(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 | 256429-71-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (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
• CAS: 256429-71-7
• 化学式: C₂₂H₃₁NO₃
• 分子量: 357.493
• InChiKey: MZIIOOZXJZDDAA-FDEREBHBSA-N

物化性质

• 熔点：
  116 °C
• 沸点：
  497.0±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (5R)-(L-menthyloxy)-2(5H)-furanone 、 N,N-二甲基苯胺 在 丙酮 、 米氏酮 作用下， 以 乙腈 为溶剂， 以74%的产率得到(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
  参考文献：
  名称：

  Stereoselective radical-tandem reaction of aniline derivatives with (5R)-5-menthyloxy-2,5-dihydrofuran-2-one initiated by photochemical induced electron transfer

  摘要：

  苯胺的简单烷基衍生物与手性呋喃酮的自由基串联反应可以高产率立体选择性地进行；呋喃酮还作为氧化剂参与了重芳烃化过程（形成副产品），在该过程中，它可以被丙酮有效取代。

  DOI：

  10.1039/a906051k

文献信息

• Diastereoselective Radical Tandem Addition-Cyclization Reactions of Aromatic Tertiary Amines by Semiconductor-Sensitized Photochemical Electron Transfer
  作者：Siniša Marinković、Norbert Hoffmann

  DOI：10.1002/ejoc.200400102

  日期：2004.7

  The diastereoselective radical tandem addition-cyclization reaction of N,N-dimethylaniline (2) with menthyloxyfuranone 1 was initiated by photochemically induced electron transfer using inorganic semiconductors (TiO2, ZnS, SiC and SnO2) as sensitizers. The rearomatization step, which also causes the partial reduction of 1, was studied by isotopic labeling experiments using deuterated derivatives of

  N,N-二甲基苯胺 (2) 与薄荷氧基呋喃酮 1 的非对映选择性自由基串联加成环化反应是通过使用无机半导体（TiO2、ZnS、SiC 和 SnO2）作为敏化剂的光化学诱导电子转移引发的。重构化步骤也导致 1 的部分还原，通过同位素标记实验研究了使用 2 的氘代衍生物。半导体表面对这些过程的影响已被表征，并与在均质条件下获得的结果进行比较。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Diastereoselective Tandem Addition−Cyclization Reactions of Unsaturated Tertiary Amines Initiated by Photochemical Electron Transfer (PET)
  作者：Samuel Bertrand、Norbert Hoffmann、Stéphane Humbel、Jean Pierre Pete

  DOI：10.1021/jo001166l

  日期：2000.12.1

  Polycyclic molecules and tetrahydroquinoleines were obtained in a tandem reaction involving the diastereoselective addition of or-aminoalkyl radicals to (5R)-5-menthyloxy-2[5H]-furanone 1. The facial diastereoselectivity on 1 is greater than or equal to 90%. The alpha -aminoalkyl radicals were produced from tertiary amines by photachemical-induced electron transfer. When N,N-dialkylanilines 19 were used as starting tertiary amines, a rearomatization step was involved and important side reactions of 1 were observed. A mechanistic study involving isotopic labeling of the starting amine indicated that the byproducts resulted from reduction of 1 during the rearomatization process. An efficient optimization of the reaction was obtained by simply adding acetone or cyclopentanone as mild oxidants to the reaction mixture. The side products resulting from reduction of the furanone 1 were completely suppressed under these conditions, and the yields of the tettahydroquinolines 21a-i, 22a-f, and 26g-i were doubled.
• 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.
• Stereoselective radical-tandem reaction of aniline derivatives with (5R)-5-menthyloxy-2,5-dihydrofuran-2-one initiated by photochemical induced electron transfer
  作者：Samuel Bertrand、Norbert Hoffmann、Jean-Pierre Pete、Véronique Bulach

  DOI：10.1039/a906051k

  日期：——

  The radical tandem reaction of simple alkyl derivatives of aniline to a chiral furanone can be carried out stereoselectively in high yields; the furanone is also involved as oxidant in a rearomatisation process (formation of byproducts) where it can be replaced efficiently by acetone.

  苯胺的简单烷基衍生物与手性呋喃酮的自由基串联反应可以高产率立体选择性地进行；呋喃酮还作为氧化剂参与了重芳烃化过程（形成副产品），在该过程中，它可以被丙酮有效取代。