(2R,2'R)-1-(1',2',3',6'-tetrahydropyridin-2'-yl)pent-4-en-2-ol | 756821-41-7

• 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: (2R,2'R)-1-(1',2',3',6'-tetrahydropyridin-2'-yl)pent-4-en-2-ol
• 英文别名: (2R)-1-[(2R)-1,2,3,6-tetrahydropyridin-2-yl]pent-4-en-2-ol
• CAS: 756821-41-7
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: JKUBRVHQKGXHJN-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,2'R)-1-(1',2',3',6'-tetrahydropyridin-2'-yl)pent-4-en-2-ol 在 platinum(IV) oxide 氢气 作用下， 以 various solvent(s) 为溶剂， 反应 8.0h， 以94%的产率得到(-)-halosaline
  参考文献：
  名称：

  Concise asymmetric synthesis of (−)-halosaline and (2R,9aR)-(+)-2-hydroxy-quinolizidine by ruthenium-catalyzed ring-rearrangement metathesis

  摘要：

  A ruthenium-catalyzed ring opening-ring closing metathesis reaction serves as the key step in the stereoselective synthesis of a new enantiopure 2-substituted-4.5-dehydropiperidine skeleton, a valuable intermediate for the synthesis of piperidine alkaloids (such as halosaline) and of hydroxylated quinolizidines (such as (2R,9aR)-(+)-2-hydroxy-quinolizidine). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.051
• 作为产物：
  描述：

  (1R,6R)-acetic acid 6-(N-p-toluenesulfonylamino)cyclohept-3-enyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) sodium hydroxide 、 萘 、 sodium 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.67h， 生成 (2R,2'R)-1-(1',2',3',6'-tetrahydropyridin-2'-yl)pent-4-en-2-ol
  参考文献：
  名称：

  Concise asymmetric synthesis of (−)-halosaline and (2R,9aR)-(+)-2-hydroxy-quinolizidine by ruthenium-catalyzed ring-rearrangement metathesis

  摘要：

  A ruthenium-catalyzed ring opening-ring closing metathesis reaction serves as the key step in the stereoselective synthesis of a new enantiopure 2-substituted-4.5-dehydropiperidine skeleton, a valuable intermediate for the synthesis of piperidine alkaloids (such as halosaline) and of hydroxylated quinolizidines (such as (2R,9aR)-(+)-2-hydroxy-quinolizidine). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.051

文献信息

• Concise asymmetric synthesis of (−)-halosaline and (2R,9aR)-(+)-2-hydroxy-quinolizidine by ruthenium-catalyzed ring-rearrangement metathesis
  作者：Giordano Lesma、Sergio Crippa、Bruno Danieli、Daniele Passarella、Alessandro Sacchetti、Alessandra Silvani、Andrea Virdis

  DOI：10.1016/j.tet.2004.06.051

  日期：2004.7

  A ruthenium-catalyzed ring opening-ring closing metathesis reaction serves as the key step in the stereoselective synthesis of a new enantiopure 2-substituted-4.5-dehydropiperidine skeleton, a valuable intermediate for the synthesis of piperidine alkaloids (such as halosaline) and of hydroxylated quinolizidines (such as (2R,9aR)-(+)-2-hydroxy-quinolizidine). (C) 2004 Elsevier Ltd. All rights reserved.