1-[Cyclobutylidene-(4-methylphenyl)methyl]-4-methylbenzene | 128742-45-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-[Cyclobutylidene-(4-methylphenyl)methyl]-4-methylbenzene
• CAS: 128742-45-0
• 化学式: C₁₉H₂₀
• 分子量: 248.368
• InChiKey: LFFREQALISEORI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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-[Cyclobutylidene-(4-methylphenyl)methyl]-4-methylbenzene 在 Iron(III) nitrate nonahydrate 、 2,2,6,6-四甲基哌啶氧化物 作用下， 以 乙腈 为溶剂， 以80%的产率得到(1-nitrocyclobutyl)di-p-tolylmethanol
  参考文献：
  名称：

  亚烷基环丙烷和亚烷基环丁烷的氧化官能化：获得硝化环丙烷和环丁烷的多功能平台

  摘要：

  Fe(NO 3 ) 3 ·9H 2 O 或 AgNO 2对亚烷基环丙烷 (ACPs) 和亚烷基环丁烷 (ACBs) 进行了不同的自由基硝化反应，得到 β-硝基醇、α-硝基酮和硝基亚硝化三类产品产率高达 90% 的产品。特别是，环丙基和环丁基环在产物中是保守的。通过放大实验和将硝基还原为氨基，证明了该方法的适用性。初步的机理研究表明，硝基自由基参与了反应过程。

  DOI：

  10.1039/d2ob01426b
• 作为产物：
  描述：

  2,2-Bis(4-methylphenyl)spiro[2.2]pentane 在 蒽醌 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以19%的产率得到1-[Cyclobutylidene-(4-methylphenyl)methyl]-4-methylbenzene
  参考文献：
  名称：

  Divergent rearrangement pathways in the electron-transfer induced spiropentane-methylenecyclobutane rearrangement: Role of cip and ssip

  摘要：

  DOI：

  10.1016/s0040-4039(00)97375-1

文献信息

• Reactions of methylenecyclobutanes with silver acetate and iodine
  作者：Min Jiang、Le-Ping Liu、Min Shi

  DOI：10.1016/j.tet.2007.07.046

  日期：2007.9

  Methylenecyclobutanes undergo an interesting rearrangement reaction in the presence of silver acetate and iodine at room temperature (20 °C) in dichloromethane to give the corresponding aryl-(1-arylcyclobutyl)methanones in good to high yields within short reaction time. A plausible reaction mechanism has been discussed on the basis of control and O18-labeling experiments.

  亚甲基环丁烷在乙酸银和碘的存在下于室温（20°C）的二氯甲烷中进行有趣的重排反应，从而在较短的反应时间内以高至高收率得到相应的芳基-（1-芳基环丁基）亚甲基酮。已经在对照和O 18标记实验的基础上讨论了合理的反应机理。
• Fluorination of alkylidenecyclopropanes and alkylidenecyclobutanes: divergent synthesis of fluorinated cyclopropanes and cyclobutanes
  作者：Jin-Bo Wu、Shuang Li、Shuai Han、Yue Wang、Wei Zhang、Zhen Wang、Yao-Fu Zeng

  DOI：10.1039/d3ob00785e

  日期：——

  A divergent fluorination of alkylidenecyclopropanes (ACPs) and alkylidenecyclobutanes (ACBs) with selectfluor has been achieved. Four different types of products including fluorohydrins, fluoroethers, fluoroesters and fluoroketones could be prepared in moderate to excellent yields. In particular, the cyclopropanes and cyclobutanes were not destroyed during the transformations which involved a radical

  亚烷基环丙烷 (ACP) 和亚烷基环丁烷 (ACB) 与 selectflu 的不同氟化反应已经实现。可以以中等至优异的产率制备四种不同类型的产品，包括氟代醇、氟代醚、氟代酯和氟代酮。特别是，环丙烷和环丁烷在涉及自由基途径的转化过程中没有被破坏。通过产品的各种转化证明了该方法的适用性。
• Acetoxylation and Hydroxylation of Diarylmethylenecycloalkanes via Radical Approach
  作者：Min Jiang、Yin Wei、Min Shi

  DOI：10.1021/jo9027209

  日期：2010.4.16

  Diarylmethylenecycloalkanes were acetoxylated under the radical reaction conditions with PhI(OAc)(2), I-2, and TsNH2. Moreover, upon treating the products from the reactions of methylenecyclobutanes with N-bromosuccinimide (NBS) through silica gel column chromatography, the corresponding substituted methylenecyclobutanols were obtained in moderate to good yields. The plausible mechanisms have been proposed on the basis of the control experiments.
• Aluminum Chloride-Mediated Acylation of Methylenecyclobutanes. A Facile Synthetic Protocol for the Construction of Substituted Cyclopentenes
  作者：Min Jiang、Min Shi

  DOI：10.1021/ol8006502

  日期：2008.6.5

  Reactions of methylenecyclobutanes (MCBs) with acyl chlorides produce the corresponding substituted cyclopentene derivatives in moderate to high yields via ring enlargement in the presence of aluminum chloride under mild conditions. A plausible mechanism has been proposed on the basis of control and deuterium labeling experiments.