cis-1,6-dipyridyl-3-hexene | 169470-75-1

• 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: cis-1,6-dipyridyl-3-hexene
• CAS: 169470-75-1
• 化学式: C₁₆H₁₈N₂
• 分子量: 238.332
• InChiKey: BZQZXTUBCWAQNG-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cis-1,6-dipyridyl-3-hexene 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以78%的产率得到meso-1,6-bis(2-pyridyl)-hexane-3,4-diol
  参考文献：
  名称：

  A novel synthesis of optically active C2-symmetric pyridine derivatives. Efficient reaction of chiral triflates with 2-picolyllithium reagents

  摘要：

  A variety of optically active CZ-symmetric pyridine derivatives have been prepared from L- or D-tartaric acid as a chiral source via efficient coupling reactions of triflates with 2-picolyllithium reagents, and the utility of 17 and 18 as chiral ligands in the catalytic enantioselective addition of diethylzinc to benzaldehyde has been demonstrated (up to 41% ee). The synthetic procedure for the corresponding meso-isomer was also described.

  DOI：

  10.1016/0957-4166(95)00142-c
• 作为产物：
  描述：

  碳酸甲丙酯 、 [(Z)-4-甲基磺酰基氧基丁-2-烯基]甲烷磺酸酯 在 lithium diisopropyl amide 作用下， 生成 cis-1,6-dipyridyl-3-hexene
  参考文献：
  名称：

  A novel synthesis of optically active C2-symmetric pyridine derivatives. Efficient reaction of chiral triflates with 2-picolyllithium reagents

  摘要：

  A variety of optically active CZ-symmetric pyridine derivatives have been prepared from L- or D-tartaric acid as a chiral source via efficient coupling reactions of triflates with 2-picolyllithium reagents, and the utility of 17 and 18 as chiral ligands in the catalytic enantioselective addition of diethylzinc to benzaldehyde has been demonstrated (up to 41% ee). The synthetic procedure for the corresponding meso-isomer was also described.

  DOI：

  10.1016/0957-4166(95)00142-c

文献信息

• A novel synthesis of optically active C2-symmetric pyridine derivatives. Efficient reaction of chiral triflates with 2-picolyllithium reagents
  作者：Hiyoshizo Kotsuki、Yuichi Nakagawa、Narimasa Moriya、Hirotaka Tateishi、Masamitsu Ochi、Takayoshi Suzuki、Kiyoshi Isobe

  DOI：10.1016/0957-4166(95)00142-c

  日期：1995.5

  A variety of optically active CZ-symmetric pyridine derivatives have been prepared from L- or D-tartaric acid as a chiral source via efficient coupling reactions of triflates with 2-picolyllithium reagents, and the utility of 17 and 18 as chiral ligands in the catalytic enantioselective addition of diethylzinc to benzaldehyde has been demonstrated (up to 41% ee). The synthetic procedure for the corresponding meso-isomer was also described.