6-(2-iodophenoxy)hexanoic acid | 1236230-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(2-iodophenoxy)hexanoic acid
• 英文别名: 6-(2-Iodo-phenoxy)-hexanoic acid
• CAS: 1236230-64-0
• 化学式: C₁₂H₁₅IO₃
• 分子量: 334.154
• InChiKey: YPUNXEQHRJUREK-UHFFFAOYSA-N

物化性质

• 沸点：
  435.6±30.0 °C(Predicted)
• 密度：
  1.571±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(2-iodophenoxy)hexanoic acid 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 N-(2-(N,N-diethylamino)ethyl)-6-(6-(2-iodophenoxy)hexanamido)quinoxaline-2-carboxamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Quinoxaline Derivatives of ICF01012 as Melanoma-Targeting Probes

  摘要：

  The aim of this study was the synthesis and pharmacokinetic selection of a best melanin-targeting ligand for addressing anticancer agents to pigmented melanoma. Seven quinoxaline carboxamide derivatives were synthesized and radiolabeled with iodine-125. Biodistribution studies of compounds [I-125]1a-g performed in melanoma-bearing mice tumor showed significant tumor uptake (range 2.43-5.68%ID/g) within 1 h after i.v. injection. Fast clearance of the radioactivity from the nontarget organs mainly via the urinary system gave high tumor-to-blood and tumor-to-muscle ratios. Given its favorable clearance and high tumor-melanoma uptake at 72 h, amide 1d was the most promising melanoma-targeting ligand in this series. Compound Id will be used as building block for the design of new melanoma-selective drug delivery systems.

  DOI：

  10.1021/ml400468x
• 作为产物：
  描述：

  ethyl 6-(2-iodophenoxy)hexanoic acid 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 生成 6-(2-iodophenoxy)hexanoic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Quinoxaline Derivatives of ICF01012 as Melanoma-Targeting Probes

  摘要：

  The aim of this study was the synthesis and pharmacokinetic selection of a best melanin-targeting ligand for addressing anticancer agents to pigmented melanoma. Seven quinoxaline carboxamide derivatives were synthesized and radiolabeled with iodine-125. Biodistribution studies of compounds [I-125]1a-g performed in melanoma-bearing mice tumor showed significant tumor uptake (range 2.43-5.68%ID/g) within 1 h after i.v. injection. Fast clearance of the radioactivity from the nontarget organs mainly via the urinary system gave high tumor-to-blood and tumor-to-muscle ratios. Given its favorable clearance and high tumor-melanoma uptake at 72 h, amide 1d was the most promising melanoma-targeting ligand in this series. Compound Id will be used as building block for the design of new melanoma-selective drug delivery systems.

  DOI：

  10.1021/ml400468x

文献信息

• Facile Benzo-Ring Construction via Palladium-Catalyzed Functionalization of Unactivated sp³ C−H Bonds under Mild Reaction Conditions
  作者：Yiqing Feng、Yuji Wang、Bradley Landgraf、Shi Liu、Gong Chen

  DOI：10.1021/ol101220x

  日期：2010.8.6

  methylene C−H bond is described. The palladium-catalyzed C−H functionalization is directed by an aminoquinoline carboxamide group, which can be easily installed and removed. High yields and broad substrate scope were achieved. An additive of ortho-phenyl benzoic acid, identified from a systematic screening, functions as a critical ligand for the catalytic process under mild condition, even at near room temperature

  描述了一种通过芳基碘化物和亚甲基CH键分子内偶联使苯环环化的实用合成方法。钯催化的CH官能团由氨基喹啉羧酰胺基团控制，该基团易于安装和拆卸。实现了高产量和广泛的基板范围。通过系统筛选确定的邻苯基苯甲酸添加剂可在温和条件下，甚至在室温下，作为催化过程的关键配体。