1-(4-溴-1H-吲哚-3-基)-2,2,2-三氯乙酮 | 1182349-06-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-(4-溴-1H-吲哚-3-基)-2,2,2-三氯乙酮
• 英文名称: 1-(4-bromo-1H-indol-3-yl)-2,2,2-trichloroethanone
• CAS: 1182349-06-9
• 化学式: C₁₀H₅BrCl₃NO
• 分子量: 341.419
• InChiKey: PRSVXXZKFFNSQA-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C (decomp)
• 沸点：
  434.0±40.0 °C(Predicted)
• 密度：
  1.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-溴-1H-吲哚-3-基)-2,2,2-三氯乙酮 在 水 、 potassium hydroxide 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以59%的产率得到4-溴-1H-吲哚-3-羧酸
  参考文献：
  名称：

  Drug Design, in Vitro Pharmacology, and Structure−Activity Relationships of 3-Acylamino-2-aminopropionic Acid Derivatives, a Novel Class of Partial Agonists at the Glycine Site on the N-Methyl-d-aspartate (NMDA) Receptor Complex

  摘要：

  Retaining agonistic activity at the glycine coagonist site of the NMDA receptor in molecules derived from glycine or D-serine has proven to be difficult because in the vicinity of the alpha-amino acid group little substitution is tolerated. We have solved this problem by replacing the hydroxy group of D-serine with an amido group, thus keeping the hydrogen donor function and allowing For further substitution and exploration of the adjacent space. Heterocyclic substitutions resulted in a series of 3-acylamino-2-aminopropionic acid derivatives, with high affinities in a binding assay for the glycine site. In a functional assay assessing the activation of the glycine site, these compounds displayed a wide range of intrinsic efficacies, from antagonism to a high degree of partial agonism. Structure-activity relationships reveal that lipophilic substituents, presumably filling an additional hydrophobic pocket, are accepted by the glycine site, provided that they are separated from the alpha-amino acid group by a short linker.

  DOI：

  10.1021/jm900363q
• 作为产物：
  描述：

  4-溴吲哚 、 三氯乙酰氯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 1-(4-溴-1H-吲哚-3-基)-2,2,2-三氯乙酮
  参考文献：
  名称：

  十钨酸盐光催化的吲哚脱芳烃加氢酰化：2-酰基二氢吲哚的直接合成

  摘要：

  “一个出乎意料的 POM”。在紫光照射下，十钨酸盐阴离子光催化吲哚的温和脱芳构化，通过直接氢原子转移获得 2-酰基二氢吲哚。

  DOI：

  10.1002/chem.202201707

文献信息

• Drug Design, in Vitro Pharmacology, and Structure−Activity Relationships of 3-Acylamino-2-aminopropionic Acid Derivatives, a Novel Class of Partial Agonists at the Glycine Site on the <i>N</i>-Methyl-<scp>d</scp>-aspartate (NMDA) Receptor Complex
  作者：Stephan Urwyler、Philipp Floersheim、Bernard L. Roy、Manuel Koller

  DOI：10.1021/jm900363q

  日期：2009.8.27

  Retaining agonistic activity at the glycine coagonist site of the NMDA receptor in molecules derived from glycine or D-serine has proven to be difficult because in the vicinity of the alpha-amino acid group little substitution is tolerated. We have solved this problem by replacing the hydroxy group of D-serine with an amido group, thus keeping the hydrogen donor function and allowing For further substitution and exploration of the adjacent space. Heterocyclic substitutions resulted in a series of 3-acylamino-2-aminopropionic acid derivatives, with high affinities in a binding assay for the glycine site. In a functional assay assessing the activation of the glycine site, these compounds displayed a wide range of intrinsic efficacies, from antagonism to a high degree of partial agonism. Structure-activity relationships reveal that lipophilic substituents, presumably filling an additional hydrophobic pocket, are accepted by the glycine site, provided that they are separated from the alpha-amino acid group by a short linker.
• Decatungstate‐Photocatalyzed Dearomative Hydroacylation of Indoles: Direct Synthesis of 2‐Acylindolines
  作者：Thomas Varlet、Damien Bouchet、Elsa Van Elslande、Géraldine Masson

  DOI：10.1002/chem.202201707

  日期：2022.10.7

  “A POM out of the blue”. Decatungstate anion photocatalyzed a mild dearomatization of indoles to access 2-acylindolines via direct hydrogen atom transfer under purple-light irradiation.

  “一个出乎意料的 POM”。在紫光照射下，十钨酸盐阴离子光催化吲哚的温和脱芳构化，通过直接氢原子转移获得 2-酰基二氢吲哚。