2-methyl-7-morpholino-1,2-dihydroisoquinolin-3(4H)-one | 877265-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-methyl-7-morpholino-1,2-dihydroisoquinolin-3(4H)-one
• 英文别名: 2-Methyl-7-morpholino-1,2-dihydroisoquinolin-3(4H)-one；2-methyl-7-morpholin-4-yl-1,4-dihydroisoquinolin-3-one
• CAS: 877265-13-9
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: SAMWNXYPLIZKIP-UHFFFAOYSA-N

物化性质

• 沸点：
  485.7±45.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-methyl-7-morpholino-1,2-dihydroisoquinolin-3(4H)-one 在 dimethyl sulfide borane 、 palladium diacetate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 反应 1.17h， 生成 4-(4-(benzothiophen-5-yl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl)morpholine maleate
  参考文献：
  名称：

  Initial Process Development and Scale-Up of the Synthesis of a Triple Reuptake Inhibitor ALB 109780

  摘要：

  Early process development toward a triple reuptake inhibitor is described. Three different routes were evaluated; one of them was optimized and scaled up to generate 470 g of API as this route minimized the formation of undesired side products. The selected route featured Eaton's reagent-mediated cyclization of a phenyl acetamide, copper-mediated Buchwald Hartwig coupling to install a morpholine moiety, and palladium-catalyzed alpha-arylation of a dihydroisoquinolinone to construct the core structure.

  DOI：

  10.1021/op3000064
• 作为产物：
  描述：

  2-(4-硝基苯基)乙酰氯 在 Eaton’s reagent 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 80.0 ℃ 、137.9 kPa 条件下， 反应 9.0h， 生成 2-methyl-7-morpholino-1,2-dihydroisoquinolin-3(4H)-one
  参考文献：
  名称：

  Initial Process Development and Scale-Up of the Synthesis of a Triple Reuptake Inhibitor ALB 109780

  摘要：

  Early process development toward a triple reuptake inhibitor is described. Three different routes were evaluated; one of them was optimized and scaled up to generate 470 g of API as this route minimized the formation of undesired side products. The selected route featured Eaton's reagent-mediated cyclization of a phenyl acetamide, copper-mediated Buchwald Hartwig coupling to install a morpholine moiety, and palladium-catalyzed alpha-arylation of a dihydroisoquinolinone to construct the core structure.

  DOI：

  10.1021/op3000064

文献信息

• Initial Process Development and Scale-Up of the Synthesis of a Triple Reuptake Inhibitor ALB 109780
  作者：Qiang Yang、Luckner G. Ulysse、Mark D. McLaws、Daniel K. Keefe、Brian P. Haney、Congxiang Zha、Peter R. Guzzo、Shuang Liu

  DOI：10.1021/op3000064

  日期：2012.3.16

  Early process development toward a triple reuptake inhibitor is described. Three different routes were evaluated; one of them was optimized and scaled up to generate 470 g of API as this route minimized the formation of undesired side products. The selected route featured Eaton's reagent-mediated cyclization of a phenyl acetamide, copper-mediated Buchwald Hartwig coupling to install a morpholine moiety, and palladium-catalyzed alpha-arylation of a dihydroisoquinolinone to construct the core structure.