(1S)-10-(phenylsulfonyl)isobornyl (triphenylphosphoranylidene)acetate | 554450-39-4

• 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: (1S)-10-(phenylsulfonyl)isobornyl (triphenylphosphoranylidene)acetate
• 英文别名: 10-phenylsulfonylisobornyl triphenylphosphoranylideneacetate；[(1S,2R,4R)-1-(benzenesulfonylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-(triphenyl-lambda5-phosphanylidene)acetate；[(1S,2R,4R)-1-(benzenesulfonylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] 2-(triphenyl-λ5-phosphanylidene)acetate
• CAS: 554450-39-4
• 化学式: C₃₆H₃₇O₄PS
• 分子量: 596.727
• InChiKey: PIXGIKVYOPXVRF-ULZAEUJESA-N

物化性质

• 熔点：
  201-202 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  733.5±56.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-10-(phenylsulfonyl)isobornyl (triphenylphosphoranylidene)acetate 在 N-溴代丁二酰亚胺(NBS) 、 叠氮基三甲基硅烷 、 三乙胺 作用下， 以 四氢呋喃 、 正庚烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.08h， 生成 10-phenylsulfonylisobornyl 3-phenylquinoxaline-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 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 (1S)-10-(phenylsulfonyl)isobornyl (triphenylphosphoranylidene)acetate
  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

• Novel Asymmetric Wittig Reaction: Synthesis of Chiral Allenic Esters
  作者：Teresa M. V. D. Pinho e Melo、Ana L. Cardoso、António M. d’A. Rocha Gonsalves、João Costa Pessoa、José A. Paixão、Ana M. Beja

  DOI：10.1002/ejoc.200400413

  日期：2004.12

  Wittig reactions between 10-(phenylsulfonyl)isobornyl (triphenylphosphoranylidene)acetates (1 and 6) and ketenes resulted in asymmetric induction, with the selective synthesis of allenes with axial chirality. Use of the (1R)-(−)-10-(phenylsulfonyl)isoborneol unit allows the synthesis of allenes with S configuration, whereas use of the (1S)-(+)-10-(phenylsulfonyl)isoborneol unit produces allenes with

  10-（苯磺酰基）异冰片基（三苯基亚膦基）乙酸酯（1 和 6）和烯酮之间的 Wittig 反应导致不对称诱导，选择性合成具有轴手性的丙二烯。使用 (1R)-(-)-10-(苯基磺酰基)异冰片醇单元允许合成具有 S 构型的丙二烯，而使用 (1S)-(+)-10-(苯基磺酰基)异冰片醇单元生成具有 R 构型的丙二烯配置。(1R)-(-)-10-(苯基磺酰基)异冰片基(S)-5,5-二甲基六-2,3-二烯酸酯(2e)的结构通过X射线晶体学确定。进行了丙二酸酯的手性光学研究，证实获得了两组对映体衍生物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Contribution to the synthesis of chiral allenic esters
  作者：Teresa M.V.D. Pinho e Melo、Ana L. Cardoso、António M.d'A. Rocha Gonsalves、Richard C. Storr、João Costa Pessoa、José A. Paixão、Ana M. Beja、Manuela Ramos Silva

  DOI：10.1016/s0040-4039(03)01585-5

  日期：2003.8

  phosphorus ylide bearing a 10-phenylsulfonylisoborneol unit reacted with ketenes, generated in situ from acid chlorides and triethylamine, to give allenic compounds. The reaction with methylketene led to asymmetric induction with the selective synthesis of an allene with axial chirality corresponding to an S configuration. The structure of the chiral allene 10-phenylsulfonylisobornyl penta-2,3-dienoate

  带有10-苯基磺酰基异冰片醇单元的磷内鎓盐与烯酮反应，后者是从酰氯和三乙胺就地生成的，从而得到烯丙基化合物。与甲基烯酮的反应导致不对称诱导，并选择性合成了具有与S构型相对应的轴向手性的丙二烯。通过X射线晶体学测定手性烯丙基10-苯基磺酰基异冰片基戊基2，3-二烯酸酯的结构。进行了手性烯丙基衍生物的手性研究。