Methyl 2-(1,4-dihydro-5-hydroxy-3-methoxy-1,4-dioxo-2-naphthalenyl)-3-methoxy-5-methylbenzoate | 76959-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Methyl 2-(1,4-dihydro-5-hydroxy-3-methoxy-1,4-dioxo-2-naphthalenyl)-3-methoxy-5-methylbenzoate
• 英文别名: methyl 2-(3-methoxy-5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzoate；methyl 2-(5-hydroxy-3-methoxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoate
• CAS: 76959-18-7
• 化学式: C₂₁H₁₈O₇
• 分子量: 382.37
• InChiKey: YNCOFTPHHLBCNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 2-(1,4-dihydro-5-hydroxy-3-methoxy-1,4-dioxo-2-naphthalenyl)-3-methoxy-5-methylbenzoate 在 ammonium hydroxide 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 51.0h， 生成 Methyl 2-(3-acetamido-5-hydroxy-1,4-dioxonaphthalen-2-yl)-3-methoxy-5-methylbenzoate
  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：

  trimethoxonium tetrafluoroborate 、 Antibiotic WS-5995 C 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以76%的产率得到Methyl 2-(1,4-dihydro-5-hydroxy-3-methoxy-1,4-dioxo-2-naphthalenyl)-3-methoxy-5-methylbenzoate
  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

• Structure and Synthesis of New Anticoccidial Antibiotics Isolated from Streptomyces Auranticolor
  作者：Hiroichi Ikushima、Shigehiro Takase、Yoshio Kawai、Yoshikuni Itoh、Masanori Okamoto、Hirokazu Tanaka

  DOI：10.1080/00021369.1983.10865932

  日期：1983.10

  The structures of two new anticoccidial antibiotics, WS-5995A and B, produced by Streptomyces auranticolor, were determined as I and II, respectively, on the basis of spectral and chemical evidence.WS-5995A (I), having 5H-benzo[d]naphtho[2,3-b]pyran as its mother skeleton, was synthesized by coupling the diazonium salt prepared from the anthranilic acid (IX) to 3-hydroxy juglone (VIII).

  WS-5995A（I）以5H-苯并[d]萘并[2,3-b]吡喃为母体骨架，是通过将蚁酸（IX）与3-羟基丁二酮（VIII）偶联制备的重氮盐合成的。
• 1,4-Naphtoquinone derivatives and their use in treating coccidiosis
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04414226A1

  公开（公告）日：1983-11-08

  1,4-naphthoquinone derivatives represented by the following general formula: ##STR1## (wherein R.sup.1 represents a hydrogen atom, a hydroxy group, a lower alkoxy group or an arylthio group, R.sup.2 represents a carboxy group, an esterified carboxy group or an amidated carboxy group or, when taken together, R.sup.1 and R.sup.2 form a group of ##STR2## R.sup.3 represents a hydrogen atom or a lower alkyl group, R.sup.4 represents a lower alkyl group, R.sup.5 represents a hydrogen atom or a halogen atom, and R.sup.6 represents a hydrogen atom, a lower alkyl group or a lower alkanoyl group), and the salts of the carboxy group thereof, which are novel compounds having an anticoccidium activity, and which can be obtained by synthesis or, partly, by cultivation of Streptomyces auranticolor.

  1,4-萘醌衍生物由以下一般式代表：##STR1##（其中R.sup.1代表氢原子、羟基、较低的烷氧基或芳基硫基，R.sup.2代表羧基、酯化羧基或酰胺化羧基或者，当一起时，R.sup.1和R.sup.2形成##STR2##的基团，R.sup.3代表氢原子或较低的烷基基团，R.sup.4代表较低的烷基基团，R.sup.5代表氢原子或卤素原子，R.sup.6代表氢原子、较低的烷基基团或较低的烷酰基团），以及其羧基的盐，这些是具有抗球虫活性的新化合物，可以通过合成或部分通过栽培金黄链霉菌（Streptomyces auranticolor）获得。
• 1,4-Napthoquinone derivatives and use thereof
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04530845A1

  公开（公告）日：1985-07-23

  1,4-naphthoquinone derivatives represented by the following general formula: ##STR1## (wherein R.sup.1 represents a hydrogen atom, a hydroxy group, a lower alkoxy group or an arylthio group, R.sup.2 represents a carboxy group, an esterified carboxy group or an amidated carboxy group or, when taken together, R.sup.1 and R.sup.2 form a group of ##STR2## R.sup.3 represents a hydrogen atom or a lower alkyl group, R.sup.4 represents a lower alkyl group, R.sup.5 represents a hydrogen atom or a halogen atom, and R.sup.6 represents a hydrogen atom, a lower alkyl group or a lower alkanoyl group), and the salts of the carboxy group thereof, which are novel compounds having an anticoccidium activity, and which can be obtained by synthesis or, partly, by cultivation of Streptomyces auranticolor.

  以下是由下列通用式表示的1,4-萘醌衍生物：##STR1##（其中R.sup.1代表氢原子，羟基，较低的烷氧基或芳基硫基，R.sup.2代表羧基，酯化羧基或酰胺化羧基或当它们一起取时，R.sup.1和R.sup.2形成一个##STR2##的基团，R.sup.3代表氢原子或较低的烷基，R.sup.4代表较低的烷基，R.sup.5代表氢原子或卤素原子，R.sup.6代表氢原子，较低的烷基或较低的脂肪酰基），以及其羧基盐，这些化合物是具有抗球虫活性的新化合物，可以通过合成或部分通过Streptomyces auranticolor的培养获得。
• 1,4-NAPHTHOQUINONE DERIVATIVES AND USE THEREOF
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0047323A1

  公开（公告）日：1982-03-17

  1,4-naphthoquinone derivates represented by the following general formula: wherein R1 represents a hydrogen atom, a hydroxy group, a lower alkoxy group or an arylthio group, R2 represents a carboxy group, an esterified carboxy group or an amidated carboxy qroup or, when taken toqether, R1 and R2 form a group of represents a hydrogen atom or a lower alkyl group, R4 represents a lower alkyl group, R5 represents a hydrogen atom or a halogen atom, and R6 represents a hydrogen atom, a lower alkyl group or a lower alkanoyl group), and the salts of the carboxy group thereof, which are novel compounds having an anti-coccidium activity, and which can be obtained by synthesis or, partly, by cultivation of Streptomyces auranticolor.

  由以下通式代表的 1，4-萘醌衍生物： 其中 R1 代表氢原子、羟基、低级烷氧基或芳硫基； R2 代表羧基、酯化羧基或酰胺化羧基；或当 R1 和 R2 形成一个基团时，R1 代表氢原子或低级烷基； R4 代表低级烷基； R5 代表氢原子或卤原子。 代表氢原子或低级烷基，R4 代表低级烷基，R5 代表氢原子或卤原子，R6 代表氢原子、低级烷基或低级烷酰基）及其羧基的盐，它们是具有抗球虫活性的新型化合物，可通过合成或部分通过培养 Auranticolor 链霉菌获得。
• 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.