(S)-diethyl 3-oxo-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyridazine-1,2(3H)-dicarboxylate | 1334472-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (S)-diethyl 3-oxo-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyridazine-1,2(3H)-dicarboxylate
• 英文别名: diethyl (7aS)-3-oxo-5,6,7,7a-tetrahydrocyclopenta[c]pyridazine-1,2-dicarboxylate
• CAS: 1334472-48-8
• 化学式: C₁₃H₁₈N₂O₅
• 分子量: 282.296
• InChiKey: DQLZEVWMIYTQCU-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  环戊基乙酰氯 、 偶氮二甲酸二乙酯 在 TMS-quinidine hydrochloride 、 三乙胺 作用下， 以 甲苯 为溶剂， 以92%的产率得到(S)-diethyl 3-oxo-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyridazine-1,2(3H)-dicarboxylate
  参考文献：
  名称：

  Highly Enantioselective γ-Amination of α,β-Unsaturated Acyl Chlorides with Azodicarboxylates: Efficient Synthesis of Chiral γ-Amino Acid Derivatives

  摘要：

  The cinchona alkaloid-catalyzed gamma-amination of alpha,beta-unsaturated acyl chlorides with azodicarboxylates to give the corresponding dihydropyridazinones in good yields with high enantioselectivities has been developed. Reductive ring opening of the dihydropyridazinones afforded series of cyclic and acyclic gamma-amino acid derivatives in good yields with high enantiopurity.

  DOI：

  10.1021/ja206819y

文献信息

• Highly Enantioselective γ-Amination of α,β-Unsaturated Acyl Chlorides with Azodicarboxylates: Efficient Synthesis of Chiral γ-Amino Acid Derivatives
  作者：Li-Tao Shen、Li-Hui Sun、Song Ye

  DOI：10.1021/ja206819y

  日期：2011.10.12

  The cinchona alkaloid-catalyzed gamma-amination of alpha,beta-unsaturated acyl chlorides with azodicarboxylates to give the corresponding dihydropyridazinones in good yields with high enantioselectivities has been developed. Reductive ring opening of the dihydropyridazinones afforded series of cyclic and acyclic gamma-amino acid derivatives in good yields with high enantiopurity.