(Z)-1-Ethoxy-3-methoxy-1-<(trimethylsilyl)oxy>-1,3-butadiene

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-1-Ethoxy-3-methoxy-1-<(trimethylsilyl)oxy>-1,3-butadiene
• 英文别名: (Z)-1-ethoxy-3-methoxy-1-<(trimethylsilyl)oxy>buta-1,3-diene；(Z)-1-ethoxy-3-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene；[(1Z)-1-ethoxy-3-methoxybuta-1,3-dienoxy]-trimethylsilane
• 化学式: C₁₀H₂₀O₃Si
• 分子量: 216.352
• InChiKey: NTGAFMXWPQCQEF-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二溴对苯醌 、 (Z)-1-Ethoxy-3-methoxy-1-<(trimethylsilyl)oxy>-1,3-butadiene 以 苯 为溶剂， 反应 10.0h， 以45%的产率得到2-Bromo-8-hydroxy-6-methoxy-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

• Cycloaddition of Ketene Acetals with 4-Bromo-6-spiroepoxycyclohexa-2,4-dienone
  作者：Martine Mondon、Norbert Boeker、Jean-Pierre Gesson

  DOI：10.1039/a902751c

  日期：——

  4-Bromo-6-spiroepoxycyclohexa-2,4-dienone reacts as a diene in an inverse electron-demand reaction with 1-ethoxy-3-methoxy-1-trimethylsilyloxybuta-1,3-diene but as a dienophile with 1-ethoxy-3-methylene-4-(ethoxy trimethylsilyloxymethylene)-1-cyclohexene.

  4-Bromo-6-spiroepoxycyclohexa-2,4-dienone 在逆电子需求反应中作为二烯与 1-ethoxy-3-methoxy-1-trimethylsilyloxybuta-1,3-diene 反应，但作为亲二烯体与 1-ethoxy -3-亚甲基-4-(乙氧基三甲基甲硅烷基氧基亚甲基)-1-环己烯。
• 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.
• 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.