5-Hydroxy-2-<6-methoxy-4-methyl-2-<(diethylamino)carbonyl>phenyl>-1,4-naphthoquinone | 161621-04-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Hydroxy-2-<6-methoxy-4-methyl-2-<(diethylamino)carbonyl>phenyl>-1,4-naphthoquinone
• 英文别名: N,N-diethyl-2-(5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzamide
• CAS: 161621-04-1
• 化学式: C₂₃H₂₃NO₅
• 分子量: 393.439
• InChiKey: BSECHHRYERJOLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-2-<6-methoxy-4-methyl-2-<(diethylamino)carbonyl>phenyl>-1,4-naphthoquinone 在 盐酸 、 sodium acetate 、 氯化铵 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 28.0h， 生成 8-Hydroxy-1-methoxy-3-methylbenzophenanthridine-5,7,12-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
• 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 56.5h， 生成 5-Hydroxy-2-<6-methoxy-4-methyl-2-<(diethylamino)carbonyl>phenyl>-1,4-naphthoquinone
  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 <i>O</i> ‐linked Cyclitol Analogues of Gilvocarcin M and Antibacterial Activity
  作者：Ehesan U. Sharif、Pei Shi、George A. O'Doherty

  DOI：10.1002/ijch.202100015

  日期：2021.7

  development of the Gilvocarcins, a class of bioactive C-aryl glycoside natural products. More specifically, the origins behind the proposed O- to C-glycoside migration in the evolution of the biosynthesis for these classes of Angucycline antibiotic natural products. For stability reasons a 5a-carbasugar motif was used to mimic the sugar portion of the molecule and of synthetic ease the proposed abiotic rearrangement

  提出了两种非天然区域异构糖基化 Gilvocarcin 类似物作为模型化合物，以研究 Gilvocarcins（一类具有生物活性的C-芳基糖苷天然产物）生物合成发展背后的起源。更具体地说，在这些类Angucycline 抗生素天然产物的生物合成进化过程中，所提议的O - 到C - 糖苷迁移背后的起源。出于稳定性原因，使用 5a-carbasugar 基序来模拟分子的糖部分，并且为了合成容易，提议的非生物重排移动糖类似物及其O-糖苷键。两种提议的区域异构类似物是通过区域发散合成途径合成的，并具有类似光信的反向环化反应以安装碳糖基序。两种区域异构的 Gilvocarcin 类似物被评估为抗生素，Gilvocarcin M 作为对照。与 Gilvocarcin M 相比，两种异构体中只有一种显示出弱的抗生素活性。
• De Frutos, Oscar; Atienza, Carmen; Echavarren, Antonio M., European Journal of Organic Chemistry, 2001, # 1, p. 163 - 171
  作者：De Frutos, Oscar、Atienza, Carmen、Echavarren, Antonio M.

  DOI：——

  日期：——
• Syntheses of fenanthroviridone, gilvocarcin BE-12406X2, and antibiotic ws 5995b based on the palladium and copper catalyzed coupling of organostannanes with bromoquinones
  作者：Óscar de Frutos、Antonio M. Echavarren

  DOI：10.1016/s0040-4039(96)02056-4

  日期：1996.12

  A total synthesis of fenanthroviridone, gilvocarcin BE-12406X(2) antibiotic WS 5995B is described based on the palladium and copper catalyzed coupling reaction of sterically hindered aryl stannanes with a 2-bromonaphthoquinone. Copyright (C) 1996 Elsevier Science Ltd
• 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.