N-(2-chloroethyl)furan-2-carboxamide | 63003-69-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-chloroethyl)furan-2-carboxamide
• 英文别名: N-(2-Chloroethyl)-2-furamide
• CAS: 63003-69-0
• 化学式: C₇H₈ClNO₂
• 分子量: 173.599
• InChiKey: FWFRKOQCZMBNKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-chloroethyl)furan-2-carboxamide 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.0h， 生成 N-(2-(1,1,3,3-tetraoxidobenzo[d][1,3,2]dithiazol-2-yl)ethyl)furan-2-carboxamide
  参考文献：
  名称：

  通过 2-恶唑啉与酸性磺酰亚胺亲核试剂的开环磺酰亚胺化

  摘要：

  发现酸性磺酰亚胺亲核试剂包括二苯磺酰亚胺、邻苯磺酰亚胺、二甲磺酰亚胺和 N-（甲基磺酰基）-苯磺酰胺可打开各种烷基-、芳基杂芳基-2-恶唑啉环，以在回流 1,4-二恶烷中提供磺酰亚胺化产物. 富电子 2-恶唑线底物适用于亲核开环反应，而缺电子 2-恶唑啉底物没有发生反应。

  DOI：

  10.3998/ark.5550190.p009.609
• 作为产物：
  描述：

  糠酸（呋喃甲酸） 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.17h， 生成 N-(2-chloroethyl)furan-2-carboxamide
  参考文献：
  名称：

  Chemoselective (Hetero)Arene Electroreduction Enabled by Rapid Alternating Polarity

  摘要：

  DOI：

  10.1021/jacs.2c02102

文献信息

• One-pot triflic anhydride-mediated synthesis of 1,2-disubstituted 2-imidazolines from N-(2-haloethyl)amides and amines
  作者：Alyssa A. Ellsworth、Christina L. Magyar、Grace E. Hubbell、Chelsea C. Theisen、Daniel Holmes、R. Adam Mosey

  DOI：10.1016/j.tet.2016.08.040

  日期：2016.10

  A one-pot synthesis of 1,2-disubstituted 2-imidazolines from N-(2-haloethyl)amides has been developed. The reaction affords high yields of diverse 1,2-disubstituted 2-imidazolines from triflic anhydride-mediated dehydration of amides followed by installation of a primary amine.

  已经开发了由N-（2-卤代乙基）酰胺一锅合成1，2-二取代的2-咪唑啉。该反应从三氟甲磺酸酐介导的酰胺脱水，然后安装伯胺的方法中，可得到高产率的各种1,2-二取代的2-咪唑啉。
• Thionation ofN-(?-Halogenoalkyl)-Substituted Amides withLawesson's Reagent: Facile Synthesis of 4,5-Dihydro-1,3-thiazoles and 5,6-Dihydro-4H-1,3-thiazines
  作者：Yasuhiro Kodama、Mayuko Ori、Takehiko Nishio

  DOI：10.1002/hlca.200590000

  日期：2005.2

  The thionation and cyclization of N-(ω-halogenoalkyl)-substituted amides (and related compounds) with Lawesson's reagent (LR=2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide) has been investigated. Treatment of the amides 1 with LR gave the corresponding thioamides 2 in moderate to good yields (Table). The latter, upon treatment with base, afforded, either in a separate step or in

  的硫化和环化Ñ（ - ω -halogenoalkyl） -取代酰胺（和相关化合物）与劳森氏试剂（LR = 2,4-双（4-甲氧基苯基）-1,3,2,4-二硫2， 4-二硫化物）已被研究。用LR处理酰胺1，以中等至良好的产率得到相应的硫代酰胺2（表）。后者在用碱处理后，在单独的步骤或一锅法中得到环化的标题化合物，即4,5-二氢-1,3-噻唑3或相应的5-6-二氢-4 H-噻嗪4通过脱卤化氢反应。
• N-[(1-piperidinyl)alkyl]arylcarboxamide derivatives
  申请人：Janssen Pharmaceutica N.V.

  公开号：US04031226A1

  公开（公告）日：1977-06-21

  Compounds of the class of N-[(1-piperidinyl)alkyl]arylcarboxamides, useful as antiemetic and psychotropic agents.

  这是一种N-[(1-哌啶基)烷基]芳基羧酰胺类化合物，可用作抗恶心和精神药物。
• Structure-activity relationships in prazosin-related compounds. Effect of replacing a piperazine ring with an alkanediamine moiety on .alpha.1-adrenoreceptor blocking activity
  作者：Dario Giardina、Livio Brasili、Maurizio Gregori、Maurizio Massi、Maria T. Picchio、Wilma Quaglia、Carlo Melchiorre

  DOI：10.1021/jm00121a011

  日期：1989.1

  Several prazosin-related compounds were synthesized in which the piperazine ring of prazosin (1) was replaced by an alkanediamine chain and were evaluated for their blocking activity on alpha 1- and alpha 2-adrenoreceptors in isolated rat vas deferens. All the compounds investigated proved highly selective toward the alpha 1-adrenoreceptor owing to a very low affinity for alpha 2-adrenoreceptors. Furthermore, compounds 2, 9, and 13 were also investigated in vivo to determine their hypotensive effect on anesthetized rats, which were compared with that of prazosin (1). It was confirmed that the piperazine moiety of 1 is not essential for potency. However, optimum activity depends on two parameters: carbon-chain length of the alkanediamine moiety and N-methylation of both the amide and the 2-amino functions. In the desmethyl series, optimum activity was associated with the lower homologues (2-4) bearing a chain of two to four methylenes whereas in the N,N'-dimethyl series peak potency was observed with a six-carbon chain as in 13. Compound 13 proved the most active of the series and was more potent than prazosin (1) in both in vivo and in vitro assays. It is hypothesized that the alpha 1-adrenoreceptor incorporates a lipophilic area that is located between the binding sites for the quinazoline and the furoyl moieties and is able to accommodate a polymethylene chain.
• Poindexter, Graham S., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1431 - 1433
  作者：Poindexter, Graham S.

  DOI：——

  日期：——