2-Trimethylsilyl-6-(N,N-diethylcarbamoyl)-7-hydroxy-1-benzothiophene | 259817-26-0

• 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: 2-Trimethylsilyl-6-(N,N-diethylcarbamoyl)-7-hydroxy-1-benzothiophene
• 英文别名: N,N-diethyl-7-hydroxy-2-trimethylsilyl-1-benzothiophene-6-carboxamide
• CAS: 259817-26-0
• 化学式: C₁₆H₂₃NO₂SSi
• 分子量: 321.516
• InChiKey: JWAXHSMMMMVJPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  68.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Trimethylsilyl-6-(N,N-diethylcarbamoyl)-7-hydroxy-1-benzothiophene 在 仲丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N,N-diethyl-5-allyl-7-methoxy-2-trimethylsilylbenzo[b]thiophene-6-carboxamide
  参考文献：
  名称：

  Application of directed metallation in synthesis. Part 3: Studies in the synthesis of (±)-semivioxanthin and its analogues

  摘要：

  The synthesis of several analogues of (+/-)-semivioxanthin including five thiophene analogues, using directed metalation are reported. The strategy consisted of the synthesis of functionalized naphthalene or benzo[b]thiophene as building blocks followed by annelation of the pyrone. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01599-5
• 作为产物：
  描述：

  2-Trimethylsilyl-7-(N,N-diethylcarbamoyloxy)-1-benzothiophene 在 四甲基乙二胺 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以80%的产率得到2-Trimethylsilyl-6-(N,N-diethylcarbamoyl)-7-hydroxy-1-benzothiophene
  参考文献：
  名称：

  Studies in sulfur heterocycles. Part 16. Use of 7-hydroxy-1-benzothiophene in the synthesis of substituted benzothiophene derivatives and tricyclic compounds incorporating a fused thiophene ring

  摘要：

  异原子定向的邻位金属化反应应用于N,N-二乙基-7-氨基氧基-1-苯并噻唑，该化合物可通过7-羟基-1-苯并噻唑轻易获得，从而实现6位的区域选择性取代。7-羟基和4-羟基-1-苯并噻唑分别用于通过顺序的克莱森重排—闭环反应将5元或6元氧杂环连接到1-苯并噻唑分子上。连接环的性质取决于反应条件。

  DOI：

  10.1039/a904605d

文献信息

• Studies in sulfur heterocycles. Part 16. Use of 7-hydroxy-1-benzothiophene in the synthesis of substituted benzothiophene derivatives and tricyclic compounds incorporating a fused thiophene ring
  作者：Sukhen Chandra Ghosh、Asish De

  DOI：10.1039/a904605d

  日期：——

  Heteroatom directed ortho-metallation on N,N-diethyl-7-carbamoyloxy-1-benzothiophene, readily available from 7-hydroxy-1-benzothiophene enabled regioselective substitution in the 6-position. Both 7- and 4-hydroxy-1-benzothiophene were used in the annelation of 5- or 6-membered oxygen heterocycles onto the 1-benzothiophene molecule through sequential Claisen rearrangement–ring closure reactions. The nature of the annelated ring depends upon the reaction conditions.

  异原子定向的邻位金属化反应应用于N,N-二乙基-7-氨基氧基-1-苯并噻唑，该化合物可通过7-羟基-1-苯并噻唑轻易获得，从而实现6位的区域选择性取代。7-羟基和4-羟基-1-苯并噻唑分别用于通过顺序的克莱森重排—闭环反应将5元或6元氧杂环连接到1-苯并噻唑分子上。连接环的性质取决于反应条件。
• Application of directed metallation in synthesis. Part 3: Studies in the synthesis of (±)-semivioxanthin and its analogues
  作者：Sukanta Kamila、Chandrani Mukherjee、Sasanka S Mondal、Asish De

  DOI：10.1016/s0040-4020(02)01599-5

  日期：2003.2

  The synthesis of several analogues of (+/-)-semivioxanthin including five thiophene analogues, using directed metalation are reported. The strategy consisted of the synthesis of functionalized naphthalene or benzo[b]thiophene as building blocks followed by annelation of the pyrone. (C) 2003 Elsevier Science Ltd. All rights reserved.