2-(2-iodophenyl)-2-methylpropanoic acid | 1258494-28-8

• 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: 2-(2-iodophenyl)-2-methylpropanoic acid
• CAS: 1258494-28-8
• 化学式: C₁₀H₁₁IO₂
• 分子量: 290.101
• InChiKey: JZHZATJZIXIKMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-iodophenyl)-2-methylpropanoic acid 在 oxone(R) 作用下， 以 水 为溶剂， 反应 4.0h， 以73%的产率得到2-(2-iodylphenyl)-2-methylpropanoic acid
  参考文献：
  名称：

  6-Membered Pseudocyclic IBX Acids: Syntheses, X-ray Structural Characterizations, and Oxidation Reactivities in Common Organic Solvents

  摘要：

  We designed and synthesized lambda(5)-cyclic periodinanes 1 and 2, which are homologous to IBX (1-hydroxyl-oxo-1H-1 lambda(5)-benzo[d][1,2]iodoxol-3-one) by one carbon, to thwart close packing of molecules in the crystal lattice to permit solubility in common organic solvents and to facilitate oxidations with enhanced reactivity. The X-ray crystal structures revealed that both 1 and 2 exist in the solid state as pseudocyclic (PC) acids, i.e., 1PC and 2PC, and that the molecules in the lattice are less weakly associated as compared to those in the parent IBX due to the twisting introduced via the sp(3) benzylic carbon. Both 1PC and 2PC are found to dissolve in palpable amounts in DCM and acetonitrile to allow oxidation of a variety of alcohols and sulfides to carbonyl compounds and sulfoxides in a facile manner. The subtle differences in the sterics due to methyl and ethyl substituents in 1PC and 2PC are found to manifest in contrasting reactivities in that the oxidations of alcohols occur faster with 2PC, while those of sulfides to sulfoxides occur more rapidly with 1PC.

  DOI：

  10.1021/jo101639j
• 作为产物：
  描述：

  2-o-iodophenyl-2-methylpropanenitrile 在 硫酸 、 sodium nitrite 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 4.0h， 以82%的产率得到2-(2-iodophenyl)-2-methylpropanoic acid
  参考文献：
  名称：

  6-Membered Pseudocyclic IBX Acids: Syntheses, X-ray Structural Characterizations, and Oxidation Reactivities in Common Organic Solvents

  摘要：

  We designed and synthesized lambda(5)-cyclic periodinanes 1 and 2, which are homologous to IBX (1-hydroxyl-oxo-1H-1 lambda(5)-benzo[d][1,2]iodoxol-3-one) by one carbon, to thwart close packing of molecules in the crystal lattice to permit solubility in common organic solvents and to facilitate oxidations with enhanced reactivity. The X-ray crystal structures revealed that both 1 and 2 exist in the solid state as pseudocyclic (PC) acids, i.e., 1PC and 2PC, and that the molecules in the lattice are less weakly associated as compared to those in the parent IBX due to the twisting introduced via the sp(3) benzylic carbon. Both 1PC and 2PC are found to dissolve in palpable amounts in DCM and acetonitrile to allow oxidation of a variety of alcohols and sulfides to carbonyl compounds and sulfoxides in a facile manner. The subtle differences in the sterics due to methyl and ethyl substituents in 1PC and 2PC are found to manifest in contrasting reactivities in that the oxidations of alcohols occur faster with 2PC, while those of sulfides to sulfoxides occur more rapidly with 1PC.

  DOI：

  10.1021/jo101639j

文献信息

• Stereospecific Synthesis of Tetrahydronaphtho[2,3-<i>b</i>]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization
  作者：Yu Peng、Jian Xiao、Xiao-Bo Xu、Shu-Ming Duan、Li Ren、Yong-Liang Shao、Ya-Wen Wang

  DOI：10.1021/acs.orglett.6b02665

  日期：2016.10.7

  toward new analogues of therapeutic agents (iso)deoxypodophyllotoxin are also reported. In addition, the inherent substrate control is disclosed for the observed unique stereoselectivities during cyclizations.

  首次有效地实现了镍介导的反式四氢萘并[2,3- b ]呋喃立体选择性合成的级联反应。温和的还原体系可以容易地由廉价且空气稳定的材料产生，并显示出以前很难或不可能通过其他方法获得的取代基的宽位置耐受性。还报道了易于合成新的治疗剂（异）脱氧鬼臼毒素的类似物。另外，公开了固有的底物控制用于环化过程中观察到的独特立体选择性。