trimethyl (5SR,6SR)-1,3-dichloro-8-(N,N-diethylamino)-5,6-dihydro-5-hydroxy-5,6,7-isoquinolinetricarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trimethyl (5SR,6SR)-1,3-dichloro-8-(N,N-diethylamino)-5,6-dihydro-5-hydroxy-5,6,7-isoquinolinetricarboxylate
• 英文别名: trimethyl (5SR,6SR)-1,3-dichloro-8-diethylamino-5,6-dihydro-5-hydroxyisoquinoline-5,6,7-tricarboxylate；trimethyl (5S,6S)-1,3-dichloro-8-(diethylamino)-5-hydroxy-6H-isoquinoline-5,6,7-tricarboxylate
• 化学式: C₁₉H₂₂Cl₂N₂O₇
• 分子量: 461.299
• InChiKey: QQENMGUATDQZLE-BFUOFWGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  富马酸二甲酯 、 甲基4,6-二氯-3-(二乙基氨基)呋喃并[3,4-c]吡啶-1-羧酸酯 以 苯 为溶剂， 生成 trimethyl (5SR,6SR)-1,3-dichloro-8-(N,N-diethylamino)-5,6-dihydro-5-hydroxy-5,6,7-isoquinolinetricarboxylate
  参考文献：
  名称：

  Trimethyl (5SR,6SR)-1,3-dichloro-8-diethylamino-5,6-dihydro-5-hydroxyisoquinoline-5,6,7-tricarboxylate

  摘要：

  The title compound, C19H22Cl2N2O7, has four independent molecules in the asymmetric unit with no pseudosymmetry. In each of the four molecules the fused cyclohexadiene ring adopts a skew-boat conformation, with two of the three methoxycarbonyl groups in the axial orientation and the third methoxycarbonyl and the diethylamino groups attached equatorially. The hydroxyl groups are involved in O-H ... O intermolecular hydrogen bonds with carbonyl-O atoms to form infinite chains in the [2 (1) over bar 0] direction.

  DOI：

  10.1107/s010827019900311x

文献信息

• Synthesis and Reactions of a Stable <i>o</i>-Quinoid 10-π-Electron System, Furo[3,4-<i>c</i>]pyridine
  作者：Tarun K. Sarkar、Sunil K. Ghosh、Tahsin J. Chow

  DOI：10.1021/jo991886w

  日期：2000.5.1

  4-c]pyridine-1-carboxylate (6), an intermediate in the Hamaguchi-Ibata reaction involving the Rh(II)-catalyzed intramolecular reaction of a diazo group with the carbonyl of an adjacent amido group, has been isolated and characterized. PM3 calculations reveal the heat of formation (DeltaH(f)) of this remarkably stable molecule to be -77.7 kcal/mol. Compound 6 undergoes a facile Diels-Alder cycloaddition with a variety

  4,6-二氯-3-（二乙基氨基）呋喃[3,4-c]吡啶-1-甲酸甲酯（6），是Rama（II）催化的重氮分子内分子反应的reaction口-伊巴达反应中间体具有相邻酰胺基的羰基的基团已经被分离和表征。PM3的计算表明，这种非常稳定的分子的形成热（DeltaH（f））为-77.7 kcal / MOl。化合物6与各种亲二烯体进行容易的Diels-Alder环加成反应，从而通过最初形成的环加合物的开环得到多取代的异喹啉衍生物。在每种情况下，环加成都以高区域选择性进行，其中吸电子基团位于氨基的邻位。最有利的FMO相互作用是在氮杂异苯并呋喃6的HOMO和亲双烯体的LUMO之间。