(5-甲基-2-噻吩基)(氧代)乙酰氯 | 100005-44-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (5-甲基-2-噻吩基)(氧代)乙酰氯
• 英文名称: (5-Methylthiophen-2-yl)(oxo)acetyl chloride
• 英文别名: 2-(5-methylthiophen-2-yl)-2-oxoacetyl chloride
• CAS: 100005-44-5
• 化学式: C₇H₅ClO₂S
• 分子量: 188.635
• InChiKey: VGISDLCTBUGNAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯苯乙胺 、 (5-甲基-2-噻吩基)(氧代)乙酰氯 在 三乙胺 作用下， 以 苯 为溶剂， 以65%的产率得到N-[2-(4-chlorophenyl)ethyl]-2-(5-methylthiophen-2-yl)-2-oxoacetamide
  参考文献：
  名称：

  Isosteric replacement of the indole nucleus by benzothiophene and benzofuran in a series of indolylglyoxylylamine derivatives with partial agonist activity at the benzodiazepine receptor

  摘要：

  A number of benzothienyl- and benzofurylglyoxylylamine derivatives, which are analogues of previously described indolylglyoxylylamines with a partial agonist activity, are reported in this paper. They were synthesized and tested to verify the importance of the presence of the indole NH group in the interaction of this class of compounds with the benzodiazepine agonist receptor site, since it was reported in literature that a hydrogen bond donor group such as NH was not necessary to elicit an agonist response. Several thienylglyoxylylamine derivatives were also prepared and tested. None of the compounds showed a high affinity at the BzR, demonstrating that the indole NH plays a decisive role in the interaction of the agonist glyoxylylamine ligands with the receptor site.

  DOI：

  10.1016/s0223-5234(97)86173-9
• 作为产物：
  描述：

  (5-methyl-thiophen-2-yl)-oxo-acetic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (5-甲基-2-噻吩基)(氧代)乙酰氯
  参考文献：
  名称：

  Isosteric replacement of the indole nucleus by benzothiophene and benzofuran in a series of indolylglyoxylylamine derivatives with partial agonist activity at the benzodiazepine receptor

  摘要：

  A number of benzothienyl- and benzofurylglyoxylylamine derivatives, which are analogues of previously described indolylglyoxylylamines with a partial agonist activity, are reported in this paper. They were synthesized and tested to verify the importance of the presence of the indole NH group in the interaction of this class of compounds with the benzodiazepine agonist receptor site, since it was reported in literature that a hydrogen bond donor group such as NH was not necessary to elicit an agonist response. Several thienylglyoxylylamine derivatives were also prepared and tested. None of the compounds showed a high affinity at the BzR, demonstrating that the indole NH plays a decisive role in the interaction of the agonist glyoxylylamine ligands with the receptor site.

  DOI：

  10.1016/s0223-5234(97)86173-9

文献信息

• One-pot synthesis of heteroaryl diketoalkynyl C-glycoside and dialkynyl di-C-glycoside analogues by three-component successive coupling reaction
  作者：Xiang Zhou、Liming Wang、Fuyi Zhang、Yufen Zhao

  DOI：10.1016/j.carres.2023.108830

  日期：2023.7

  The synthesis of heteroaryl diketoalkynyl C-glycoside and dialkynyl di-C-glycoside analogues has been accomplished by successive coupling of heteroaromatics, oxalyl chloride and terminal sugar alkynes in one pot. The three-component coupling reaction catalyzed by CuI gives heteroaryl diketoalkynyl C-glycosides. The same three-component coupling in the presence of n-BuLi produces dialkynyl di-C-glycosides

  杂芳基二酮炔基C-糖苷和二炔基二-C-糖苷类似物的合成是通过在一锅中连续偶联杂芳烃、草酰氯和末端糖炔完成的。由 CuI 催化的三组分偶联反应得到杂芳基二酮炔基C-糖苷。在n-BuLi存在下同样的三组分偶联产生二炔基二-C-糖苷，杂芳烃与末端糖炔烃的摩尔比为1:1，得到相应的二炔基二-C-酯。-糖苷。以良好至极好的收率获得了所需的产品。这种顺序一锅法温和高效，适用于不同的杂芳烃和末端糖炔烃。糖炔烃包括呋喃糖苷、吡喃糖苷和无环糖。给出了二十七个例子。已经阐明了形成所需产物的机制。
• SUYAMA, TOSIXISA;KATO, SEDZO
  作者：SUYAMA, TOSIXISA、KATO, SEDZO

  DOI：——

  日期：——
• Isosteric replacement of the indole nucleus by benzothiophene and benzofuran in a series of indolylglyoxylylamine derivatives with partial agonist activity at the benzodiazepine receptor
  作者：F Da Settimo、A Lucacchini、AM Marini、C Martini、G Primofiore、G Senatore、S Taliani

  DOI：10.1016/s0223-5234(97)86173-9

  日期：1996.1

  A number of benzothienyl- and benzofurylglyoxylylamine derivatives, which are analogues of previously described indolylglyoxylylamines with a partial agonist activity, are reported in this paper. They were synthesized and tested to verify the importance of the presence of the indole NH group in the interaction of this class of compounds with the benzodiazepine agonist receptor site, since it was reported in literature that a hydrogen bond donor group such as NH was not necessary to elicit an agonist response. Several thienylglyoxylylamine derivatives were also prepared and tested. None of the compounds showed a high affinity at the BzR, demonstrating that the indole NH plays a decisive role in the interaction of the agonist glyoxylylamine ligands with the receptor site.