trans-2-Phenoxy-4-methyl-1,3,2λ³-dioxaphosphorinane | 3766-75-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-2-Phenoxy-4-methyl-1,3,2λ³-dioxaphosphorinane
• 英文别名: trans-2-phenoxy-4-methyl-1,3,2-dioxaphosphorinane；(2R,4R)-4-methyl-2-phenoxy-1,3,2-dioxaphosphinane
• CAS: 3766-75-4；142765-07-9
• 化学式: C₁₀H₁₃O₃P
• 分子量: 212.185
• InChiKey: WPFJXOHADQKQCV-YMTOWFKASA-N

物化性质

• 沸点：
  125-130 °C(Press: 8 Torr)
• 密度：
  1.178 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  trans-2-Phenoxy-4-methyl-1,3,2λ³-dioxaphosphorinane 在 diethoxyoxophosphoranesulfenyl chloride 作用下， 以 二氯甲烷 为溶剂， 生成 2-Phenoxy-4-methyl-1,3-dioxathiophosphorinan-2
  参考文献：
  名称：

  Reaction of tricoordinate phosphorus compounds with organophosphorus pseudohalogens. 1. Desulfurization and deoxygenation of oxophosphoranesulfenyl chlorides. Scope and mechanism

  摘要：

  The reaction of oxophosphoranesulfenyl chlorides RR'P(O)SCl 2 with P(III) compounds has been investigated. Its mechanistic features have been elucidated by variable-temperature P-31 NMR spectroscopy and stereochemical changes at P(IV) and P(III) phosphorus centers. These studies show that in all cases phosphonium intermediates containing the sulfur bridge >P(O)-S-P+ less than or similar to Cl- are formed. Depending on electronic and steric factors and reaction conditions, this primary phosphonium salt either decomposes by nucleophilic attack of the chloride counterion on the phosphoryl center (desulfurization pathway) or is transformed into the isomeric phosphonium salt >P(S)-O-P+ less than or similar to Cl-. The latter decomposes by the attack of the chloride anion on the thiophosphoryl center (deoxygenation pathway). P-31 NMR studies fully corroborated the observed stereochemical changes.

  DOI：

  10.1021/jo00044a035
• 作为产物：
  描述：

  trans-2-chloro-4-methyl-1,3,2-dioxaphosphorinane 、 苯酚 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 4-methyl-1,3,2-dioxaphosphinan-2-ium 2-oxide 、 trans-2-Phenoxy-4-methyl-1,3,2λ³-dioxaphosphorinane
  参考文献：
  名称：

  Synthesis and Conformational Analysis of Six-Membered Cyclic Phenyl Phosphites

  摘要：

  A procedure for synthesizing potentially anancomeric equatorial phenyl phosphites (cis-l and eq-cis-2) is reported. Spectral characteristics and low-temperature NMR studies on the phenyl phosphites suggest that eq-cis-a is a system with a predominant chair conformation in solution. On the contrary, cis-l is conformationally heterogeneous.

  DOI：

  10.1021/jo00121a041

文献信息

• Borisov, E. V.; Akhlebinin, A. K.; Nifant'ev, E. E., Journal of general chemistry of the USSR, 1984, vol. 54, # 10, p. 2096 - 2100
  作者：Borisov, E. V.、Akhlebinin, A. K.、Nifant'ev, E. E.

  DOI：——

  日期：——
• Reaction of tricoordinate phosphorus compounds with organophosphorus pseudohalogens. 1. Desulfurization and deoxygenation of oxophosphoranesulfenyl chlorides. Scope and mechanism
  作者：E. Krawczyk、J. Mikolajczak、A. Skowronska、J. Michalski

  DOI：10.1021/jo00044a035

  日期：1992.8

  The reaction of oxophosphoranesulfenyl chlorides RR'P(O)SCl 2 with P(III) compounds has been investigated. Its mechanistic features have been elucidated by variable-temperature P-31 NMR spectroscopy and stereochemical changes at P(IV) and P(III) phosphorus centers. These studies show that in all cases phosphonium intermediates containing the sulfur bridge >P(O)-S-P+ less than or similar to Cl- are formed. Depending on electronic and steric factors and reaction conditions, this primary phosphonium salt either decomposes by nucleophilic attack of the chloride counterion on the phosphoryl center (desulfurization pathway) or is transformed into the isomeric phosphonium salt >P(S)-O-P+ less than or similar to Cl-. The latter decomposes by the attack of the chloride anion on the thiophosphoryl center (deoxygenation pathway). P-31 NMR studies fully corroborated the observed stereochemical changes.
• Synthesis and Conformational Analysis of Six-Membered Cyclic Phenyl Phosphites
  作者：Barbara Gordillo、Catalina Garduno、Gerardo Guadarrama、Javier Hernandez

  DOI：10.1021/jo00121a041

  日期：1995.8

  A procedure for synthesizing potentially anancomeric equatorial phenyl phosphites (cis-l and eq-cis-2) is reported. Spectral characteristics and low-temperature NMR studies on the phenyl phosphites suggest that eq-cis-a is a system with a predominant chair conformation in solution. On the contrary, cis-l is conformationally heterogeneous.