3-cyano-1-<4-(1,3-dithian-2-yl)butyl>-1,4,5,6-tetrahydropyridine

• 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: 3-cyano-1-<4-(1,3-dithian-2-yl)butyl>-1,4,5,6-tetrahydropyridine
• 英文别名: 1-[4-(1,3-dithian-2-yl)butyl]-3,4-dihydro-2H-pyridine-5-carbonitrile
• 化学式: C₁₄H₂₂N₂S₂
• 分子量: 282.474
• InChiKey: QCLSZFJXZSGCHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氰基吡啶 在 sodium tetrahydroborate 、 potassium hydride 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 3-cyano-1-<4-(1,3-dithian-2-yl)butyl>-1,4,5,6-tetrahydropyridine
  参考文献：
  名称：

  α,β-Unsaturated Nitriles:  Stereoselective Conjugate Addition Reactions

  摘要：

  Dithiane anions undergo intramolecular conjugate additions with alpha,beta-unsaturated nitriles when a dithiane anion is tethered to N-1 of the 3-cyano-1,4,5,6-tetrahydropyridine nucleus. 3-Cyano-1-[2-(1,3-dithianyl-2-yl)ethyl]-1,4,5,6-tetrahydropyridine (1a) and the one-carbon homologue 1b cyclize in the presence of 12-crown-4 to generate indolizidine 3 and quinolizidine 9, in which the nitrile group exhibits a strong, thermodynamic preference for the axial orientation. Oxidation of Ib provides dithiane S-oxide 10 that undergoes a highly stereoselective conjugate addition to provide crystalline quinolizidine 13. The X-ray structure of 13 is reported and corroborates our ''peg-in-a-pocket'' principle for stereoselective conjugate additions with alpha,beta-unsaturated nitriles.

  DOI：

  10.1021/jo9619894

文献信息

• 3-Cyano-1-[4-(1,3-dithian-2-yl)butyl]-1,4,5,6-tetrahydropyridine
  作者：Z. Hussain、F. F. Fleming、R. E. Norman、S. C. Chang

  DOI：10.1107/s010827019501345x

  日期：1996.4.15

  The title nitrile 1-[4-(1,3-dithian-2-yl)butyl]-1,4,5,6-tetrahydropyridine-3-carbonitrile, C14H22N2S2} was prepared as part of our investigations into the conjugate addition reactions of unsaturated nitriles [Fleming & Pak (1995). J. Org. Chem. 60, 4299-4301]. The tetrahydropyridine ring adopts a half-chair conformation and is appended by a four-carbon chain to the dithiane ring which adopts a chair conformation.
• α,β-Unsaturated Nitriles:  Stereoselective Conjugate Addition Reactions
  作者：Fraser F. Fleming、Zahid Hussain、Douglas Weaver、Richard E. Norman

  DOI：10.1021/jo9619894

  日期：1997.3.1

  Dithiane anions undergo intramolecular conjugate additions with alpha,beta-unsaturated nitriles when a dithiane anion is tethered to N-1 of the 3-cyano-1,4,5,6-tetrahydropyridine nucleus. 3-Cyano-1-[2-(1,3-dithianyl-2-yl)ethyl]-1,4,5,6-tetrahydropyridine (1a) and the one-carbon homologue 1b cyclize in the presence of 12-crown-4 to generate indolizidine 3 and quinolizidine 9, in which the nitrile group exhibits a strong, thermodynamic preference for the axial orientation. Oxidation of Ib provides dithiane S-oxide 10 that undergoes a highly stereoselective conjugate addition to provide crystalline quinolizidine 13. The X-ray structure of 13 is reported and corroborates our ''peg-in-a-pocket'' principle for stereoselective conjugate additions with alpha,beta-unsaturated nitriles.