1-(4-(tert-butyl)phenyl)cyclopropan-1-ol

• 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-(4-(tert-butyl)phenyl)cyclopropan-1-ol
• 英文别名: 1-(4-Tert-butylphenyl)cyclopropan-1-ol
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: BAIUZSIZTLUUJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(4-(tert-butyl)phenyl)cyclopropan-1-ol 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver carbonate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 0.25h， 以75%的产率得到1,6-bis(4-(tert-butyl)phenyl)hexane-1,6-dione
  参考文献：
  名称：

  Rhodium-Catalyzed Room Temperature C–C Activation of Cyclopropanol for One-Step Access to Diverse 1,6-Diketones

  摘要：

  A rhodium-catalyzed room temperature C-C activation of cyclopropanol has been demonstrated for the single-step synthesis of a range of electronically and sterically distinct 1,6-diketones. This reaction proceeds efficiently in shorter reaction time following a highly atom-economical pathway. To illustrate the synthetic potential of 1,6-diketones, aldol and macrocyclization reactions have been successfully demonstrated. Preliminary mechanistic studies revealed the involvement of nonradical pathways.

  DOI：

  10.1021/acs.orglett.0c00967
• 作为产物：
  描述：

  乙基溴化镁 在 titanium(IV) isopropylate 作用下， 以 四氢呋喃 为溶剂， 生成 1-(4-(tert-butyl)phenyl)cyclopropan-1-ol
  参考文献：
  名称：

  Rh(III)催化C-H/C-C键活化和级联环化三组分合成具有四取代碳立体中心的苯并呋喃-3(2H)-ones

  摘要：

  通过 Rh(III) 催化的 C-H/C-C 键活化和级联环化从水杨醛、环丙醇和烷基醇中一锅三组分合成具有四取代碳立构中心的苯并呋喃-3(2 H )-ones已成功开发。

  DOI：

  10.1002/adsc.202200396

文献信息

• Metal-Free Direct C-H β-Carbonyl Alkylation of Heteroarenes with Cyclopropanols Mediated by K₂ S₂ O₈
  作者：Qiang Liu、Qiang Wang、Guanqun Xie、Zeyang Fang、Shujiang Ding、Xiaoxia Wang

  DOI：10.1002/ejoc.202000289

  日期：2020.5.10

  direct C–H β‐carbonyl alkylation of heteroarenes has been achieved through K2S2O8‐mediated ring‐opening of cyclopropanols. A wide scope of substrates, such as various substituted quinolines and isoquinolines, pyridines, pyridazine, benzo[d]thiazole, and phenanthroline, underwent the β‐carbonyl alkylation efficiently and afforded the β‐heteroarylated ketones in moderate to excellent yields.

  无金属直接C-H β羰基杂芳烃烷基化已到K达到2小号2 ö 8介导的cyclopropanols的开环。各种各样的底物，例如各种取代的喹啉和异喹啉，吡啶，哒嗪，苯并[d]噻唑和菲咯啉，有效地进行了β羰基烷基化反应，并以中等至优异的产率提供了β杂芳基化的酮。
• Copper-catalysed ring-opening trifluoromethylation of cyclopropanols
  作者：Xia-Ping He、Yong-Jin Shu、Jian-Jun Dai、Wen-Man Zhang、Yi-Si Feng、Hua-Jian Xu

  DOI：10.1039/c5ob00808e

  日期：——

  A copper catalyzed ring-opening trifluoromethylation of cyclopropanols under mild reaction conditions was developed. A wide variety of synthetically useful β-trifluoromethyl ketones were obtained.

  在温和的反应条件下，开发了铜催化的环丙醇的环开放三氟甲基化反应。得到了多种合成有用的β-三氟甲基酮。
• Synthesis of chroman-4-one and indanone derivatives via silver catalyzed radical ring opening/coupling/cyclization cascade
  作者：Qiang Liu、Guanqun Xie、Qiang Wang、Zhendong Mo、Chen Li、Shujiang Ding、Xiaoxia Wang

  DOI：10.1016/j.tet.2019.130490

  日期：2019.10

  conveniently synthesized from readily available cyclopropanols and alkenyl aldehydes via a silver catalyzed radical ring-opening/coupling/cyclization cascade. The reaction proceeded under mild and neutral conditions with broad substrate scope and afforded the desired products in moderate to good yields. A probable mechanism for the cascade reaction was also proposed.

  经由银催化的自由基开环/偶联/环化级联反应，容易地从容易获得的环丙醇和烯基醛合成了多种苯并吡喃-4-酮和茚满酮衍生物。反应在温和和中性条件下，在宽范围的底物范围内进行，并以中等至良好的产率提供了所需的产物。还提出了级联反应的可能机理。
• Iron catalyzed tandem ring opening/1,6-conjugate addition of cyclopropanols with <i>p</i>-quinone methides: new access to γ,γ-diaryl ketones
  作者：Sachin R. Shirsath、Sagar M. Chandgude、M. Muthukrishnan

  DOI：10.1039/d1cc05997a

  日期：——

  An iron(III) catalyzed tandem ring opening/1,6-conjugate addition of cyclopropanols to p-quinone methides leading to γ,γ-diaryl ketones has been described. This catalytic protocol provides a novel and efficient method to access γ,γ-diaryl ketone derivatives in good to excellent yields with high functional group tolerance. Importantly, γ,γ-diaryl ketone can be further functionalized to give a versatile

  已经描述了铁（III）催化的环丙醇串联开环/1,6-共轭加成到对-醌甲基化物导致γ,γ-二芳基酮。该催化方案提供了一种新颖有效的方法，可以以良好的收率获得具有高官能团耐受性的 γ,γ-二芳基酮衍生物。重要的是，γ,γ-二芳基酮可以进一步官能化以提供一组通用的有用产品。
• Ruthenium-Catalyzed Alkylation of Cyclopropanols with Sulfoxonium Ylides via C–C Bond Cleavage: Formation of Diverse 1,5-Diketones
  作者：Mei Guan、Yong Wu、Xin Huang、Jianglian Li、Hua He、Kaichuan Yan、Ruizhi Lai、Yi Luo

  DOI：10.1055/a-1588-0974

  日期：2022.2

  A novel ruthenium-catalyzed alkylation of cyclopropanols with sulfoxonium ylides has been developed that affords diverse 1,5-diketones with good efficiency and broad substrate scope. To illustrate the synthetic applications of the obtained 1,5-diketones, aldol and cyclization reactions have been investigated. Preliminary mechanistic studies suggest that this process involves a sequential C–C activation

  已经开发了一种新型的钌催化环丙醇与 sulfoxonium 叶立德的烷基化，可提供多种 1,5-二酮，具有良好的效率和广泛的底物范围。为了说明所得 1,5-二酮的合成应用，研究了羟醛和环化反应。初步机理研究表明，该过程涉及连续的 C-C 活化和卡宾迁移插入。