5-methyl-3a,4,5,9b-tetrahydrofuro[3,4-c]quinolin-1(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-methyl-3a,4,5,9b-tetrahydrofuro[3,4-c]quinolin-1(3H)-one
• 英文别名: (3aS,9bR)-5-methyl-3,3a,4,9b-tetrahydrofuro[3,4-c]quinolin-1-one
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: LUTNJACBBPVLBW-GZMMTYOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3R,3aS,9bR)-5-methyl-3-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-3,3a,4,9b-tetrahydrofuro[3,4-c]quinolin-1-one 在 氢氧化钾 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以74%的产率得到5-methyl-3a,4,5,9b-tetrahydrofuro[3,4-c]quinolin-1(3H)-one
  参考文献：
  名称：

  Origin of Chiral Induction in Radical Reactions with the Diastereoisomers (5R)- and (5S)-5-l-Menthyloxyfuran-2[5H]-one

  摘要：

  Acetalization of 5-hydroxyfuran-2[5H]-one with l-menthol yields (5R)-(1) and (5S)-5-l-menthyloxyfuran-2[5H]-one (2) in equal amounts. The diastereomer 1 crystallizes preferentially. For the first time, the isolation of pure diastereoisomer 2 is reported. Different diastereoselectivities were observed in the radical tandem reaction of 1 and 2 with N,N-dimethylaniline. The privileged conformations in solution of the substrates and the products of the radical reaction were then determined, and X-ray crystal structure analyses were carried out on the reaction products. The different stereoselectivities in both cases are explained by different orientations of the menthyloxy substituent.

  DOI：

  10.1021/jo030292x

文献信息

• Visible-light-induced, Ir-catalyzed reactions of <i>N</i>-methyl-<i>N</i>-((trimethylsilyl)methyl)aniline with cyclic α,β-unsaturated carbonyl compounds
  作者：Dominik Lenhart、Thorsten Bach

  DOI：10.3762/bjoc.10.86

  日期：——

  reagent in visible-light-induced, iridium-catalyzed addition reactions to cyclic alpha,beta-unsaturated carbonyl compounds. Typical reaction conditions included the use of one equivalent of the reaction substrate, 1.5 equivalents of the aniline and 2.5 mol % (in MeOH) or 1.0 mol % (in CH2Cl2) [Ir(ppy)2(dtbbpy)]BF4 as the catalyst. Two major reaction products were obtained in combined yields of 30-67%. One

  N-甲基-N-((三甲基甲硅烷基) 甲基) 苯胺被用作试剂在可见光诱导，铱催化的环状α，β-不饱和羰基化合物的加成反应中。典型的反应条件包括使用一当量的反应底物、1.5 当量的苯胺和 2.5 mol%（在 MeOH 中）或 1.0 mol%（在 CH2Cl2 中）[Ir(ppy)2(dtbbpy)]BF4 作为催化剂。以30-67%的总产率获得两种主要反应产物。一种产物由氨甲基自由基加成产生，另一种产物是三环化合物，其很可能是由中间形成的α-羰基自由基在苯环上的攻击形成的。对于五元α、β-不饱和内酯和内酰胺底物，后一种产物是唯一分离的产物。
• Origin of Chiral Induction in Radical Reactions with the Diastereoisomers (5<i>R</i>)- and (5<i>S</i>)-5-<i>l</i>-Menthyloxyfuran-2[5<i>H</i>]-one
  作者：Siniša Marinković、Cédric Brulé、Norbert Hoffmann、Elise Prost、Jean-Marc Nuzillard、Véronique Bulach

  DOI：10.1021/jo030292x

  日期：2004.3.1

  Acetalization of 5-hydroxyfuran-2[5H]-one with l-menthol yields (5R)-(1) and (5S)-5-l-menthyloxyfuran-2[5H]-one (2) in equal amounts. The diastereomer 1 crystallizes preferentially. For the first time, the isolation of pure diastereoisomer 2 is reported. Different diastereoselectivities were observed in the radical tandem reaction of 1 and 2 with N,N-dimethylaniline. The privileged conformations in solution of the substrates and the products of the radical reaction were then determined, and X-ray crystal structure analyses were carried out on the reaction products. The different stereoselectivities in both cases are explained by different orientations of the menthyloxy substituent.