3-(N-methyl-N-(2'-bromobenzyl)carbamoyl)-2-chloropyridine

• 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-(N-methyl-N-(2'-bromobenzyl)carbamoyl)-2-chloropyridine
• 英文别名: N-[(2-bromophenyl)methyl]-2-chloro-N-methylpyridine-3-carboxamide
• 化学式: C₁₄H₁₂BrClN₂O
• mdl: MFCD13207009
• 分子量: 339.619
• InChiKey: DZHHHLHKDNHWCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(N-methyl-N-(2'-bromobenzyl)carbamoyl)-2-chloropyridine 在 dibromobis(triphenylphosphine)nickel(II) 、 四乙基碘化铵 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以42%的产率得到6,7-dihydro-6-methyl-5-oxopyridino<3,2-d>-2-benzazepin
  参考文献：
  名称：

  NAD(P+/NAD(P)H Models. 83. Molecular Asymmetry with a Carbonyl Group: Electronically Controlled Stereochemistry in the Reaction of NAD(P)+/NAD(P)H Analogs

  摘要：

  The N-methylpyridinium salt of 6,7,dihydro-6-methyl-5-oxopyridino[3,2-d]-2-benzazepin has been synthesized. The salt has axial chirality with respect to the orientation of the carbonyl dipole. An enantiomer of the cation has been obtained as the iodide salt. Reduction of the salt results in the corresponding dihydropyridine derivative stereospecifically. The stereochemistry of the reduction is controlled entirely by the electronic effect of the carbonyl dipole.

  DOI：

  10.1021/ja00097a021
• 作为产物：
  描述：

  2-氯烟酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-(N-methyl-N-(2'-bromobenzyl)carbamoyl)-2-chloropyridine
  参考文献：
  名称：

  NAD(P+/NAD(P)H Models. 83. Molecular Asymmetry with a Carbonyl Group: Electronically Controlled Stereochemistry in the Reaction of NAD(P)+/NAD(P)H Analogs

  摘要：

  The N-methylpyridinium salt of 6,7,dihydro-6-methyl-5-oxopyridino[3,2-d]-2-benzazepin has been synthesized. The salt has axial chirality with respect to the orientation of the carbonyl dipole. An enantiomer of the cation has been obtained as the iodide salt. Reduction of the salt results in the corresponding dihydropyridine derivative stereospecifically. The stereochemistry of the reduction is controlled entirely by the electronic effect of the carbonyl dipole.

  DOI：

  10.1021/ja00097a021

文献信息

• NAD(P+/NAD(P)H Models. 83. Molecular Asymmetry with a Carbonyl Group: Electronically Controlled Stereochemistry in the Reaction of NAD(P)+/NAD(P)H Analogs
  作者：Atsuyoshi Ohno、Akihiro Tsutsumi、Yasushi Kawai、Norimasa Yamazaki、Yuji Mikata、Mutsuo Okamura

  DOI：10.1021/ja00097a021

  日期：1994.9

  The N-methylpyridinium salt of 6,7,dihydro-6-methyl-5-oxopyridino[3,2-d]-2-benzazepin has been synthesized. The salt has axial chirality with respect to the orientation of the carbonyl dipole. An enantiomer of the cation has been obtained as the iodide salt. Reduction of the salt results in the corresponding dihydropyridine derivative stereospecifically. The stereochemistry of the reduction is controlled entirely by the electronic effect of the carbonyl dipole.