[2-(5-Hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-methoxymethoxy-5-methyl-phenyl]-carbamic acid tert-butyl ester | 137039-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [2-(5-Hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-methoxymethoxy-5-methyl-phenyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-(methoxymethoxy)-5-methylphenyl]carbamate
• CAS: 137039-32-8
• 化学式: C₂₄H₂₅NO₇
• 分子量: 439.465
• InChiKey: SRGOQBSCJAPQSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [2-(5-Hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-methoxymethoxy-5-methyl-phenyl]-carbamic acid tert-butyl ester 在 叔丁基过氧化氢 、 硫酸 、 苄基三甲基氢氧化铵 、 三氟乙酸酐 作用下， 反应 4.5h， 生成 Acetic acid 8-acetoxy-3-(2-acetoxy-6-acetylamino-4-methyl-phenyl)-1,4-dioxo-1,4-dihydro-naphthalen-2-yl ester
  参考文献：
  名称：

  Synthesis of benzo[b]carbazoloquinones by coupling of organostannanes with bromoquinones

  摘要：

  The synthesis of 5-carbonitrile-1,7-dihydroxy-3-methyl-5H-benzo[b]carbazole-6,11-dione, the quinone originally proposed as prekinamycin, was completed by using a palladium and copper catalyzed Stille reaction as the key step. A subsequent heterocyclization afforded a mixture of para(benzo[b]carbazole-6,11-dione) and ortho (benzo[a]carbazole-6,11-dione) quinones. A procedure for the N-cyanation of model indoles is also described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10085-0
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 四(三苯基膦)钯 、 copper(I) bromide sodium hydroxide 、 三甲基氯化锡 、 四丁基溴化铵 、 叔丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 [2-(5-Hydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-methoxymethoxy-5-methyl-phenyl]-carbamic acid tert-butyl ester
  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

• Palladium-catalyzed coupling of 2-bromonaphthoquinones with stannanes: a concise synthesis of antibiotics WS 5995 A and C and related compounds
  作者：Nuria Tamayo、Antonio M. Echavarren、M. Carmen Paredes

  DOI：10.1021/jo00023a004

  日期：1991.11

  The syntheses of antibiotics WS 5995 A and C and a hypothetical intermediate in the biosynthesis of the kinamycin antibiotics have been completed by using as the key step the palladium-catalyzed coupling of 2-bromo-1,4-naphthoquinones with stannanes.