2-(2-iodobenzyl)cyclohexanone | 501346-71-0

• 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-iodobenzyl)cyclohexanone
• 英文别名: 2-(2-iodobenzyl)cyclohexan-1-one；2-[(2-Iodophenyl)methyl]cyclohexan-1-one
• CAS: 501346-71-0
• 化学式: C₁₃H₁₅IO
• 分子量: 314.166
• InChiKey: XFNDEBCSDQVUQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(2-iodobenzyl)cyclohexanone 在 高氯酸 、 乙二醇甲醚 、 (S)-(2-{3-[3,5-bis(trifluoromethyl)phenyl]thioureido}-3,3-dimethylbutyl)(naphthalen-1-ylmethyl)diphenylphosphonium bromide 、 sodium hydroxide 作用下， 以 四氯化碳 、 氯仿 、 水 、 均三甲苯 为溶剂， 反应 35.0h， 生成 2-(2-iodobenzyl)cyclohexan-1-one
  参考文献：
  名称：

  双功能Ph /硫脲催化剂对烯醇酯的对映选择性质子化

  摘要：

  衍生自叔亮氨酸的双官能phospho /硫脲可作为烯醇酯对映选择性质子化的高选择性催化剂，以高对映选择性（高达98.5：1.5 er）提供α-手性酮，收率高达99％。对照实验表明，大的叔丁基基团以及phospho和硫脲部分对于实现如此高的立体选择性是必需的。此外，机理研究表明，该催化剂已转化为相应的甜菜碱，可作为单分子催化剂。

  DOI：

  10.1021/acs.orglett.9b01216
• 作为产物：
  描述：

  methyl 1-(2-iodobenzyl)-2-oxocyclohexanecarboxylate 在 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以65%的产率得到2-(2-iodobenzyl)cyclohexanone
  参考文献：
  名称：

  Intramolecular Pd-Mediated Processes of Amino-Tethered Aryl Halides and Ketones:  Insight into the Ketone α-Arylation and Carbonyl-Addition Dichotomy. A New Class of Four-Membered Azapalladacycles

  摘要：

  An exploration of the scope and limitations of Pd(0)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from omega-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while (omega-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ketone alpha-arylation and carbonyl-addition in the reactions of omega-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.

  DOI：

  10.1021/ja029114w

文献信息

• Palladium-Catalyzed Cross-Coupling of Cyclopropanols with Aryl Halides Under Mild Conditions
  作者：David Rosa、Arturo Orellana

  DOI：10.1021/ol1026409

  日期：2011.1.7

  Intra- and intermolecular palladium-catalyzed cross-coupling of cyclopropanols with aryl halides can be achieved in good yields under mild conditions.

  在温和条件下，可以高收率实现环丙醇与芳基卤化物在分子内和分子间钯催化的交叉偶联。
• Transition-Metal-Free Site-Selective γ-C(sp²)–H Monoiodination of Arenes Directed by an Aliphatic Keto Group
  作者：Hong-Li Bian、Shi-Zhong Tang、Meng-En Chen、Xiao-Ming Zhang、Jian-Wei Lv、Xiao-Wei Chen、Feng-Ming Qi、Shi-Wu Chen、Fu-Min Zhang

  DOI：10.1021/acs.orglett.0c01466

  日期：2020.7.17

  A general gamma-C(sp(2))-H iodination method directed by an aliphatic keto group has been developed under transition-metal-free conditions for the first time, generating iodoarenes in good to excellent yields with excellent site selectivity. This protocol features a wide range of aryl-substituted ketones, short reaction times, mild reaction conditions, and scalable synthetic procedures. A possible reaction mechanism was also proposed based on several control experiments.