1-(4-iodophenyl)-2-(piperidin-1-yl)ethane-1,2-dione | 1269088-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-iodophenyl)-2-(piperidin-1-yl)ethane-1,2-dione
• 英文别名: 1-(4-iodophenylglyoxylyl)piperidine
• CAS: 1269088-44-9
• 化学式: C₁₃H₁₄INO₂
• 分子量: 343.164
• InChiKey: BKRYPEXCNXDZAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-iodophenyl)-2-(piperidin-1-yl)ethane-1,2-dione 、 对甲苯磺酰肼 在 硫酸 作用下， 以 乙醇 为溶剂， 以74%的产率得到N'-(1-(4-iodophenyl)-2-oxo-2-(piperidin-1-yl)ethylidene)-4-methylbenzenesulfonohydrazide
  参考文献：
  名称：

  Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling

  摘要：

  In contrast to tropane-based compounds such as benztropine and cocaine, non-tropane-based photo-affinity ligands for the dopamine transporter (DAT) are relatively unexplored. Towards addressing this knowledge gap, ligands were synthesized in which the piperidine nitrogen of 3- and 4-iodomethylphenidate was substituted with a benzyl group bearing a photoreactive azide. Analog (+/-)-3a demonstrated modest DAT affinity and a radioiodinated version was shown to bind covalently to rat striatal DAT and hDAT expressed in cultured cells. Co-incubation of (+/-)-3a with nonradioactive D-(+)-methylphenidate or (-)-2-beta-carbomethoxy-3-beta-(4-fluorophenyl) tropane (beta-CFT, WIN-35,428, a cocaine analog) blocked DAT labeling. Compound (+/-)-3a represents the first successful example of a DAT photoaffinity ligand based on the methylphenidate scaffold. Such ligands are expected to assist in mapping non-tropane ligand-binding pockets within plasma membrane monoamine transporters. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.002
• 作为产物：
  描述：

  哌啶 、 4-碘代苯乙酮 在 叔丁基过氧化氢 、 碘 作用下， 反应 8.0h， 以90%的产率得到1-(4-iodophenyl)-2-(piperidin-1-yl)ethane-1,2-dione
  参考文献：
  名称：

  TBHP/I2-promoted oxidative coupling of acetophenones with amines at room temperature under metal-free and solvent-free conditions for the synthesis of α-ketoamides

  摘要：

  一种新颖高效的TBHP/I2促进的醋酮与胺的氧化偶联反应已经被开发，用于合成α-酮酰胺。该反应在室温下以无金属和无溶剂的条件顺利进行，并生成了良好产率的相应产品。

  DOI：

  10.1039/c2gc35489f

文献信息

• NIS-Catalyzed Reactions: Amidation of Acetophenones and Oxidative Amination of Propiophenones
  作者：Manjunath Lamani、Kandikere Ramaiah Prabhu

  DOI：10.1002/chem.201202703

  日期：2012.11.12

  Single‐step amination: The N‐iodosuccinimide (NIS)‐catalyzed amidation of acetophenone derivatives by using tert‐butylhydroperoxide (TBHP) as an oxidant is presented. A variety of acetyl derivatives of heterocyclic compounds were easily converted to their corresponding ketoamides under these conditions. A new, NIS‐catalyzed amination of propiophenone and its derivatives in the presence of TBHP to furnish

  单步胺化：介绍了使用叔丁基过氧化氢（TBHP）作为氧化剂的N-碘琥珀酰亚胺（NIS）催化的苯乙酮衍生物酰胺化反应。在这些条件下，杂环化合物的各种乙酰基衍生物很容易转化为它们相应的酮酰胺。在TBHP存在下，一种新的NIS催化的苯乙酮及其衍生物的胺化反应可提供相应的2-氨基酮衍生物，这是首次报道的苯乙酮衍生物的单步胺化反应。