2-(2'-phenylselenoethyl)-perhydro-1,3-benzoxazine | 301311-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-(2'-phenylselenoethyl)-perhydro-1,3-benzoxazine
• 英文别名: (2S,4aS,7R,8aR)-4,4,7-trimethyl-2-(2-phenylselanylethyl)-2,3,4a,5,6,7,8,8a-octahydrobenzo[e][1,3]oxazine
• CAS: 301311-53-5
• 化学式: C₁₉H₂₉NOSe
• 分子量: 366.405
• InChiKey: XOPGRXWQIPSXAC-DDBAPUKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2'-phenylselenoethyl)-perhydro-1,3-benzoxazine 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以94%的产率得到N-(3'-phenylselenopropyl)-8-amino menthol
  参考文献：
  名称：

  Regio- and stereoselective 6- exo - trig radical cyclisations onto chiral perhydro-1,3-benzoxazines: synthesis of enantiopure 3-alkylpiperidines

  摘要：

  Enantiopure 3-alkyl substituted piperidines are prepared by diastereoselective 6-exo-trig cyclisation of perhydro-1,3-benzoxazines derived from (-)-(8)-amino menthol. The diastereoselective cyclisation is promoted by tributyltin hydride, and the competitive 1,5-hydrogen migration depends on the position of the acceptor double bond and the radical site. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00230-5
• 作为产物：
  描述：

  二苯基二硒醚 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 25.0h， 生成 2-(2'-phenylselenoethyl)-perhydro-1,3-benzoxazine
  参考文献：
  名称：

  Regio- and stereoselective 6- exo - trig radical cyclisations onto chiral perhydro-1,3-benzoxazines: synthesis of enantiopure 3-alkylpiperidines

  摘要：

  Enantiopure 3-alkyl substituted piperidines are prepared by diastereoselective 6-exo-trig cyclisation of perhydro-1,3-benzoxazines derived from (-)-(8)-amino menthol. The diastereoselective cyclisation is promoted by tributyltin hydride, and the competitive 1,5-hydrogen migration depends on the position of the acceptor double bond and the radical site. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00230-5

文献信息

• Synthesis of enantiopure 3-alkyl-perhydroazepines by diastereoselective 7-endo-radical cyclisation on a chiral 1,3-perhydrobenzoxazine derivative
  作者：Celia Andrés、Juan P. Duque-Soladana、Jesús M. Iglesias、Rafael Pedrosa

  DOI：10.1016/s0040-4039(99)00119-7

  日期：1999.3

  Competitive alkyl radical 6-exo/7-endo cyclisation on alpha,beta-unsaturated amides derived from chiral perhydrobenzoxazines are controlled by the alkene substitution pattern. Stereocontrol leading to 7-endo regioisomers is considerably higher and allows to prepare enantiopure hexahydroazepine derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Regio- and stereoselective 6- exo - trig radical cyclisations onto chiral perhydro-1,3-benzoxazines: synthesis of enantiopure 3-alkylpiperidines
  作者：Rafael Pedrosa、Celia Andrés、Juan P Duque-Soladana、Carlos D Rosón

  DOI：10.1016/s0957-4166(00)00230-5

  日期：2000.7

  Enantiopure 3-alkyl substituted piperidines are prepared by diastereoselective 6-exo-trig cyclisation of perhydro-1,3-benzoxazines derived from (-)-(8)-amino menthol. The diastereoselective cyclisation is promoted by tributyltin hydride, and the competitive 1,5-hydrogen migration depends on the position of the acceptor double bond and the radical site. (C) 2000 Elsevier Science Ltd. All rights reserved.