8-methyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline-4-carboxylic acid ethyl ester | 746662-85-1

• 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: 8-methyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 8-methyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline-4-carboxylate
• CAS: 746662-85-1
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: VWOJPGQNNJPYQM-UHFFFAOYSA-N

物化性质

• 沸点：
  384.1±42.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-methyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline-4-carboxylic acid ethyl ester 在 硫酸 、 copper dichloride 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以85%的产率得到7-methyl-3,4-dihydro-1H-pyrano[3,4-b]quinolin-1-one
  参考文献：
  名称：

  甘氨酸衍生物喹啉融合内酯和内酰胺的催化方法

  摘要：

  探索了一种双催化剂体系[氯化铜（II）硫酸，（CuCl 2 -H 2 SO 4）]-促进甘氨酸衍生物与2,3-二氢呋喃或2,3-二氢吡咯的好氧氧化反应，得到了有效合成高价值的喹啉融合内酯和内酰胺。以简洁的三步顺序完成了这种新方法在合成荧光素A的生物活性C环延伸类似物方面的应用。

  DOI：

  10.1002/adsc.201500513
• 作为产物：
  描述：

  2,3-二氢呋喃 、 ethyl 2-(4-methylphenylimino)acetate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以62%的产率得到8-methyl-2,3,3a,4,5,9b-hexahydro-furo[3,2-c]quinoline-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Iron Catalyzed Dual-Oxidative Dehydrogenative (DOD) Tandem Annulation of Glycine Derivatives with Tetrahydrofurans

  摘要：

  A novel iron-catalyzed dual-oxidative dehydrogenative (DOD) tandem annulation of glycine derivatives with tetrahydrofurans (THFs) for the synthesis of high value quinoline fused lactones has been developed. The reactions were performed under mild reaction conditions. And the use of cheap substrates (glycine derivatives and THF) and an even cheaper simple inorganic iron salt as the catalyst makes this protocol very attractive for potential synthetic applications.

  DOI：

  10.1021/acs.orglett.5b02504

文献信息

• BORRIONE, ELISABETTA;PRATO, MAURIZIO;SCORRANO, GIANFRANCO;STIVANELLO, MAR+, J. HETEROCYCL. CHEM., 25,(1988) N, C. 1831-1835
  作者：BORRIONE, ELISABETTA、PRATO, MAURIZIO、SCORRANO, GIANFRANCO、STIVANELLO, MAR+

  DOI：——

  日期：——
• Iron Catalyzed Dual-Oxidative Dehydrogenative (DOD) Tandem Annulation of Glycine Derivatives with Tetrahydrofurans
  作者：Congde Huo、Fengjuan Chen、Yong Yuan、Haisheng Xie、Yajun Wang

  DOI：10.1021/acs.orglett.5b02504

  日期：2015.10.16

  A novel iron-catalyzed dual-oxidative dehydrogenative (DOD) tandem annulation of glycine derivatives with tetrahydrofurans (THFs) for the synthesis of high value quinoline fused lactones has been developed. The reactions were performed under mild reaction conditions. And the use of cheap substrates (glycine derivatives and THF) and an even cheaper simple inorganic iron salt as the catalyst makes this protocol very attractive for potential synthetic applications.
• A Catalytic Approach to Quinoline Fused Lactones and Lactams from Glycine Derivatives
  作者：Congde Huo、Yong Yuan、Fengjuan Chen、Yajun Wang

  DOI：10.1002/adsc.201500513

  日期：2015.11.16

  A dual catalyst system [copper(II) chloride-sulfuric acid, (CuCl2-H2SO4)]-promoted aerobic oxidative reaction of glycine derivatives with 2,3-dihydrofurans or 2,3-dihydropyrroles has been explored, affording an efficient synthesis of high value quinoline fused lactones and lactams. The application of this new methodology to the synthesis of a bioactive C ring extension analogue of luotonin A has been

  探索了一种双催化剂体系[氯化铜（II）硫酸，（CuCl 2 -H 2 SO 4）]-促进甘氨酸衍生物与2,3-二氢呋喃或2,3-二氢吡咯的好氧氧化反应，得到了有效合成高价值的喹啉融合内酯和内酰胺。以简洁的三步顺序完成了这种新方法在合成荧光素A的生物活性C环延伸类似物方面的应用。