1-(5-chloro-2-methylthiophen-3-yl)-2-(2,5-dimethylthiophen-3-yl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-chloro-2-methylthiophen-3-yl)-2-(2,5-dimethylthiophen-3-yl)ethanone
• 英文别名: 1-(5-Chloro-2-methylthiophen-3-yl)-2-(2,5-dimethylthiophen-3-yl)ethanone
• 化学式: C₁₃H₁₃ClOS₂
• mdl: MFCD32223251
• 分子量: 284.831
• InChiKey: UBPTUYKSKYEUPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  73.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-chloro-2-methylthiophen-3-yl)-2-(2,5-dimethylthiophen-3-yl)ethanone 在 盐酸 、 ammonium acetate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 2-[5-(5-chloro-2-methylthiophen-3-yl)-3-cyano-4-(2,5-dimethylthiophen-3-yl)-5-hydroxy-1,5-dihydro-2H-pyrrol-2-ylidene]malononitrile
  参考文献：
  名称：

  在芳基取代的2-（3-氰基-5-羟基-1,5-二氢-2 H-吡咯-2-亚烷基）丙二腈的定向合成中4-氧代烷-1,1,2,2-四腈的重排

  摘要：

  通过2-芳基酮与四氰基乙烯的相互作用合成了3-芳基-4-氧代烷烃-1,1,2,2-四腈。在乙酸铵存在下，它们在乙酸中的直接重排导致形成具有芳基取代基的2-（3-氰基-5-羟基-1,5-二氢-2 H吡咯-2-亚烷基）丙二腈共轭形成与受体buta-1,3-diene-1,1,3-tricarbonitrile部分。

  DOI：

  10.1007/s10593-017-2170-1
• 作为产物：
  描述：

  2-氯-5-甲基噻吩 在 selenium(IV) oxide 、 四氯化锡 、 巯基乙酸甲酯 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 、 苯 为溶剂， 反应 15.5h， 生成 1-(5-chloro-2-methylthiophen-3-yl)-2-(2,5-dimethylthiophen-3-yl)ethanone
  参考文献：
  名称：

  Directed synthesis of new spiro-fused photochromes of diarylethene series

  摘要：

  The reaction of tetracyanoethylated 1,2-diarylethanones with morpholine was used for directed synthesis of spiro-fused diarylethenes, 8-amino-1-imino(oxo)-6-morpholino-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles. The intermediates in this process were tetracyanoalkanone salts. The formation of spiranes was sensitive to the nature of aromatic substituents at the carbonyl group of 3,4-diaryl-4-oxobutane-1,1,2,2-tetracarbonitriles. The obtained spiro-fused diarylethenes exhibited photochromic properties.

  DOI：

  10.1007/s10593-015-1731-4

文献信息

• Directed synthesis of new spiro-fused photochromes of diarylethene series
  作者：Mikhail Yu. Belikov、Mikhail Yu. Ievlev、Irina V. Belikova、Oleg V. Ershov、Viktor A. Tafeenko、Marina D. Surazhskaya

  DOI：10.1007/s10593-015-1731-4

  日期：2015.6

  The reaction of tetracyanoethylated 1,2-diarylethanones with morpholine was used for directed synthesis of spiro-fused diarylethenes, 8-amino-1-imino(oxo)-6-morpholino-2-oxa-7-azaspiro[4.4]nona-3,6,8-triene-9-carbonitriles. The intermediates in this process were tetracyanoalkanone salts. The formation of spiranes was sensitive to the nature of aromatic substituents at the carbonyl group of 3,4-diaryl-4-oxobutane-1,1,2,2-tetracarbonitriles. The obtained spiro-fused diarylethenes exhibited photochromic properties.
• Rearrangement of 4-oxoalkane-1,1,2,2-tetracarbonitriles in the directed synthesis of aryl-substituted 2-(3-cyano-5-hydroxy-1,5-dihydro-2H-pyrrol-2-ylidene)malononitriles
  作者：Mikhail Yu. Belikov、Sergey V. Fedoseev、Mikhail Yu. Ievlev、Oleg V. Ershov

  DOI：10.1007/s10593-017-2170-1

  日期：2017.9

  3-Aryl-4-oxoalkane-1,1,2,2-tetracarbonitriles were synthesized by the interaction of 2-aryl ketones with tetracyanoethylene. Directed rearrangement of them in acetic acid in the presence of ammonium acetate led to the formation of 2-(3-cyano-5-hydroxy-1,5-dihydro-2Hpyrrol-2-ylidene)malononitriles containing an aryl substituent in conjugation with the acceptor buta-1,3-diene-1,1,3-tricarbonitrile moiety

  通过2-芳基酮与四氰基乙烯的相互作用合成了3-芳基-4-氧代烷烃-1,1,2,2-四腈。在乙酸铵存在下，它们在乙酸中的直接重排导致形成具有芳基取代基的2-（3-氰基-5-羟基-1,5-二氢-2 H吡咯-2-亚烷基）丙二腈共轭形成与受体buta-1,3-diene-1,1,3-tricarbonitrile部分。