(E)-3-tert-butyldimethylsiloxy-1-(3,4,5-trimethoxyphenyl)-1,3-butadiene | 196957-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3-tert-butyldimethylsiloxy-1-(3,4,5-trimethoxyphenyl)-1,3-butadiene
• 英文别名: tert-butyl-dimethyl-[(3E)-4-(3,4,5-trimethoxyphenyl)buta-1,3-dien-2-yl]oxysilane
• CAS: 196957-42-3
• 化学式: C₁₉H₃₀O₄Si
• 分子量: 350.53
• InChiKey: OKJMMJJZMWQFCV-ZHACJKMWSA-N

物化性质

• 沸点：
  407.2±45.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-tert-butyldimethylsiloxy-1-(3,4,5-trimethoxyphenyl)-1,3-butadiene 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 9.0h， 生成 2-phenyl-9-methoxy-4-(3,4,5-trimethoxyphenyl)-6H-pyrrolo[3,4-c]carbazole-1,3-dione
  参考文献：
  名称：

  Open Analogues of Arcyriaflavin A. Synthesis through Diels−Alder Reaction between Maleimides and 1-Aryl-3-tert-butyldimethylsiloxy-1,3-butadienes

  摘要：

  The preparation of a range of open analogues of arcyriaflavin A is described. The synthetic approach is based on the use of perhydroisoindole-1,3,5-triones as key intermediates, which were obtained via Diels-Alder methodology using 1-aryl-3-siloxy-1,3-butadienes as starting materials. Fischer indolization and aromatization processes afforded different methoxy-substituted arylpyrrolocarbazoles. The stereochemistry and conformation of the Diels-Alder products and the regiochemistry of the indolization reactions are supported by NMR and molecular modeling studies.

  DOI：

  10.1021/jo991815x
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 1.75h， 生成 (E)-3-tert-butyldimethylsiloxy-1-(3,4,5-trimethoxyphenyl)-1,3-butadiene
  参考文献：
  名称：

  （±）-7-（3,4,5-三甲氧基苯基）-7-脱氧柔红霉素的合成。蒽环类似物的新家族

  摘要：

  描述了7-芳基蒽环类似物的第一代表性化合物的合成。用Diels-Alder环加成法将由容易获得的材料制得的1-烷基-3-三烷基甲硅烷氧基二烯转化为四环酮，然后将其转化为（±）-7-（3,4,5-三甲氧基苯基）-7-脱氧柔红霉素。研究了目标化合物和中间产物的构象。

  DOI：

  10.1016/s0040-4020(98)00304-4

文献信息

• Synthesis of (±)-7-(3,4,5-trimethoxyphenyl)-7-deoxyidarubicinone. A new family of anthracycline analogues
  作者：Esther Caballero、Manuel Medarde、Rafael Pelaez-Lamamie de Clairac、Heidi Sahagún、Fernando Tomé

  DOI：10.1016/s0040-4020(98)00304-4

  日期：1998.5

  The synthesis of the first representative compound of 7-aryl anthracycline analogues, is described. 1-Alkyl-3-trialkylsiloxydienes, prepared from readily available materials, are transformed through a Diels-Alder cycloaddition into a tetracyclic ketone, that is converted into (±)-7-(3,4,5-trimethoxyphenyl)-7-deoxyidarubicinone. The conformations of the target compound and intermediate products are

  描述了7-芳基蒽环类似物的第一代表性化合物的合成。用Diels-Alder环加成法将由容易获得的材料制得的1-烷基-3-三烷基甲硅烷氧基二烯转化为四环酮，然后将其转化为（±）-7-（3,4,5-三甲氧基苯基）-7-脱氧柔红霉素。研究了目标化合物和中间产物的构象。
• Reactivity of 4-tert-Butyldimethylsiloxy-1,2,3,6-tetrahydropyridines with Hydrazines
  作者：Javier Figueroa、Esther Caballero、Pilar Puebla、Fernando Tomé、Manuel Medarde

  DOI：10.3390/11110929

  日期：——

  The reactivity of 6-(nitrophenyl or trimethoxyphenyl)-4-tert-butyldimethyl- siloxy-1,2,3,6-tetrahydropyridine derivatives with hydrazines under acid conditions is described. The structure of the products isolated − hydrazones, pyrazolines or pyridazinones − depended on the conditions used. In addition, a systematic study of the reaction outcomes was carried out by introducing variations on the substituents of the tetrahydropyridine ring.

  介绍了 6-（硝基苯基或三甲氧基苯基）-4-叔丁基二甲基硅氧基-1,2,3,6-四氢吡啶衍生物在酸性条件下与肼的反应性。分离出的产物（肼、吡唑或哒嗪酮）的结构取决于所使用的条件。此外，通过对四氢吡啶环上的取代基进行变化，对反应结果进行了系统研究。
• Diels-alder reactivity of 1-alkoxyphenyl-3-trialkylsiloxy-1,3-dienes
  作者：Marta Adeva、Esther Caballero、Francine García、Manuel Medarde、Heidi Sahagún、Fernando Tomé

  DOI：10.1016/s0040-4039(97)01588-8

  日期：1997.9

  The synthesis of 1-(3,4,5-trimethoxyphenyl)-3-trialkylsiloxy-1,3-butadienes and their Diels-Alder reaction with selected dienophiles at room temperature is described. These aryldienes are useful building blocks for the synthesis of natural and pharmacological active products, as has been shown by the preparation of a tetracyclic ketone needed for the synthesis of new anthracycline analogues. (C) 1997 Elsevier Science Ltd.
• Open Analogues of Arcyriaflavin A. Synthesis through Diels−Alder Reaction between Maleimides and 1-Aryl-3-<i>tert</i>-butyldimethylsiloxy-1,3-butadienes
  作者：Marta Adeva、Heidi Sahagún、Esther Caballero、Rafael Peláez-Lamamié de Clairac、Manuel Medarde、Fernando Tomé

  DOI：10.1021/jo991815x

  日期：2000.6.1

  The preparation of a range of open analogues of arcyriaflavin A is described. The synthetic approach is based on the use of perhydroisoindole-1,3,5-triones as key intermediates, which were obtained via Diels-Alder methodology using 1-aryl-3-siloxy-1,3-butadienes as starting materials. Fischer indolization and aromatization processes afforded different methoxy-substituted arylpyrrolocarbazoles. The stereochemistry and conformation of the Diels-Alder products and the regiochemistry of the indolization reactions are supported by NMR and molecular modeling studies.