1-Iodo-2,4,5-trimethoxy-3-methyl-benzene | 185981-77-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Iodo-2,4,5-trimethoxy-3-methyl-benzene
• 英文别名: 1-Iodo-2,4,5-trimethoxy-3-methylbenzene
• CAS: 185981-77-5
• 化学式: C₁₀H₁₃IO₃
• 分子量: 308.116
• InChiKey: TYRGCMDKHQGQAS-UHFFFAOYSA-N

物化性质

• 沸点：
  334.0±42.0 °C(Predicted)
• 密度：
  1.542±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1-Iodo-2,4,5-trimethoxy-3-methyl-benzene 生成 2,4,5,2',4',5'-Hexamethoxy-3,3'-dimethyl-biphenyl
  参考文献：
  名称：

  Biaryl formation using the suzuki protocol: Considerations of base, halide, and protecting group.

  摘要：

  The generation of aryl anions prior to quenching with a trialkyl borate has been shown to be sensitive to the composition of the aryl substrate. Aryl iodides containing remote benzyl ether substituents undergo trans-metallation with sec-BuLi to cleanly give the desired aryl anions whereas the corresponding bromides afford appreciable quantities of dianionic intermediates. The arylboronic acids derived from alkylation of these anions subsequently undergo a palladium mediated coupling with aryl halides to provide good yields of the desired biaryls. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02065-5
• 作为产物：
  描述：

  2,4-二甲氧基-3-甲基苯酚 在 N-碘代丁二酰亚胺 、 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-Iodo-2,4,5-trimethoxy-3-methyl-benzene
  参考文献：
  名称：

  Biaryl formation using the suzuki protocol: Considerations of base, halide, and protecting group.

  摘要：

  The generation of aryl anions prior to quenching with a trialkyl borate has been shown to be sensitive to the composition of the aryl substrate. Aryl iodides containing remote benzyl ether substituents undergo trans-metallation with sec-BuLi to cleanly give the desired aryl anions whereas the corresponding bromides afford appreciable quantities of dianionic intermediates. The arylboronic acids derived from alkylation of these anions subsequently undergo a palladium mediated coupling with aryl halides to provide good yields of the desired biaryls. Copyright (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02065-5

文献信息

• Concise Synthesis of the CDE Ring System of Tetrahydroisoquinoline Alkaloids Using Carbophilic Lewis Acid-Catalyzed Hydroamidation and Oxidative Friedel−Crafts Cyclization
  作者：Shingo Obika、Yoshizumi Yasui、Reiko Yanada、Yoshiji Takemoto

  DOI：10.1021/jo800898k

  日期：2008.7.1

  A concise synthesis of the CDE ring system of the tetrahydroisoquinoline antitumor alkaloids such as saframycins, renieramycins, and ecteinascidins has been developed. Both Au(I)-catalyzed intramolecular hydroamidation of alkynylamide and NBS-mediated oxidative Friedel−Crafts cyclization of the resulting 2-ketopiperazine were utilized as key reactions.

  已经开发了四氢异喹啉抗肿瘤生物碱（如沙曲霉素，雷尼霉素和ecteinascidins）的CDE环系统的简明合成。Au（I）催化的炔基酰胺的分子内加氢酰胺化和NBS介导的氧化的Friedel-Crafts环化生成的2-ketopiperazine均被用作关键反应。