2-ethoxycarbonylmethyl-1,2-dihydro-1,4-dimethylquinoline | 151323-84-1

• 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: 2-ethoxycarbonylmethyl-1,2-dihydro-1,4-dimethylquinoline
• 英文别名: ethyl 2-(1,4-dimethyl-2H-quinolin-2-yl)acetate
• CAS: 151323-84-1
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: BUHWFLDFRMZMEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  348.6±35.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethoxycarbonylmethyl-1,2-dihydro-1,4-dimethylquinoline 在 air 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-2-ethoxycarbonylmethylidene-1,2-dihydro-1,4-dimethylquinoline
  参考文献：
  名称：

  Silicon-Assisted Ethoxycarbonylmethylation ofN-Methylquinolinium and Isoquinolinium Iodides

  摘要：

  A new regioselective route to 2-ethoxycarbonylmethyl- 1,2-dihydro-N-methylquinolines and 1-ethoxycarbonylmethyl-1,2-dihydro-N-methylisoquinolines is described starting from methylquinolinium or -isoquinolinium iodides and commercially available ethyltrimethylsilyl acetate (ETSA). The methylene carbanion was generated by fluorodesilylation using caesium fluoride. On exposure to air, the ethoxycarbonylmethyl adducts were oxidised, leading to the corresponding alkylidene derivatives 4 and 5, whereas 2a in solution led slowly to its regioisomer 6a.

  DOI：

  10.1002/1099-0690(200008)2000:16<2915::aid-ejoc2915>3.0.co;2-b
• 作为产物：
  描述：

  (三甲基硅基)乙酸乙酯 、 1,4-dimethylquinolinium iodide 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以71%的产率得到2-ethoxycarbonylmethyl-1,2-dihydro-1,4-dimethylquinoline
  参考文献：
  名称：

  Silicon-Assisted Ethoxycarbonylmethylation ofN-Methylquinolinium and Isoquinolinium Iodides

  摘要：

  A new regioselective route to 2-ethoxycarbonylmethyl- 1,2-dihydro-N-methylquinolines and 1-ethoxycarbonylmethyl-1,2-dihydro-N-methylisoquinolines is described starting from methylquinolinium or -isoquinolinium iodides and commercially available ethyltrimethylsilyl acetate (ETSA). The methylene carbanion was generated by fluorodesilylation using caesium fluoride. On exposure to air, the ethoxycarbonylmethyl adducts were oxidised, leading to the corresponding alkylidene derivatives 4 and 5, whereas 2a in solution led slowly to its regioisomer 6a.

  DOI：

  10.1002/1099-0690(200008)2000:16<2915::aid-ejoc2915>3.0.co;2-b

文献信息

• Fine Control of Regioselectivity in the Reduction of NAD⁺Analogues by Ketene Silyl Acetals
  作者：Shunichi Fukuzumi、Morifumi Fujita、Souta Noura、Junzo Otera

  DOI：10.1246/cl.1993.1025

  日期：1993.6

  Various NAD+ analogues are reduced regioselectively by ketene silyl acetals to afford the corresponding 2-, 6-, or 4-alkylated NADH analogues. The regioselectivity of the 1,2- (or 1,6-) vs. 1,4-reduction is finely controlled by the β-methyl-substitution of ketene silyl acetals, the position of methyl-substitution of NAD+ analogues, and the addition of Et4NCl or Bu4NF.

  各种 NAD+ 类似物通过乙缩酮硅烷进行区域选择性还原，从而得到相应的 2-、6- 或 4-烷基化 NADH 类似物。1,2-（或 1,6-）与 1,4-还原的区域选择性受烯甲硅基乙醛的 β-甲基取代、NAD+ 类似物的甲基取代位置以及 Et4NCl 或 Bu4NF 的添加等因素的严格控制。
• Silicon-Assisted Ethoxycarbonylmethylation ofN-Methylquinolinium and Isoquinolinium Iodides
  作者：Faïza Diaba、Cyril Le Houerou、Micheline Grignon-Dubois、Bernadette Rezzonico、Pierre Gerval

  DOI：10.1002/1099-0690(200008)2000:16<2915::aid-ejoc2915>3.0.co;2-b

  日期：2000.8

  A new regioselective route to 2-ethoxycarbonylmethyl- 1,2-dihydro-N-methylquinolines and 1-ethoxycarbonylmethyl-1,2-dihydro-N-methylisoquinolines is described starting from methylquinolinium or -isoquinolinium iodides and commercially available ethyltrimethylsilyl acetate (ETSA). The methylene carbanion was generated by fluorodesilylation using caesium fluoride. On exposure to air, the ethoxycarbonylmethyl adducts were oxidised, leading to the corresponding alkylidene derivatives 4 and 5, whereas 2a in solution led slowly to its regioisomer 6a.