1-Chloro-3-(cyclobutylidenemethyl)benzene | 1114779-88-2

• 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: 1-Chloro-3-(cyclobutylidenemethyl)benzene
• CAS: 1114779-88-2
• 化学式: C₁₁H₁₁Cl
• 分子量: 178.661
• InChiKey: SXOUVPFFDDZDTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-Chloro-3-(cyclobutylidenemethyl)benzene 在 ammonium cerium (IV) nitrate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以64%的产率得到3-(3-Chlorophenyl)-1,2-dioxaspiro[3.3]heptane
  参考文献：
  名称：

  Cerium(IV) Ammonium Nitrate–Mediated Oxidation of Mono-aryl-substituted Methylenecyclobutanes: A Convenient Method for the Synthesis of Spirocyclobutyl-1,2-dioxethanes

  摘要：

  Cerium(IV) ammonium nitrate (CAN)-mediated oxidation of methylenecyclobutanes was investigated. Compared with the similar reactions of methylenecyclopropanes, the reaction products were quite different. Instead of the desired ring-enlarged product cyclopentanones, a cyclobutyl ring-intact product, spirocyclobutyl-1,2-dioxethane, was obtained. The structures of these spiroheterocycle-containing compounds are interesting, and the reactions are potentially valuable in both organic synthesis and mechanism research.

  DOI：

  10.1080/00397911.2010.505705

文献信息

• Reactions of Monoaryl-Substituted Methylenecyclobutanes and Methylenecyclopropanes with 1-Hydroxybenzotriazole (HOBt), 1-Hydroxy-7-azabenzotriazole (HOAt), and 1-Hydroxysuccinimide (HOSu)
  作者：Min Jiang、Min Shi

  DOI：10.1021/jo9000299

  日期：2009.3.20

  Monoaryl-substituted methylenecyclobutanes (MCBs) and methylenecyclopropanes (MCPs) react with 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu) smoothly to produce the corresponding cyclobutylmethanone and cyclopropylmethanone derivatives 2, 4, and 5 via a cascade epoxidation and nucleophilic addition process or the corresponding epoxides 6 in moderate

  单芳基取代的亚甲基环丁烷（MCB）和亚甲基环丙烷（MCP）与1-羟基苯并三唑（HOBt），1-羟基-7-氮杂苯并三唑（HOAt）和1-羟基琥珀酰亚胺（HOSu）平稳反应，生成相应的环丁基甲酮和环丙基甲酮衍生物2，通过级联环氧化和亲核加成过程或相应的环氧化物6在温和的条件下以中等至良好的收率得到图4和5所示的产物。在控制实验和反应中间体的分离的基础上，提出了一种合理的机理。
• The reaction of mono-aryl substituted methylenecyclobutanes with diphenyl diselenide in the presence of iodosobenzene diacetate and H2O
  作者：Min Jiang、Min Shi

  DOI：10.1016/j.tet.2008.11.052

  日期：2009.1

  The mono-aryl substituted methylenecyclobutanes undergo an interesting reaction with diphenyl diselenide in the presence of iodosobenzene diacetate and H2O at 40 °C in 1,2-dichloroethane to give the corresponding aryl-(1-phenylselanylcyclobutyl)methanones in moderate to good yields within 30 h. A plausible reaction mechanism has been discussed on the basis of the control and 18O-labeling experiments

  单芳基取代的亚甲基环丁烷在碘代苯二乙酸酯和H 2 O的存在下，在40°C下于1,2-二氯乙烷中与二苯二硒化物进行有趣的反应，从而以中等至良好的收率得到相应的芳基-（1-苯基硒基环丁基）甲酮。 30小时内。在控制和18 O-标记实验的基础上，已经讨论了可能的反应机理。
• Cerium(IV) Ammonium Nitrate–Mediated Oxidation of Mono-aryl-substituted Methylenecyclobutanes: A Convenient Method for the Synthesis of Spirocyclobutyl-1,2-dioxethanes
  作者：Lei Yu、Lingfeng Ren、Rong Yi、Rong Guo

  DOI：10.1080/00397911.2010.505705

  日期：2011.9.1

  Cerium(IV) ammonium nitrate (CAN)-mediated oxidation of methylenecyclobutanes was investigated. Compared with the similar reactions of methylenecyclopropanes, the reaction products were quite different. Instead of the desired ring-enlarged product cyclopentanones, a cyclobutyl ring-intact product, spirocyclobutyl-1,2-dioxethane, was obtained. The structures of these spiroheterocycle-containing compounds are interesting, and the reactions are potentially valuable in both organic synthesis and mechanism research.