(3S,5S,7aR)-3,5-diphenylhexahydropyrrolo<2,1-b><1,3>oxazole | 205442-90-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S,5S,7aR)-3,5-diphenylhexahydropyrrolo<2,1-b><1,3>oxazole
• 英文别名: [3S,5S,7aR]-3,5-diphenyl-hexahydropyrrolo[2,1-b]oxazole；(3S,5S,7aR)-3,5-diphenyl-2,3,5,6,7,7a-hexahydropyrrolo[2,1-b][1,3]oxazole
• CAS: 205442-90-6
• 化学式: C₁₈H₁₉NO
• 分子量: 265.355
• InChiKey: CJUMCBUDTXYCOC-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯基氯化镁 、 (3S,5S,7aR)-3,5-diphenylhexahydropyrrolo<2,1-b><1,3>oxazole 在 氯化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2S)-2-(2R,5R)-2,5-diphenyltetrahydro-1H-1-pyrrolyl-2-phenylethan-1-ol 、 (2S)-2-(2R,5S)-2,5-diphenyltetrahydro-1H-1-pyrrolyl-2-phenylethan-1-ol
  参考文献：
  名称：

  Short Enantioselective Syntheses of trans-5-Alkylprolines from New Functionalized Amino Alcohols

  摘要：

  GraphicsAmino alcohols, having an enol ether function, cyclized in acidic medium to give quantitatively diastereosomerically pure bicyclic compounds that were transformed in five steps in enantiopure trans-5-alkylproline derivatives.

  DOI：

  10.1021/jo8014243
• 作为产物：
  描述：

  (2S)-2-((1S)-4-methoxy-1-phenylbut-3-enylamino)-2-phenylethanol 在 硫酸 、 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 以100%的产率得到(3S,5S,7aR)-3,5-diphenylhexahydropyrrolo<2,1-b><1,3>oxazole
  参考文献：
  名称：

  Short Enantioselective Syntheses of trans-5-Alkylprolines from New Functionalized Amino Alcohols

  摘要：

  GraphicsAmino alcohols, having an enol ether function, cyclized in acidic medium to give quantitatively diastereosomerically pure bicyclic compounds that were transformed in five steps in enantiopure trans-5-alkylproline derivatives.

  DOI：

  10.1021/jo8014243

文献信息

• Asymmetric Syntheses of 2-Substituted and 2,5-Disubstituted Pyrrolidines from (3<i>S</i>,5<i>R</i>,7a<i>R</i>)-5-(Benzotriazol-1-yl)-3-phenyl[2,1-<i>b</i>]oxazolopyrrolidine
  作者：Alan R. Katritzky、Xi-Lin Cui、Baozhen Yang、Peter J. Steel

  DOI：10.1021/jo9821426

  日期：1999.3.1

  1-b]oxazolopyrrolidine (6), whose crystal structure was confirmed by X-ray crystallography. Novel chiral pyrrolidine synthon 6 reacts with organosilicon (allyltrimethylsilanes and vinyloxytrimethylsilanes), organophosphorus, organozinc, and Grignard reagents to afford chiral 2-substituted and 2,5-disubstituted pyrrolidines.

  在一个步骤中，苯并三唑，2,5-二甲氧基四氢呋喃和（S）-苯基甘氨醇给出80％的（3S，5R，7aR）-5-（苯并三唑-1-基）-3-苯基-[2,1-b]恶唑烷吡咯烷（6），其晶体结构通过X射线晶体学证实。新型手性吡咯烷合成子6与有机硅（烯丙基三甲基硅烷和乙烯基氧基三甲基硅烷），有机磷，有机锌和格氏试剂反应，得到手性的2-取代的和2,5-二取代的吡咯烷。
• A short asymmetric synthesis of 2,5-disubstituted pyrrolidines
  作者：Alan R. Katritzky、Xi-Lin Cui、Baozhen Yang、Peter J. Steel

  DOI：10.1016/s0040-4039(98)00134-8

  日期：1998.3

  A novel approach to chiral 2,5-disubstituted pyrrolidines, starting from chiral 2-phenyl-glycinol, 1,5-dimethoxytetrahydrofuran, and benzotriazole, involves the diastereoselective substitution by Grignard reagents of a benzotriazolyl group in a crystalline intermediate obtained in high yield.

  从手性2-苯基-甘醇，1,5-二甲氧基四氢呋喃和苯并三唑开始的手性2,5-二取代的吡咯烷的新方法涉及在高产率获得的结晶中间体中用格氏试剂非对映选择性取代苯并三唑基。
• Palladium-Catalyzed Cyclization of Unsaturated β-Amino Alcohols: A New Access to Enantiopure Bicyclic Oxazolidines
  作者：Jeanne Alladoum、Emmanuel Vrancken、Pierre Mangeney、Sylvain Roland、Catherine Kadouri-Puchot

  DOI：10.1021/ol901375w

  日期：2009.8.20

  Chiral unsaturated beta-amino alcohols possessing a dialkylamino function cyclize in the presence of Pd(II) catalysts and reoxidants to afford enantiopure bicyclic oxazolidines with total regio- and stereocontrol. The scope and limitations of this transformation have been studied.
• Short Enantioselective Syntheses of <i>trans</i>-5-Alkylprolines from New Functionalized Amino Alcohols
  作者：Jeanne Alladoum、Sylvain Roland、Emmanuel Vrancken、Pierre Mangeney、Catherine Kadouri-Puchot

  DOI：10.1021/jo8014243

  日期：2008.12.19

  GraphicsAmino alcohols, having an enol ether function, cyclized in acidic medium to give quantitatively diastereosomerically pure bicyclic compounds that were transformed in five steps in enantiopure trans-5-alkylproline derivatives.