10-phenylsulfonylisobornyl 3-phenyl-2H-azirine-2-carboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 10-phenylsulfonylisobornyl 3-phenyl-2H-azirine-2-carboxylate
• 英文别名: [(1S,2R,4R)-1-(benzenesulfonylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2S)-3-phenyl-2H-azirine-2-carboxylate
• 化学式: C₂₅H₂₇NO₄S
• 分子量: 437.56
• InChiKey: OHBXFCLOSPNMSB-VQPBKUBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  D(+)-10-樟脑磺酸 在 吡啶 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 叠氮基三甲基硅烷 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 38.08h， 生成 10-phenylsulfonylisobornyl 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

文献信息

• Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
  作者：Teresa M.V.D Pinho e Melo、Ana L Cardoso、António M.d'A Rocha Gonsalves

  DOI：10.1016/s0040-4020(03)00248-5

  日期：2003.3

  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.