(3a'R,4S,7'R,7a'R)-7'-(6-bromopyridin-2-yl)-2,2,2',2'-tetramethyltetrahydrospiro[[1,3]dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'-ol | 532984-62-6

• 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: (3a'R,4S,7'R,7a'R)-7'-(6-bromopyridin-2-yl)-2,2,2',2'-tetramethyltetrahydrospiro[[1,3]dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'-ol
• CAS: 532984-62-6
• 化学式: C₁₇H₂₂BrNO₆
• 分子量: 416.269
• InChiKey: CYQDYVUBPSQPAH-ZLDMJSGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  79.27
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3a'R,4S,7'R,7a'R)-7'-(6-bromopyridin-2-yl)-2,2,2',2'-tetramethyltetrahydrospiro[[1,3]dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'-ol 在 三苯基膦 、 nickel dichloride 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到(3'aR,4S,7'R,7'aR)-7'-[6-[6-[(3'aR,4S,7'R,7'aR)-7'-hydroxy-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran]-7'-yl]pyridin-2-yl]pyridin-2-yl]-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran]-7'-ol
  参考文献：
  名称：

  Structural probing of d-fructose derived ligands for asymmetric addition of diethylzinc to aldehydes

  摘要：

  A series of new chiral ligands derived from D-fructose have been synthesized and applied in the enantioselective addition of diethylzinc to aldehydes. Comparison of the enantioselectivities obtained with these ligands demonstrated that the catalytic properties are highly dependent upon the structure of ligands, a rational explanation of the structural effects on the catalytic properties is provided. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00861-3
• 作为产物：
  描述：

  2,6-二溴吡啶 、 Shi's ketone 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 4.17h， 以45%的产率得到(3a'R,4S,7'R,7a'R)-7'-(6-bromopyridin-2-yl)-2,2,2',2'-tetramethyltetrahydrospiro[[1,3]dioxolane-4,6'-[1,3]dioxolo[4,5-c]pyran]-7'-ol
  参考文献：
  名称：

  Structural probing of d-fructose derived ligands for asymmetric addition of diethylzinc to aldehydes

  摘要：

  A series of new chiral ligands derived from D-fructose have been synthesized and applied in the enantioselective addition of diethylzinc to aldehydes. Comparison of the enantioselectivities obtained with these ligands demonstrated that the catalytic properties are highly dependent upon the structure of ligands, a rational explanation of the structural effects on the catalytic properties is provided. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00861-3