769(18) angstrom, c = 27.490(3) angstrom, V = 2888.5(6) angstrom3, Z = 4, and R(F) = 4.4 % for 3118 reflections (F > 2.5sigma(F)) at 297 K. The absolute configurations of all diastereomers were assigned on the basis of crystallographic results, circular dichroism, and chemical cycles involving Co epimerization. P=O ... H-N intramolecular hydrogen bonding establishes a 'chaise longue'' conformation with pseudoaxial eta5-Cp and pseudoequatorial iodide in the solid state. Proton nuclear Overhauser difference (NOED) spectra show that the solid-state conformation is retained in solution. Optical yields increased with increasing steric demands of the prochiral phosphonite substituent. A model based on 1,3-diaxial steric interactions in the transition state leading to dealkylation is proposed to account for the observed Co --> P chiral induction.

  DOI：

  10.1021/om00032a029
• 作为产物：
  描述：

  methyl tert-butylphosphonochloridate 以 乙醚 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 dimethyl tert-butylphosphonate
  参考文献：
  名称：

  Dabkowski, Wojciech; Michalski, Jan; Skrzypczynski, Zbigniew, Chemische Berichte, 1985, vol. 118, # 5, p. 1809 - 1824

  摘要：

  DOI：

文献信息

• PRODRUGS OF NH-ACIDIC COMPOUNDS: ESTER, CARBONATE, CARBAMATE AND PHOSPHONATE DERIVATIVES
  申请人：Blumberg Laura Cook

  公开号：US20110319422A1

  公开（公告）日：2011-12-29

  The invention provides a method of sustained delivery of a lactam, imide, amide, sulfonamide, carbamate or urea containing parent drug by administering to a patient an effective amount of a prodrug compound of the invention wherein upon administration to the patient, release of the parent drug from the prodrug is sustained release. Prodrug compounds suitable for use in the methods of the invention are labile conjugates of parent drugs that are derivatized through carbonyl linked prodrug moieties. The prodrug compounds of the invention can be used to treat any condition for which the lactam, imide, amide, sulfonamide, carbamate or urea containing parent drug is useful as a treatment.

  该发明提供了一种持续释放内酰胺、亚酰胺、酰胺、磺胺、碳酸酯或尿素含有母药的方法，通过向患者施用该发明的一种前药化合物的有效量，在向患者施用后，从前药中释放母药是持续释放的。适用于该发明方法的前药化合物是母药的不稳定结合物，通过羰基连接的前药基团进行衍生化。该发明的前药化合物可用于治疗任何需要内酰胺、亚酰胺、酰胺、磺胺、碳酸酯或尿素含有母药作为治疗的情况。
• METHODS FOR TREATING ARENAVIRIDAE AND CORONAVIRIDAE VIRUS INFECTIONS
  申请人：Gilead Sciences, Inc.

  公开号：US20170071964A1

  公开（公告）日：2017-03-16

  Provided are methods for treating Arenaviridae and Coronaviridae virus infections by administering nucleosides and prodrugs thereof, of Formula I: wherein the 1′ position of the nucleoside sugar is substituted. The compounds, compositions, and methods provided are particularly useful for the treatment of Lassa virus and Junin virus infections.

  提供了通过给予核苷和其前药治疗Arenaviridae和Coronaviridae病毒感染的方法，其化学式为I： 其中核苷糖的1'位置被取代。所提供的化合物、组合物和方法特别适用于治疗拉沙病毒和胡宁病毒感染。
• 2' FLUORO SUBSTITUTED CARBA-NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT
  申请人：Gilead Sciences, Inc.

  公开号：US20170226140A1

  公开（公告）日：2017-08-10

  Provided are methods for treating Orthomyxoviridae virus infections by administering ribosides, riboside phosphates and prodrugs thereof, of Formula I: wherein R 2 is halogen. The compounds, compositions, and methods provided are particularly useful for the treatment of Human Influenza virus infections.

  提供了一种通过给予公式I中的核糖苷、核糖苷磷酸和其前药来治疗Orthomyxoviridae病毒感染的方法：其中R2是卤素。所提供的化合物、组合物和方法特别适用于治疗人类流感病毒感染。
• 2'-FLUORO SUBSTITUTED CARBA-NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT
  申请人：Cho Aesop

  公开号：US20110070194A1

  公开（公告）日：2011-03-24

  Provided are pyrrolo[1,2-f][1,2,4]triazinyl, imidazo[1,5-f][1,2,4]triazinyl, imidazo[1,2-f][1,2,4]triazinyl, and [1,2,4]triazolo[4,3-f][1,2,4]triazinyl nucleosides, nucleoside phosphates and prodrugs thereof, wherein the 2′ position of the nucleoside sugar is substituted with halogen and carbon substitutents. The compounds, compositions, and methods provided are useful for the treatment of Flaviviridae virus infections, particularly hepatitis C infections caused by both wild type and mutant strains of HCV.

  提供了吡咯并[1,2-f][1,2,4]三唑基，咪唑并[1,5-f][1,2,4]三唑基，咪唑并[1,2-f][1,2,4]三唑基，以及[1,2,4]三唑并[4,3-f][1,2,4]三唑基核苷，核苷酸磷酸酯和它们的前药，其中核苷糖的2'位置被卤素和碳取代基取代。提供的化合物、组合物和方法对于治疗黄病毒科病毒感染特别有效，尤其是治疗由HCV的野生型和突变株引起的丙型肝炎感染。
• CATALYSTS AND METHODS FOR POLYMER SYNTHESIS
  申请人：NOVOMER, INC.

  公开号：US20130144032A1

  公开（公告）日：2013-06-06

  The present invention provides unimolecular metal complexes having increased activity in the copolymerization of carbon dioxide and epoxides. Also provided are methods of using such metal complexes in the synthesis of polymers. According to one aspect, the present invention provides metal complexes comprising an activating species with co-catalytic activity tethered to a multidentate ligand that is coordinated to the active metal center of the complex.

  本发明提供了在二氧化碳和环氧化物的共聚合中具有增强活性的单分子金属配合物。还提供了使用这种金属配合物在合成聚合物中的方法。根据一个方面，本发明提供了包括与具有共催化活性的活化物种相耦合的多齿配体的金属配合物，该多齿配体与复合物的活性金属中心配位。