methyl 3-(1-imidazolyl)crotonate | 92234-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 3-(1-imidazolyl)crotonate
• 英文别名: methyl β-(1-imidazolyl)crotonoate；methyl 3-(2H-imidazol-1-yl)but-2-enoate；Methyl 3-imidazol-1-ylbut-2-enoate
• CAS: 92234-51-0
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: JFTSUPKCUHWAAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-(1-imidazolyl)crotonate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 3-ethylsulfanyl-crotonic acid methyl ester
  参考文献：
  名称：

  Kashima, Choji; Tajima, Tadakuni; Omote, Yoshimori, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 171 - 176

  摘要：

  DOI：
• 作为产物：
  描述：

  咪唑 、 2,3-二溴丁酸甲酯 在 三乙胺 作用下， 生成 methyl 3-(1-imidazolyl)crotonate
  参考文献：
  名称：

  Kashima, Choji; Tajima, Tadakuni; Omote, Yoshimori, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 171 - 176

  摘要：

  DOI：

文献信息

• Regioselective synthesis of 3-hydroxyisoxazoles and 5-isoxazolones from β-amino α,β-unsaturated esters
  作者：Choji Kashima、Yumiko Konno、Nobutoshi Yoshiwara、Tadakuni Tajima

  DOI：10.1002/jhet.5570190657

  日期：1982.11

  regioselective synthesis of 3-hydroxyisoxazoles and 5-isoxazolones is accomplished by the reaction of β-amino α,β-unsaturated esters with hydroxylamine hydrochloride in the presence of appropriate bases. The total yield of isoxazole derivatives is sensitively influenced on the β-substituent group of the esters.

  在适当的碱存在下，通过β-氨基α，β-不饱和酯与羟胺盐酸盐的反应，可以完成3-羟基异恶唑和5-异恶唑酮的区域选择性合成。异恶唑衍生物的总收率对酯的β-取代基敏感。
• Kashima, Choji; Hibi, Shigeki; Shimizu, Masao, Heterocycles, 1986, vol. 24, # 2, p. 429 - 436
  作者：Kashima, Choji、Hibi, Shigeki、Shimizu, Masao、Tajima, Tadakuni、Omote, Yoshimori

  DOI：——

  日期：——
• A Thermal Cascade Route to Pyrroloisoindolone and Pyrroloimidazolones
  作者：Hamish McNab、Richard G. Tyas

  DOI：10.1021/jo0712502

  日期：2007.11.1

  Flash vacuum pyrolysis (FVP) of indol-1-ylacrylate derivatives 11 and 15 or the isomeric indol-3ylacrylates 21, 22, and 24 at 925 degrees C (0.05 Torr) provides pyrrolo[1,2-alpha]indol-3-ones 2, 18, 28, and 29 in 53-90% yield by a cascade mechanism that involves a sigmatropic migration, elimination, electrocyclization sequence. Pyrrolo[1,2-a]imidazol-5-ones 3 and pyrrolo[1,2-c]imidazol-5-ones 4 were similarly obtained by FVP of corresponding 2,5-unsubstituted imidazol-1-ylacrylates (e.g., 33), with the former isomer predominating in ca. 80:20 ratio. Migration to the 2-position is therefore favored in the initial sigmatropic shift. FVP of 2-substituted imidazol-1-ylacrylates 35, 37, and 51 (825-875 C) instead give pyrrolo[l,2-c]imidazol-5-ones 56-58 only (88-91%), and that of 4,5-disubstituted imidazol-1-ylacrylates 39 and 41 (825-850 degrees C) provide pyrrolo[1,2-a]imidazol-5-ones 59 and 60 exclusively (93-95%), and thus the selectivity of the initial shift can be controlled by the presence of substituents on the imidazole 2- and 5-positions. FVP of the benzimidazole analogues 61 and 62 at 950 C gave the pyrrolo[1,2-a]benzimidazol-l-ones 6 (71%) and 63 (36%), respectively.
• Kashima, Choji; Tsuzuki, Atsushi; Tajima, Tadakuni, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 201 - 203
  作者：Kashima, Choji、Tsuzuki, Atsushi、Tajima, Tadakuni

  DOI：——

  日期：——