3-cyano-4,5-dihydro-2-thiopheneacetonitrile | 158553-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: 3-cyano-4,5-dihydro-2-thiopheneacetonitrile
• 英文别名: 5-(Cyanomethyl)-2,3-dihydrothiophene-4-carbonitrile
• CAS: 158553-78-7
• 化学式: C₇H₆N₂S
• 分子量: 150.204
• InChiKey: NFDNWKSXJFMZGY-UHFFFAOYSA-N

物化性质

• 沸点：
  323.8±42.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cyano-4,5-dihydro-2-thiopheneacetonitrile 在 sulfur 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以51%的产率得到4-amino-2,3-dihydrothieno[3,4-b]thiophene-6-carbonitrile
  参考文献：
  名称：

  Synthesis of Fused Thiopyranthione and Thiophene Derivatives from 4,5-Dihydro-3-thiophene(and -3-furan)carbonitriles Having an Active Methylene Group at C-2 Position

  摘要：

  A versatile strategy is described for the synthesis of new fused thiopyranthione and thiophene derivatives. The reaction of heterocyclic alpha,beta-unsaturated nitrites 3a-c, 4a-d, 5a-c, and 6a-d, which were prepared from tetrahydro-2-oxo-3-thiophene- and -3-furan-carbonitriles 1a-c and/or 2a-d and alkylidene phosphoranes such as (triphenylphosphoranylidene)acetonitrile and methyl (triphenylphosphoranylidene)acetate through Wittig reaction, with carbon disulfide in the presence of sodium hydride in THF gave the corresponding 6-thioxothieno[3,2-c]thiopyran and 6-thioxothiopyrano[4,3-b]furan derivatives 7a-c, 8a-d, 9a-c, and 10a-d. On the other hand, treatment of compounds 3a-c, 5a-c, and 6a-d with sulfur powder in the presence of triethylamine in methanol caused Gewald reaction to provide the corresponding thieno[3,4-b]thiophene and -furan derivatives 11a-c, 12a-c, and 13a-d.

  DOI：

  10.3987/com-09-11894
• 作为产物：
  描述：

  tetrahydro-2-oxo-3-thiophenecarbonitrile 、 (三苯基膦)乙腈 以 甲苯 为溶剂， 反应 8.0h， 以93%的产率得到3-cyano-4,5-dihydro-2-thiopheneacetonitrile
  参考文献：
  名称：

  Synthesis of Fused Thiopyranthione and Thiophene Derivatives from 4,5-Dihydro-3-thiophene(and -3-furan)carbonitriles Having an Active Methylene Group at C-2 Position

  摘要：

  A versatile strategy is described for the synthesis of new fused thiopyranthione and thiophene derivatives. The reaction of heterocyclic alpha,beta-unsaturated nitrites 3a-c, 4a-d, 5a-c, and 6a-d, which were prepared from tetrahydro-2-oxo-3-thiophene- and -3-furan-carbonitriles 1a-c and/or 2a-d and alkylidene phosphoranes such as (triphenylphosphoranylidene)acetonitrile and methyl (triphenylphosphoranylidene)acetate through Wittig reaction, with carbon disulfide in the presence of sodium hydride in THF gave the corresponding 6-thioxothieno[3,2-c]thiopyran and 6-thioxothiopyrano[4,3-b]furan derivatives 7a-c, 8a-d, 9a-c, and 10a-d. On the other hand, treatment of compounds 3a-c, 5a-c, and 6a-d with sulfur powder in the presence of triethylamine in methanol caused Gewald reaction to provide the corresponding thieno[3,4-b]thiophene and -furan derivatives 11a-c, 12a-c, and 13a-d.

  DOI：

  10.3987/com-09-11894

文献信息

• A Convenient Approach to the Synthesis of Novel Tricyclic Fused Furo[2,3-b]pyridine Derivatives
  作者：Fumi Okabe-Nakahara、Kazuhiro Tomoike、Hayate Nagabuchi、Eiichi Masumoto、Hiroshi Maruoka、Kenji Yamagata

  DOI：10.3987/com-19-14093

  日期：——

  – The synthesis of novel tricyclic fused furo[2,3-b]pyridine derivatives is described. 3-Cyano-4,5-dihydro-2-furan(and 2-thiophene)acetonitriles 1,2 were reacted with phenacyl bromides to give 5'-arylfuran-2'-amines 3,4. Compounds 3,4 were intramolecularly cyclized in the presence of sodium ethoxide to yield tricyclic fused furo[2,3-b]pyridine derivatives 5,6. Furthermore, one-pot synthesis of compounds

  摘要 - 描述了新型三环稠合呋​​喃[2,3-b]吡啶衍生物的合成。3-氰基-4,5-二氢-2-呋喃(和2-噻吩)乙腈1,2与苯酰溴反应得到5'-芳基呋喃-2'-胺3,4。化合物3,4在乙醇钠存在下进行分子内环化，得到三环稠合呋​​喃[2,3-b]吡啶衍生物5,6。此外，还开发了从起始材料 1,2 合成化合物 5,6 的一锅法。
• Yamagata, Kenji; Hashimoto, Yoshichika; Yamazaki, Motoyoshi, Liebigs Annalen der Chemie, 1994, # 8, p. 791 - 794
  作者：Yamagata, Kenji、Hashimoto, Yoshichika、Yamazaki, Motoyoshi

  DOI：——

  日期：——
• An Efficient Synthetic Route towards Novel Furo- and Thieno-triazolopyridines
  作者：Hiroshi Maruoka、Kazuhiro Tomoike、Fumi Okabe、Eiichi Masumoto、Toshihiro Fujioka、Kenji Yamagata

  DOI：10.3987/com-14-12931

  日期：——

  An efficient method for the synthesis of novel nitrogen-containing heterotricycles is described. 4,5-Dihydro-3-furan- and -3-thiophene-carbonitriles la,b and 2a,b having an active methylene group at C-2 position served as the precursor of enamines 3a,b and 4a,b, which were followed by an exchange reaction of amines, such as acetohydrazide and benzohydrazide, and subsequent tandem intramolecular cyclization reaction to lead the corresponding furo- and thieno-triazolopyridines 5a,b, 6a,b, 7a,b, and 8a,b.