(4S,5R)-2-(4-methoxyphenyl)-3,4-dimethyl-5-phenyl-1,3,2-oxaphospholane | 143236-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S,5R)-2-(4-methoxyphenyl)-3,4-dimethyl-5-phenyl-1,3,2-oxaphospholane
• 英文别名: (2R,4S,5R)-2-(4-methoxyphenyl)-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidine
• CAS: 143236-87-7
• 化学式: C₁₇H₂₀NO₂P
• 分子量: 301.325
• InChiKey: SAYWIASZRAIQMT-IBNJYYFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-2-(4-methoxyphenyl)-3,4-dimethyl-5-phenyl-1,3,2-oxaphospholane 、 2,3-丁二酮 以 正戊烷 为溶剂， 反应 24.0h， 以91%的产率得到(7R,8S)-2,3,8,9-tetramethyl-5-(4-methoxyphenyl)-7-phenyl-1,4,6-trioxa-9-aza-5-phospha(P^V)spiro<4.4>non-2-ene
  参考文献：
  名称：

  Pseudorotational, conformational, and NOE studies of pentacovalent spirophospholenes derived from ephedrine and .alpha.-diketones

  摘要：

  Variable-temperature NMR studies showed the chiral pentacovalent dioxaphospholenes 1-3 to be pseudorotationally stable below 60-degrees-C. DELTA-G(PSDRTN) for 1 and 2 were determined to be 22.0 +/- 2.1 kcal/mol and 33.0 +/- 2.6 kcal/mol, respectively. The DELTA-G(PSDRTN) for 2 is the largest value reported to date. H-1 NMR nuclear Overhauser effect studies on the major isomer of 1 confirmed that it was 1a and not 1b. Conformational analysis of the H-1 NMR data indicated a twist-envelope conformation for the ephedrine-derived five-membered ring.

  DOI：

  10.1021/jo00045a036
• 作为产物：
  描述：

  4-甲氧基苯基(二甲基氨基)氯化磷 在 三甲基氯硅烷 正丁基锂 、 1,10-菲罗啉 作用下， 以 乙二醇二甲醚 、 正庚烷 为溶剂， 反应 12.0h， 生成 (4S,5R)-2-(4-methoxyphenyl)-3,4-dimethyl-5-phenyl-1,3,2-oxaphospholane
  参考文献：
  名称：

  A flexible, highly efficient method for the preparation of homochiral oxazaphospholidine-boranes

  摘要：

  An efficient and operationally simple procedure for the synthesis of 2-substituted 3,4-dimethyl-5-phenyloxazaphospholidine derivatives has been developed. This new method permits the large scale preparation of a range of electronically and sterically differentiated homochiral monophosphine precursors.

  DOI：

  10.1016/s0040-4020(01)80637-2

文献信息

• A flexible, highly efficient method for the preparation of homochiral oxazaphospholidine-boranes
  作者：Susan Kult Sheehan、Meiqun Jiang、Lydia McKinstry、Tom Livinghouse、Donna Garton

  DOI：10.1016/s0040-4020(01)80637-2

  日期：1994.1

  An efficient and operationally simple procedure for the synthesis of 2-substituted 3,4-dimethyl-5-phenyloxazaphospholidine derivatives has been developed. This new method permits the large scale preparation of a range of electronically and sterically differentiated homochiral monophosphine precursors.
• Pseudorotational, conformational, and NOE studies of pentacovalent spirophospholenes derived from ephedrine and .alpha.-diketones
  作者：Cynthia K. McClure、Christopher W. Grote、Bruce A. Lockett

  DOI：10.1021/jo00045a036

  日期：1992.9

  Variable-temperature NMR studies showed the chiral pentacovalent dioxaphospholenes 1-3 to be pseudorotationally stable below 60-degrees-C. DELTA-G(PSDRTN) for 1 and 2 were determined to be 22.0 +/- 2.1 kcal/mol and 33.0 +/- 2.6 kcal/mol, respectively. The DELTA-G(PSDRTN) for 2 is the largest value reported to date. H-1 NMR nuclear Overhauser effect studies on the major isomer of 1 confirmed that it was 1a and not 1b. Conformational analysis of the H-1 NMR data indicated a twist-envelope conformation for the ephedrine-derived five-membered ring.