N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)-2-iodobenzamide | 1374579-22-2

• 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: N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)-2-iodobenzamide
• CAS: 1374579-22-2
• 化学式: C₁₆H₁₆INO₂
• 分子量: 381.213
• InChiKey: NGKUIJCENZRINA-IAQYHMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)-2-iodobenzamide 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以43%的产率得到(4R,5R)-2-(2-iodophenyl)-4-methyl-5-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Catalytic Enantioselective α-Tosyloxylation of Ketones Using Iodoaryloxazoline Catalysts: Insights on the Stereoinduction Process

  摘要：

  A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated alpha-tosyloxylation of ketone derivatives. The alpha-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.

  DOI：

  10.1021/jo302393u
• 作为产物：
  描述：

  2-碘苯甲酸 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)-2-iodobenzamide
  参考文献：
  名称：

  Catalytic Enantioselective α-Tosyloxylation of Ketones Using Iodoaryloxazoline Catalysts: Insights on the Stereoinduction Process

  摘要：

  A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated alpha-tosyloxylation of ketone derivatives. The alpha-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.

  DOI：

  10.1021/jo302393u

文献信息

• Synthesis, fluorine-18 radiolabeling, and in vitro characterization of 1-iodophenyl-N-methyl-N-fluoroalkyl-3-isoquinoline carboxamide derivatives as potential PET radioligands for imaging peripheral benzodiazepine receptor
  作者：Weiping Yu、Eric Wang、Ronald J. Voll、Andrew H. Miller、Mark M. Goodman

  DOI：10.1016/j.bmc.2008.04.046

  日期：2008.6

  using in vitro competitive binding assays with [(3)H]PK11195 in rat kidney mitochondrial membranes. The results showed that the 1-(2-iodophenyl)-N-methyl-N-(3-fluoropropyl)-3-isoquinoline carboxamide (9a) was the most potent compound (K(i)=0.26nM) of this series and is an excellent lead ligand for additional studies for labeling with fluorine-18 to determine whether it possesses the desired in vivo performance

  已显示异喹啉羧酰胺衍生物1-（2-氯苯基）-N-甲基-N-（1-甲基丙基）-3-异喹啉羧酰胺（PK11195）与周围的苯二氮杂receptor受体（PBR）结合位点牢固且选择性地结合。已合成了一系列PK11195类似物并对其进行了生物学表征。使用[（3）H] PK11195在大鼠肾脏线粒体膜中进行体外竞争性结合测定，确定类似物对PBR的亲和力。结果表明，1-（2-碘苯基）-N-甲基-N-（3-氟丙基）-3-异喹啉羧酰胺（9a）是该系列中最有效的化合物（K（i）= 0.26nM），并且是用于进一步研究用氟18标记以确定其是否具有通过PET成像在非人灵长类动物中所需的体内表现的进一步研究的优秀铅配体。因此，