(2,5-dibromothiophen-3-yl)(phenyl)methanol | 941609-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (2,5-dibromothiophen-3-yl)(phenyl)methanol
• 英文别名: 2,5-dibromo-α-phenyl-3-thiophenemethanol；(2,5-Dibromothiophen-3-yl)-phenylmethanol
• CAS: 941609-28-5
• 化学式: C₁₁H₈Br₂OS
• 分子量: 348.058
• InChiKey: VXAPCAOXBYBVQW-UHFFFAOYSA-N

物化性质

• 沸点：
  424.6±40.0 °C(Predicted)
• 密度：
  1.842±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2,5-dibromothiophen-3-yl)(phenyl)methanol 、 烯丙醇 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以61%的产率得到3-((allyloxy)(phenyl)methyl)-2,5-dibromothiophene
  参考文献：
  名称：

  三氟化硼·二乙基醚催化的醇醚化：无金属合成二苯甲基醚的途径

  摘要：

  已开发出一种新颖的三氟化硼·二乙醚（BF 3· OEt 2）催化的醚化方法，其中伯醇和仲醇易于转化为二苯甲基醚，收率高达99％。

  DOI：

  10.1002/adsc.201500663
• 作为产物：
  描述：

  溴甲苯 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 水 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 氯仿 、 水 为溶剂， 反应 7.0h， 生成 (2,5-dibromothiophen-3-yl)(phenyl)methanone 、 (2,5-dibromothiophen-3-yl)(phenyl)methanol
  参考文献：
  名称：

  Synthesis of structurally diverse diarylketones through the diarylmethyl sp3 CH oxidation

  摘要：

  Under open-flask conditions, an efficient method to assemble a series of diversely functionalized diarylketones in the presence of commercially available NBS has been developed. Yields of up to 99% have been achieved employing diarylmethanes as starting material. Based on O-18-labeled experiment, the addition of stoichiometric water eventually leads to excellent yields in all carbonylation cases. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.047

文献信息

• Trapping of Transient Thienyllithiums Generated by Deprotonation of 2,3- or 2,5-Dibromothiophene in a Flow Microreactor
  作者：Kentaro Okano、Yoshiki Yamane、Aiichiro Nagaki、Atsunori Mori

  DOI：10.1055/s-0040-1706479

  日期：2020.12

  Selective trapping of (4,5-dibromo-2-thienyl)lithium, known to undergo halogen dance, was achieved in a flow microreactor. This transient thienyllithium, generated by mixing 2,3-dibromothiophene and lithium diisopropylamide at –78 °C for 1.6 seconds, reacted with benzaldehyde. The reaction system is also applicable to other carbonyl compounds to afford the corresponding adducts in good yields. Moreover

  （4,5-二溴-2-噻吩基）锂的选择性捕获，已知会发生卤素舞蹈，是在流动微反应器中实现的。这种瞬态噻吩基锂是通过在 –78 °C 下将 2,3-二溴噻吩和二异丙基氨基锂混合 1.6 秒而生成的，它与苯甲醛反应。该反应体系也适用于其他羰基化合物，以良好的收率得到相应的加合物。此外，既定条件允许 2,5-二溴噻吩转化为两种结构异构体的混合物。对比结果根据反应途径进行讨论。
• Boron Trifluoride⋅Diethyl Ether-Catalyzed Etherification of Alcohols: A Metal-Free Pathway to Diphenylmethyl Ethers
  作者：Jiaqiang Li、Xiaohui Zhang、Hang Shen、Qing Liu、Jing Pan、Wen Hu、Yan Xiong、Changguo Chen

  DOI：10.1002/adsc.201500663

  日期：2015.10.12

  A novel boron trifluoride⋅diethyl ether (BF3⋅OEt2)-catalyzed etherification procedure has been developed in which primary and secondary alcohols are easily converted into diphenylmethyl ethers with yields of up to 99%.

  已开发出一种新颖的三氟化硼·二乙醚（BF 3· OEt 2）催化的醚化方法，其中伯醇和仲醇易于转化为二苯甲基醚，收率高达99％。
• Synthesis of structurally diverse diarylketones through the diarylmethyl sp3 CH oxidation
  作者：Chao He、Xiaohui Zhang、Ruofeng Huang、Jing Pan、Jiaqiang Li、Xuege Ling、Yan Xiong、Xiangming Zhu

  DOI：10.1016/j.tetlet.2014.06.047

  日期：2014.8

  Under open-flask conditions, an efficient method to assemble a series of diversely functionalized diarylketones in the presence of commercially available NBS has been developed. Yields of up to 99% have been achieved employing diarylmethanes as starting material. Based on O-18-labeled experiment, the addition of stoichiometric water eventually leads to excellent yields in all carbonylation cases. (C) 2014 Elsevier Ltd. All rights reserved.