10-phenylsulfonylisobornyl 3-oxo-3-phenyl-2-triphenylphosphoranylidenepropanoate | 554450-42-9

• 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: 10-phenylsulfonylisobornyl 3-oxo-3-phenyl-2-triphenylphosphoranylidenepropanoate
• 英文别名: [(1S,2R,4R)-1-(benzenesulfonylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 3-oxo-3-phenyl-2-(triphenyl-λ5-phosphanylidene)propanoate
• CAS: 554450-42-9
• 化学式: C₄₃H₄₁O₅PS
• 分子量: 700.835
• InChiKey: FTCGLZKYLMOYDQ-MXUKBJHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  50.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  77.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  10-phenylsulfonylisobornyl 3-oxo-3-phenyl-2-triphenylphosphoranylidenepropanoate 在 N-溴代丁二酰亚胺(NBS) 、 叠氮基三甲基硅烷 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 10-phenylsulfonylisobornyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate
  参考文献：
  名称：

  Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates

  摘要：

  The dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral auxiliary, 10-phenylsulfonylisobornyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate, is reported. Its dehalogenation led to 10-phenylsulfonylisobomyl 2H-azirine-2-carboxylate as single stereoisomer together with the formation of 10-phenylsulfonylisobomyl acetate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00248-5
• 作为产物：
  描述：

  ((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid 在 吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 10-phenylsulfonylisobornyl 3-oxo-3-phenyl-2-triphenylphosphoranylidenepropanoate
  参考文献：
  名称：

  Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates

  摘要：

  The dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral auxiliary, 10-phenylsulfonylisobornyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate, is reported. Its dehalogenation led to 10-phenylsulfonylisobomyl 2H-azirine-2-carboxylate as single stereoisomer together with the formation of 10-phenylsulfonylisobomyl acetate. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00248-5