(4S)-4-甲基-2,2,2-三苯基-1,3,2lambda5-二氧杂磷杂环戊烷 | 104762-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4S)-4-甲基-2,2,2-三苯基-1,3,2lambda5-二氧杂磷杂环戊烷
• 英文名称: (S)-4-methyl-2,2,2-triphenyl-1,2,2λ⁵-dioxaphospholane
• 英文别名: (S)-4-methyl-2,2,2-triphenyl-1,3,2γ⁵-dioxaphospholane；4-Methyl-2,2,2-triphenyl-1,3,2λ⁵-dioxaphospholane；(S)-4-Methyl-2,2,2-triphenyl-1,3,2l⁵-dioxaphospholane；(S)-4-Methyl-2,2,2-triphenyl-2lambda*5*-[1,3,2]dioxaphospholane；(4S)-4-methyl-2,2,2-triphenyl-1,3,2λ5-dioxaphospholane
• CAS: 104762-38-1；141553-95-9；141553-96-0；141610-02-8
• 化学式: C₂₁H₂₁O₂P
• 分子量: 336.37
• InChiKey: CYLNOCGJEVHIHT-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S)-4-甲基-2,2,2-三苯基-1,3,2lambda5-二氧杂磷杂环戊烷 在 sodium azide 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以93%的产率得到2-Azido-1-propanol
  参考文献：
  名称：

  The regioselective and stereospecific substitution of unsymmetrical 1,2-diols using the 1,3,2λ5-dioxaphospholane methodology.

  摘要：

  Stereospecific tosylate (-OTs) or azide (N3-) substitution at the C-4 stereocenter of a monosubstituted 1,3,2-lambda-5-dioxaphospholane (the equivalent of the C-2 stereocenter in an unsymmetrical 1,2-diol) is readily achieved by treatment with either p-toluenesulfonic acid (p-TsOH) in tetrahydrofuran solvent or p-TsOH/sodium azide in acetonitrile solvent, respectively.

  DOI：

  10.1016/s0040-4020(01)96904-2
• 作为产物：
  描述：

  bromotriphenylphosphonium bromide 在 sodium ethanolate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 (4S)-4-甲基-2,2,2-三苯基-1,3,2lambda5-二氧杂磷杂环戊烷
  参考文献：
  名称：

  A New and Improved Preparation of Acyclic .sigma.-Dialkoxyphosphoranes

  摘要：

  DOI：

  10.1021/jo00087a047

文献信息

• Highly regioselective and stereospecific functionalization of 1,2-propanediol with trimethyl(X)silanes employing the 1,3,2.lambda.5-dioxaphospholane methodology
  作者：Isabel Mathieu-Pelta、Slayton A. Evans

  DOI：10.1021/jo00038a032

  日期：1992.6

  The regioselective ring opening of (S)-4-methyl-2,2,2-triphenyl-1,3,2-lambda-5-dioxaphospholane (2) [prepared from the bis(transoxyphosphoranylation) of (S)-1,2-propanediol (1) with diethoxytriphenylphosphorane (DTPP)] was initiated with several trimethylsilyl reagents (Me3SiX: X = PhS, I, Br, Cl, CN, and N3) to afford the regioisomeric (silyloxy)phosphonium salts. A stereospecific extrusion of triphenylphosphine oxide from these oxyphosphonium salts gave predominantly the thermodynamically less stable C-2-X-substituted derivatives with nearly complete inversion of stereochemistry at the C-2 stereogenic center (i.e., X = PhS).
• Mathieu-Pelta, Isabel; Evans, Slayton A., Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 77, # 1-4, p. 219
  作者：Mathieu-Pelta, Isabel、Evans, Slayton A.

  DOI：——

  日期：——
• Mathieu-Pelta Isabel, Evans Slayton A., J. Org. Chem, 59 (1994) N 8, S 2234-2237
  作者：Mathieu-Pelta Isabel, Evans Slayton A.

  DOI：——

  日期：——
• A New and Improved Preparation of Acyclic .sigma.-Dialkoxyphosphoranes
  作者：Isabel Mathieu-Pelta、Slayton A. Evans

  DOI：10.1021/jo00087a047

  日期：1994.4
• The regioselective and stereospecific substitution of unsymmetrical 1,2-diols using the 1,3,2λ5-dioxaphospholane methodology.
  作者：Anne Pautard-Cooper、Slayton A. Evans、William Rand Kenan

  DOI：10.1016/s0040-4020(01)96904-2

  日期：1991.1

  Stereospecific tosylate (-OTs) or azide (N3-) substitution at the C-4 stereocenter of a monosubstituted 1,3,2-lambda-5-dioxaphospholane (the equivalent of the C-2 stereocenter in an unsymmetrical 1,2-diol) is readily achieved by treatment with either p-toluenesulfonic acid (p-TsOH) in tetrahydrofuran solvent or p-TsOH/sodium azide in acetonitrile solvent, respectively.