(3R,8aS)-(-)-6-ethyl-3-phenyl-3,7,8,8a-tetrahydro-2H-oxazolo<3,2-a>pyridine | 185383-99-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (3R,8aS)-(-)-6-ethyl-3-phenyl-3,7,8,8a-tetrahydro-2H-oxazolo<3,2-a>pyridine
• 英文别名: (3R,5R,8R,8aS)-5-isopropyl-8-methyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine；(3R,8aS)-6-ethyl-3-phenyl-3,7,8,8a-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridine
• CAS: 185383-99-7
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: SAIQPTGUXYMHJF-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (3R,8aS)-(-)-6-ethyl-3-phenyl-3,7,8,8a-tetrahydro-2H-oxazolo<3,2-a>pyridine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 盐酸 、 乙醚 、 乙醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (5S,8S,8aR)-(+)-8-ethyl-5-propyl-octahydroindolizidine hydrochloride
  参考文献：
  名称：

  A short enantioselective access to 2,3,6-trialkylpiperidines and 5,8-dialkylindolizidines

  摘要：

  An enantioselective access to 2,3,6-trialkylpiperidines 5 is described. This sequence is illustrated by the four-step syntheses, from salts 1, of piperidine 6 and indolizidines 7 and 8. The overall yields are in the range 10-15%. The stereochemistry of intermediates is discussed, supported by two X-ray studies, and comparison with analogs. Stereochemical properties of intermediate oxazolidine derivatives 4 were used to orient the syntheses towards different diastereoisomers such as 7 or 8. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00566-3
• 作为产物：
  描述：

  3-乙基吡啶 在 aluminum oxide 、 sodium dithionite 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 、 正戊烷 为溶剂， 反应 1.0h， 生成 (3R,8aS)-(-)-6-ethyl-3-phenyl-3,7,8,8a-tetrahydro-2H-oxazolo<3,2-a>pyridine
  参考文献：
  名称：

  Pyridine-Derived Oxazolidines as Chiral 3-Alkyl-4,5-dihydropyridinium and 3-Alkyl-3,4,5,6-tetrahydropyridinium Salt Equivalents

  摘要：

  DOI：

  10.1021/jo961323+

文献信息

• 1,4-dihydropyridines from dithionite reduction of pyridinium salts without electron-withdrawing groups as substituents
  作者：Yung-Sing Wong、Christian Marazano、Dino Gnecco、Bhupesh C. Das

  DOI：10.1016/s0040-4039(00)75796-0

  日期：1994.1

  Conditions have been established for the sodium dithionite (Na2S2O4) reduction of pyridinium salts 1 lacking electron-withdrawing substituents to their corresponding 1,4-dihydropyridines (1,4-DHPs) 2, a reaction which was previously reported to fail. The importance of hydrophobic effects for this reduction to take place could be recognized from the results obtained. The present procedure offers a very

  已经建立了亚硫酸钠（Na 2 S 2 O 4）还原没有吸电子取代基的吡啶鎓盐1到其相应的1,4-二氢吡啶（1,4-DHPs）2的条件，该反应先前被报道为失败。从获得的结果可以认识到疏水作用对于这种减少发生的重要性。本方法提供了通往许多1，4-DHP 2，特别是一系列手性衍生物如5和9的非常方便的途径。
• Pyridine-Derived Oxazolidines as Chiral 3-Alkyl-4,5-dihydropyridinium and 3-Alkyl-3,4,5,6-tetrahydropyridinium Salt Equivalents
  作者：Yung-Sing Wong、Christian Marazano、Dino Gnecco、Yves Génisson、Angèle Chiaroni、Bhupesh C. Das

  DOI：10.1021/jo961323+

  日期：1997.2.1
• A short enantioselective access to 2,3,6-trialkylpiperidines and 5,8-dialkylindolizidines
  作者：Yung-Sing Wong、Dino Gnecco、Christian Marazano、Angèle Chiaroni、Claude Riche、Annick Billion、Bhupesh C. Das

  DOI：10.1016/s0040-4020(98)00566-3

  日期：1998.8

  An enantioselective access to 2,3,6-trialkylpiperidines 5 is described. This sequence is illustrated by the four-step syntheses, from salts 1, of piperidine 6 and indolizidines 7 and 8. The overall yields are in the range 10-15%. The stereochemistry of intermediates is discussed, supported by two X-ray studies, and comparison with analogs. Stereochemical properties of intermediate oxazolidine derivatives 4 were used to orient the syntheses towards different diastereoisomers such as 7 or 8. (C) 1998 Elsevier Science Ltd. All rights reserved.