(3,4-dihydroisoquinolin-2(1H)-yl)(2-hydroxynaphthalen-1-yl)methanone | 1602982-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3,4-dihydroisoquinolin-2(1H)-yl)(2-hydroxynaphthalen-1-yl)methanone
• CAS: 1602982-04-6
• 化学式: C₂₀H₁₇NO₂
• 分子量: 303.36
• InChiKey: RFNJVEYHNZJYDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3,4-dihydroisoquinolin-2(1H)-yl)(2-hydroxynaphthalen-1-yl)methanone 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 1-azido-3,3-dimethyl-3-(1H)-1,2-benziodoxole 、 (4R,4'R)-2,2'-(4,6-二苯并呋喃二基)双[4,5-二氢-4-苯基恶唑] 作用下， 以 二氯甲烷 为溶剂， 反应 9.5h， 以91%的产率得到(S)-1-azido-1-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)naphthalen-2(1H)-one
  参考文献：
  名称：

  Enantioselective Copper-Catalyzed Electrophilic Dearomative Azidation of β-Naphthols

  摘要：

  The first example of copper-catalyzed enantioselective dearomative azidation of beta-naphthols using a readily available N-3-transfer reagent is reported. A series of 2-hydroxy-1-naphthamides bearing a complex N-substituent were converted to the corresponding products in high yields with up to 96% ee, and chiral 1-azido-2-hydroxy-1-naphthoates were obtained with up to 90% ee under mild reaction conditions. The azides could be further transformed into the corresponding 1,2,3-triazoles smoothly via "click" reaction.

  DOI：

  10.1021/acs.orglett.9b02604
• 作为产物：
  描述：

  2-羟基-1-萘甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 (3,4-dihydroisoquinolin-2(1H)-yl)(2-hydroxynaphthalen-1-yl)methanone
  参考文献：
  名称：

  Enantioselective Copper-Catalyzed Electrophilic Dearomative Azidation of β-Naphthols

  摘要：

  The first example of copper-catalyzed enantioselective dearomative azidation of beta-naphthols using a readily available N-3-transfer reagent is reported. A series of 2-hydroxy-1-naphthamides bearing a complex N-substituent were converted to the corresponding products in high yields with up to 96% ee, and chiral 1-azido-2-hydroxy-1-naphthoates were obtained with up to 90% ee under mild reaction conditions. The azides could be further transformed into the corresponding 1,2,3-triazoles smoothly via "click" reaction.

  DOI：

  10.1021/acs.orglett.9b02604

文献信息

• Predictably Selective (sp³)C–O Bond Formation through Copper Catalyzed Dehydrogenative Coupling: Facile Synthesis of Dihydro-oxazinone Derivatives
  作者：Atanu Modak、Uttam Dutta、Rajesh Kancherla、Soham Maity、Mohitosh Bhadra、Shaikh M. Mobin、Debabrata Maiti

  DOI：10.1021/ol500670h

  日期：2014.5.16

  An intramolecular dehydrogenative (sp3)C–O bond formation in salicylamides can be initiated by an active Cu/O2 species to generate pharamaceutically relevant dihydro-oxazinones. Experimental findings suggest that stereoelectronic parameters in both coupling partners are controlling factors for site selectivity in bond formation. Mechanistic investigations including isotope labeling, kinetic studies

  水杨酰胺中分子内脱氢（sp 3）C–O键的形成可以由活性Cu / O 2物种引发，以生成药物相关的二氢-恶嗪酮。实验结果表明，两个偶合伙伴中的立体电子参数是键形成中位点选择性的控制因素。包括同位素标记在内的机械研究，动力学研究有助于提出催化循环。该方法为正在研究的新药CX-614的合成提供了便利，该新药具有寻找帕金森氏病和阿尔茨海默氏病治疗的潜力。