4-(trimethylsilylbutadiynyl)phenol | 1426919-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(trimethylsilylbutadiynyl)phenol
• 英文别名: 4-(4-Trimethylsilylbuta-1,3-diynyl)phenol；4-(4-trimethylsilylbuta-1,3-diynyl)phenol
• CAS: 1426919-94-9
• 化学式: C₁₃H₁₄OSi
• 分子量: 214.339
• InChiKey: PTOCCHPJSNRZGU-UHFFFAOYSA-N

物化性质

• 熔点：
  59-60 °C
• 沸点：
  305.4±44.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(trimethylsilylbutadiynyl)phenol 、 1-己氧基-4-碘苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到4-[4-(4-Hexoxyphenyl)buta-1,3-diynyl]phenol
  参考文献：
  名称：

  Phenoxide-mediated Sonogashira coupling of trimethylsilylalkynes and aryliodides: practical synthesis of phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes

  摘要：

  We successfully synthesized phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes from trimethylsilylalkynes and aryliodides via silyl-group-migration-induced deprotection of alkynes and the usual Sonogashira coupling. The phenol moiety, which works as a desilylating agent, can be attached to any position in the coupling partner. This improvement for Sonogashira coupling would be highly effective, especially when the coupling partner has a phenol moiety. Additionally, the stability of the migrated silyl moiety on the ethynylation of 2-iodophenol is discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.091
• 作为产物：
  描述：

  1,4-双(三甲硅基)-1,3-丁二炔 、 4-碘苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以81%的产率得到4-(trimethylsilylbutadiynyl)phenol
  参考文献：
  名称：

  Phenoxide-mediated Sonogashira coupling of trimethylsilylalkynes and aryliodides: practical synthesis of phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes

  摘要：

  We successfully synthesized phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes from trimethylsilylalkynes and aryliodides via silyl-group-migration-induced deprotection of alkynes and the usual Sonogashira coupling. The phenol moiety, which works as a desilylating agent, can be attached to any position in the coupling partner. This improvement for Sonogashira coupling would be highly effective, especially when the coupling partner has a phenol moiety. Additionally, the stability of the migrated silyl moiety on the ethynylation of 2-iodophenol is discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.091

文献信息

• Phenoxide-mediated Sonogashira coupling of trimethylsilylalkynes and aryliodides: practical synthesis of phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes
  作者：Masayuki Shigeta、Junji Watanabe、Gen-ichi Konishi

  DOI：10.1016/j.tetlet.2013.01.091

  日期：2013.3

  We successfully synthesized phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes from trimethylsilylalkynes and aryliodides via silyl-group-migration-induced deprotection of alkynes and the usual Sonogashira coupling. The phenol moiety, which works as a desilylating agent, can be attached to any position in the coupling partner. This improvement for Sonogashira coupling would be highly effective, especially when the coupling partner has a phenol moiety. Additionally, the stability of the migrated silyl moiety on the ethynylation of 2-iodophenol is discussed. (C) 2013 Elsevier Ltd. All rights reserved.