N-tert-Butyl-4-methoxy-6-methylisoindol-3-spiro-2'-(2',3'-dihydro-5'-hydroxynaphthalene)-1,1',4'-trione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-tert-Butyl-4-methoxy-6-methylisoindol-3-spiro-2'-(2',3'-dihydro-5'-hydroxynaphthalene)-1,1',4'-trione
• 英文别名: 2'-tert-butyl-8-hydroxy-4'-methoxy-6'-methylspiro[2H-naphthalene-3,3'-isoindole]-1,1',4-trione
• 化学式: C₂₃H₂₃NO₅
• 分子量: 393.439
• InChiKey: AXFYUKDCNNKZFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基-5-甲基苯甲酸 在 四(三苯基膦)钯 、 copper(I) bromide sodium hydroxide 、 氯化亚砜 、 三甲基氯化锡 、 叔丁基锂 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 35.5h， 生成 N-tert-Butyl-4-methoxy-6-methylisoindol-3-spiro-2'-(2',3'-dihydro-5'-hydroxynaphthalene)-1,1',4'-trione
  参考文献：
  名称：

  Synthesis of Antibiotics WS 5995 A and C and Related Compounds by Palladium-Catalyzed Coupling of 2-Bromonaphthoquinones with Organostannanes

  摘要：

  The synthesis of arylnaphthoquinones can be performed simply by using as the key reaction the Pd(0)- and Cu(I)-catalyzed coupling of arylstannanes with 2-bromonaphthoquinones as the electrophiles. The palladium-catalyzed coupling reaction is general and allows for the functionalization of the unprotected quinone nucleus with alkyl, alkenyl, and aryl substituents. The coupling process tolerates the presence of a chelated peri hydroxyl and steric crowding of a 2,6-disubstituted arylstannane, although the preparation of a 2,6,2',6'-tetrasubstituted biaryl by coupling of 2-bromo-3,5-bis(acetyloxy)-1,4-naphthoquinone as the electrophile with 2,6-disubstituted arylstannanes was unsuccessful. The syntheses of quinonoid antibiotics WS 5995 A and C was accomplished by using this method as the key step. Benz[b]phenanthridinone 1, hypothetical intermediate in the biosynthesis of benz[b]phenanthridine alkaloids, was also prepared from antibiotic WS 5995 C or by addition of ammonia to the 2-aryl-1,4-naphthoquinone 41 followed by heterocyclization.

  DOI：

  10.1021/jo00099a045

文献信息

• Synthesis of Antibiotics WS 5995 A and C and Related Compounds by Palladium-Catalyzed Coupling of 2-Bromonaphthoquinones with Organostannanes
  作者：Antonio M. Echavarren、Nuria Tamayo、Diego J. Cardenas

  DOI：10.1021/jo00099a045

  日期：1994.10

  The synthesis of arylnaphthoquinones can be performed simply by using as the key reaction the Pd(0)- and Cu(I)-catalyzed coupling of arylstannanes with 2-bromonaphthoquinones as the electrophiles. The palladium-catalyzed coupling reaction is general and allows for the functionalization of the unprotected quinone nucleus with alkyl, alkenyl, and aryl substituents. The coupling process tolerates the presence of a chelated peri hydroxyl and steric crowding of a 2,6-disubstituted arylstannane, although the preparation of a 2,6,2',6'-tetrasubstituted biaryl by coupling of 2-bromo-3,5-bis(acetyloxy)-1,4-naphthoquinone as the electrophile with 2,6-disubstituted arylstannanes was unsuccessful. The syntheses of quinonoid antibiotics WS 5995 A and C was accomplished by using this method as the key step. Benz[b]phenanthridinone 1, hypothetical intermediate in the biosynthesis of benz[b]phenanthridine alkaloids, was also prepared from antibiotic WS 5995 C or by addition of ammonia to the 2-aryl-1,4-naphthoquinone 41 followed by heterocyclization.