6-bromo-9-tert-butoxycarbonyl-1,4-dimethyl-9H-carbazole | 957783-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-bromo-9-tert-butoxycarbonyl-1,4-dimethyl-9H-carbazole
• 英文别名: 6-bromo-1,4-dimethyl-9-tert-butoxycarbonyl-9H-carbazole；tert-butyl 6-bromo-1,4-dimethyl-9H-carbazole-9-carboxylate；tert-Butyl 6-bromo-1,4-dimethyl-9H-carbazole-9-carboxylate；tert-butyl 6-bromo-1,4-dimethylcarbazole-9-carboxylate
• CAS: 957783-22-1
• 化学式: C₁₉H₂₀BrNO₂
• 分子量: 374.277
• InChiKey: PRAJFHFUOAIQHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromo-9-tert-butoxycarbonyl-1,4-dimethyl-9H-carbazole 在 正丁基锂 、 硼酸三甲酯 、 盐酸 作用下， 以 四氢呋喃 、 Petroleum ether 为溶剂， 反应 2.0h， 以60%的产率得到9-tert-butoxycarbonyl-5,8-dimethyl-9H-carbazole-3-boronic acid
  参考文献：
  名称：

  Novel and efficient synthesis of 5,8-dimethyl-9H-carbazol-3-ol via a hydroxydeboronation reaction

  摘要：

  N-Protected carbazol-3-yl-boronic acid derivatives have been efficiently hydroxydeboronated under mild conditions by employing hydrogen peroxide. The method allows to easily obtain 3-hydroxycarbazoles as precursors of new analogs of the anticancer agent 9-hydroxyellipticine.

  DOI：

  10.1016/s0385-5414(07)81095-1
• 作为产物：
  描述：

  6-bromo-1,4-dimethyl-9H-carbazole 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以63%的产率得到6-bromo-9-tert-butoxycarbonyl-1,4-dimethyl-9H-carbazole
  参考文献：
  名称：

  Novel and efficient synthesis of 5,8-dimethyl-9H-carbazol-3-ol via a hydroxydeboronation reaction

  摘要：

  N-Protected carbazol-3-yl-boronic acid derivatives have been efficiently hydroxydeboronated under mild conditions by employing hydrogen peroxide. The method allows to easily obtain 3-hydroxycarbazoles as precursors of new analogs of the anticancer agent 9-hydroxyellipticine.

  DOI：

  10.1016/s0385-5414(07)81095-1

文献信息

• Efficient and Simple Synthesis of 6-Aryl-1,4-dimethyl-9H-carbazoles
  作者：Anna Caruso、Anne Sophie Voisin-Chiret、Jean-Charles Lancelot、Maria Sinicropi、Antonio Garofalo、Sylvain Rault

  DOI：10.3390/molecules13061312

  日期：——

  A synthetic method for the preparation of 6-aryl-1,4-dimethyl-9H-carbazoles involving a palladium catalyzed coupling reaction of 1,4-dimethyl-9H-carbazole-6-boronic acids and (hetero)aryl halides is described.

  介绍了一种制备 6-芳基-1,4-二甲基-9H-咔唑的合成方法，该方法涉及 1,4-二甲基-9H-咔唑-6-硼酸和（杂）芳基卤化物的钯催化偶联反应。
• Synthesis of 2-TIPS-oxazol-5-ylboronic acid pinacol ester: efficient route to 5-(het)aryloxazoles via Suzuki cross-coupling reaction
  作者：Nicolas Primas、Alexandre Bouillon、Jean-Charles Lancelot、Sylvain Rault

  DOI：10.1016/j.tet.2009.06.023

  日期：2009.8

  A facile synthetic route to the new 2-TIPS PS-oxazol-5-ylboronic acid pinacol ester was described herein. Its reactivity toward Suzuki cross-coupling reaction was studied to provide various 5-(het)aryloxazoles. A wide range of functions on the aryl moiety are tolerated. (C) 2009 Elsevier Ltd. All rights reserved.
• Novel and efficient synthesis of 5,8-dimethyl-9H-carbazol-3-ol via a hydroxydeboronation reaction
  作者：A CARUSO、A VOISINCHIRET、J LANCELOT、M SINICROPI、A GAROFALO、S RAULT

  DOI：10.1016/s0385-5414(07)81095-1

  日期：2007.10.1

  N-Protected carbazol-3-yl-boronic acid derivatives have been efficiently hydroxydeboronated under mild conditions by employing hydrogen peroxide. The method allows to easily obtain 3-hydroxycarbazoles as precursors of new analogs of the anticancer agent 9-hydroxyellipticine.