cis-4-tert-butyl-1-phenylphosphorinane 1-oxide | 61332-81-8

• 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: cis-4-tert-butyl-1-phenylphosphorinane 1-oxide
• 英文别名: trans-4-tert-butyl-1-phenylphosphorinane 1-oxide；trans-4-t-butyl-1-phenylphosphorinane 1-oxide；4r-tert-butyl-1-phenyl-phosphinane 1c-oxide
• CAS: 61332-81-8；61332-82-9
• 化学式: C₁₅H₂₃OP
• 分子量: 250.321
• InChiKey: GJQJOUVXPNFRTE-XFHMXUHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  cis-4-tert-butyl-1-phenylphosphorinane 1-oxide 在 苯硅烷 作用下， 以 苯 为溶剂， 生成 1r-benzyl-4c-tert-butyl-1-phenyl-phosphinanium; bromide
  参考文献：
  名称：

  Preparation of cis- and trans-4-tert-butyl-1-phenylphosphorinane and a study of reaction stereochemistry of its derivatives

  摘要：

  DOI：

  10.1021/jo00428a008
• 作为产物：
  描述：

  四苯基二膦 在 sodium hydroxide 作用下， 反应 44.0h， 生成 cis-4-tert-butyl-1-phenylphosphorinane 1-oxide
  参考文献：
  名称：

  Preparation of cis- and trans-4-tert-butyl-1-phenylphosphorinane and a study of reaction stereochemistry of its derivatives

  摘要：

  DOI：

  10.1021/jo00428a008

文献信息

• Preparation, Reactions, and Stereochemistry of 4-tert-Butyl-1-chlorophosphorinane 1-Oxide and Derivatives
  作者：Maciej K. Tasz、Asher Gamliel、Oscar P. Rodriguez、Thomas M. Lane、Sheldon E. Cremer、Dennis W. Bennett

  DOI：10.1021/jo00125a012

  日期：1995.10

  The title compound 6 was synthesized as a model structure to study the stereochemical and mechanistic aspects of nucleophilic substitution at the phosphorus atom in a six-membered ring. Several synthetic methods were used to prepare 6, but in every case a mixture of diastereomers was obtained, in almost the same ratio. This mixture was used for the investigation of the reaction with several alcohols (methanol, ethanol, isopropyl alcohol) under acidic and/or basic conditions. Reactions with phenyllithium and two nitrogen nucleophiles, aniline and morpholine, were also carried out. The reactions led to mixtures of diastereomeric products; the ratio of these products did not always correspond to the diastereomeric ratio of starting material. Reactions of phosphinate esters were also studied, including kinetic measurements; the results strongly suggest an S(N)2 reaction mechanism. 4-tert-Butyl-1-fluorophosphorinane 1-oxide (mixture of isomers) was synthesized and its reactions with phenoxide ions and phenyllithium were studied; the overall stereochemical results of these transformations were similar to those of the title chlorides. The stereochemical assignments of the phenyl- (4), methoxy- (7), phenoxy- (10), and anilino (13) derivatives of 6 have been firmly anchored by X-ray studies; assignments for other compounds are tentative and based on spectroscopic measurements, including H-1, C-13, P-31, and O-17 NMR data.
• Cremer, Sheldon E.; Cowles, John M.; Gamliel, Asher, Phosphorus and Sulfur and the Related Elements, 1987, vol. 30, p. 369 - 372
  作者：Cremer, Sheldon E.、Cowles, John M.、Gamliel, Asher

  DOI：——

  日期：——
• Preparation of cis- and trans-4-tert-butyl-1-phenylphosphorinane and a study of reaction stereochemistry of its derivatives
  作者：Kenneth L. Marsi、James L. Jasperse、Francisco M. Llort、David B. Kanne

  DOI：10.1021/jo00428a008

  日期：1977.4