4-methyl-2-(p-methoxyphenyl)thiophene | 184355-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methyl-2-(p-methoxyphenyl)thiophene
• 英文别名: 2-(4-Methoxyphenyl)-4-methylthiophene
• CAS: 184355-40-6
• 化学式: C₁₂H₁₂OS
• 分子量: 204.293
• InChiKey: JVLPSKFPVPXPLP-UHFFFAOYSA-N

物化性质

• 熔点：
  66-68 °C
• 沸点：
  303.1±30.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(p-methoxyphenyl)thiophene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 1-[3-methyl-5-(p-methoxyphenyl)-2-thienyl]-2-[2-methyl-5-(p-methoxyphenyl)-3-thienyl]perfluorocyclopentene
  参考文献：
  名称：

  2,3-位杂二芳基乙烯衍生物的高效合成和光致变色性能

  摘要：

  提出了一种有效的合成方法，以合成一些2，3-位杂二芳基乙烯衍生物。在这些化合物中，噻吩环中的一个在2-位连接至乙烯部分，另一个在3-位连接至乙烯部分。这些不对称二芳烃在400和500 nm范围内的波长处敏感。它们可以在溶液中经历热不可逆和抗疲劳的光致变色反应，其中一些甚至在固态下也是如此。研究了取代基对其光致变色的影响。

  DOI：

  10.1016/s0040-4020(03)01141-4
• 作为产物：
  描述：

  4-溴苯甲醚 、 3-甲基噻吩 在 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 、 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以87%的产率得到4-methyl-2-(p-methoxyphenyl)thiophene
  参考文献：
  名称：

  C-H Arylation of 3-Substituted Thiophene with Regioselective Deprotonation by TMPMgCl·LiCl and Transition Metal Catalyzed Cross Coupling

  摘要：

  The reaction of 3-hexylthiophene with Knochel-Hauser base (TMPMgCl center dot LiCl) induced the metalation at the 5-position of the thiophene ring selectively. Following addition of several aryl halides in the presence of a nickel or palladium catalyst afforded regioselectively arylated thiophene in good to excellent yields.

  DOI：

  10.3987/com-12-s(n)6

文献信息

• Selective protodeboronation: synthesis of 4-methyl-2-thiopheneboronic anhydride and demonstration of its utility in Suzuki–Miyaura reactions
  作者：Liane M. Klingensmith、Matthew M. Bio、George A. Moniz

  DOI：10.1016/j.tetlet.2007.09.060

  日期：2007.11

  An efficient synthesis of 4-methyl-2-thiopheneboronic anhydride is reported. Regioselective lithiation of 3-methylthiophene followed by reaction with triisopropylborate and hydrolysis provides a 92:8 ratio of 4-methyl-2-thiopheneboronic acid (1) and regioisomeric 2-methyl-3-thiopheneboronic acid (3). The undesired regioisomer is selectively protodeboronated with concentrated acid to provide only the desired 4-methyl-2-thiopheneboronic acid (1). The title compound is isolated by dehydration/crystallization and employed in several Suzuki-Miyaura reactions. (C) 2007 Elsevier Ltd. All rights reserved.
• Substituent effect on the photochromic reactivity of bis(2-thienyl)perfluorocyclopentenes
  作者：Kingo Uchida、Toyokazu Matsuoka、Seiya Kobatake、Tadatsugu Yamaguchi、Masahiro Irie

  DOI：10.1016/s0040-4020(01)00389-1

  日期：2001.5

  Substituent effect on the photochromic reactivity of bis(2-thienyl)perfluorocyclopentenes was examined. introduction of phenyl groups having electron-donating substituents on the para-position of the phenyl ring to the 5-position of the thiophene rings shifted the absorption bands of the open-ring isomers to longer wavelengths and reduced the quantum yield of the cyclization reactions. The substitution with p-(N,N-diethylamino)phenyl groups prohibited the cyclization reaction. The absorption spectra of the closed-ring isomers were not influenced by the substitution. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Efficient synthesis and photochromic properties of 2,3-position hybrid diarylethene derivatives
  作者：Fan Sun、Fushi Zhang、Haobo Guo、Xinhong Zhou、Ruji Wang、Fuqun Zhao

  DOI：10.1016/s0040-4020(03)01141-4

  日期：2003.9

  An efficient synthetic method was proposed to synthesize some 2,3-position hybrid diarylethene derivatives. In these compounds, one of thiophene rings was attached to the ethylene moiety at 2-position, the other at 3-position. These asymmetric diarylethenes are sensitive at wavelengths in the region of 400 and 500 nm. They can undergo thermally irreversible and fatigue-resistant photochromic reactions

  提出了一种有效的合成方法，以合成一些2，3-位杂二芳基乙烯衍生物。在这些化合物中，噻吩环中的一个在2-位连接至乙烯部分，另一个在3-位连接至乙烯部分。这些不对称二芳烃在400和500 nm范围内的波长处敏感。它们可以在溶液中经历热不可逆和抗疲劳的光致变色反应，其中一些甚至在固态下也是如此。研究了取代基对其光致变色的影响。
• C-H Arylation of 3-Substituted Thiophene with Regioselective Deprotonation by TMPMgCl·LiCl and Transition Metal Catalyzed Cross Coupling
  作者：Atsunori Mori、Shunsuke Tamba、Atsushi Sugie、Shota Tanaka

  DOI：10.3987/com-12-s(n)6

  日期：——

  The reaction of 3-hexylthiophene with Knochel-Hauser base (TMPMgCl center dot LiCl) induced the metalation at the 5-position of the thiophene ring selectively. Following addition of several aryl halides in the presence of a nickel or palladium catalyst afforded regioselectively arylated thiophene in good to excellent yields.