1-(3,5-二溴噻吩-2-基)环己烷-1-醇 | 88089-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 1-(3,5-二溴噻吩-2-基)环己烷-1-醇
• 英文名称: 1-(3,5-Dibromothiophen-2-yl)cyclohexan-1-ol
• CAS: 88089-21-8
• 化学式: C₁₀H₁₂Br₂OS
• 分子量: 340.079
• InChiKey: YYTNHWCIVAPHFD-UHFFFAOYSA-N

物化性质

• 沸点：
  163-167 °C(Press: 3 Torr)
• 密度：
  1.809±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴噻吩 、 环己酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到1-(3,5-二溴噻吩-2-基)环己烷-1-醇
  参考文献：
  名称：

  First example of base-promoted tandem alkylation–bromination of 2-bromothiophene via halogen dance process: a remarkable temperature effect

  摘要：

  Metalation-alkylation of 2-bromothiophene 1 when conducted at low temperature led to the 5-alkylated 2-bromo products 2. While, at room temperature, the same sequential reactions afforded the original dibrorno-alkylated thiophenes 3 following an unprecedented halogen transfer-based halogen dance process in highly regiocontrolled and ordered way. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.109

文献信息

• Synthesis of 2-Substituted 3,5-Dibromothiophenes via a Rearrangement Reaction: A New Example of a Base-Catalyzed Halogen Dance Reaction
  作者：Fritz Sauter、Hannes Fröhlich、Wolfram Kalt

  DOI：10.1055/s-1989-27391

  日期：——

  The reaction of 2,3-dibromothiophene with 1 equivalent of lithium diisopropylamide at -80°C, followed by addition of an electrophile (methyl iodide, methanol, allyl bromide, dimethylformamide, cyclohexanone) gives 2-substituted 3,5-dibromothiophenes selectively and in high yields. The substitution pattern of all products was confirmed by unambiguous assignment of all C-atoms via 13C-NMR spectrometry.

  在 -80°C 下，2,3-二溴噻吩与 1 个等量的二异丙基酰胺锂发生反应，然后加入亲电体（甲基碘、甲醇、烯丙基溴、二甲基甲酰胺、环己酮），可选择性地高产出 2-取代的 3,5-二溴噻吩。通过 13C-NMR 光谱法对所有 C 原子进行明确分配，确认了所有产物的取代模式。
• Kano, Shinzo; Yuasa, Yoko; Yokomatsu, Tsutomu, Heterocycles, 1983, vol. 20, # 10, p. 2035 - 2037
  作者：Kano, Shinzo、Yuasa, Yoko、Yokomatsu, Tsutomu、Shibuya, Shiroshi

  DOI：——

  日期：——
• SAUTER, FRITZ;FROHLICH, HANNES;KALT, WOLFRAM, SYNTHESIS (BRD),(1989) N0, C. 771-773
  作者：SAUTER, FRITZ、FROHLICH, HANNES、KALT, WOLFRAM

  DOI：——

  日期：——
• KANO, SHINZO;YUASA, YOKO;YOKOMATSU, TSUTOMU;SHIBUYA, SHIROSHI, HETEROCYCLES, 1983, 20, N 10, 2035-2037
  作者：KANO, SHINZO、YUASA, YOKO、YOKOMATSU, TSUTOMU、SHIBUYA, SHIROSHI

  DOI：——

  日期：——
• First example of base-promoted tandem alkylation–bromination of 2-bromothiophene via halogen dance process: a remarkable temperature effect
  作者：Corinne Peyron、Jean-Michel Navarre、Nathalie Van Craynest、Rachid Benhida

  DOI：10.1016/j.tetlet.2005.03.109

  日期：2005.5

  Metalation-alkylation of 2-bromothiophene 1 when conducted at low temperature led to the 5-alkylated 2-bromo products 2. While, at room temperature, the same sequential reactions afforded the original dibrorno-alkylated thiophenes 3 following an unprecedented halogen transfer-based halogen dance process in highly regiocontrolled and ordered way. (c) 2005 Elsevier Ltd. All rights reserved.