9-环丙基蒽 | 26979-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 9-环丙基蒽
• 英文名称: 9-cyclopropylanthracene
• CAS: 26979-34-0
• 化学式: C₁₇H₁₄
• 分子量: 218.298
• InChiKey: YRPJEFPAWJPKAX-UHFFFAOYSA-N

物化性质

• 沸点：
  399.3±9.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  9-环丙基蒽 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 9-(α-Bromocyclopropyl)anthracene
  参考文献：
  名称：

  Kinetic vs. thermodynamic factors in .alpha.-hydrogen atom abstractions from alkyl aromatics

  摘要：

  DOI：

  10.1021/jo00304a029
• 作为产物：
  描述：

  溴代环丙烷 、 蒽酮 在 碘 、 magnesium 作用下， 生成 9-环丙基蒽
  参考文献：
  名称：

  Kinetic vs. thermodynamic factors in .alpha.-hydrogen atom abstractions from alkyl aromatics

  摘要：

  DOI：

  10.1021/jo00304a029

文献信息

• Palladium-catalysed direct cross-coupling of secondary alkyllithium reagents
  作者：Carlos Vila、Massimo Giannerini、Valentín Hornillos、Martín Fañanás-Mastral、Ben L. Feringa

  DOI：10.1039/c3sc53047g

  日期：——

  Palladium-catalysed cross-coupling of secondary C(sp3) organometallic reagents has been a long-standing challenge in organic synthesis, due to the problems associated with undesired isomerisation or the formation of reduction products. Based on our recently developed catalytic C–C bond formation with organolithium reagents, herein we present a Pd-catalysed cross-coupling of secondary alkyllithium reagents with aryl and alkenyl bromides. The reaction proceeds at room temperature and on short timescales with high selectivity and yields. This methodology is also applicable to hindered aryl bromides, which are a major challenge in the field of metal catalysed cross-coupling reactions.

  钯催化的二级C(sp3)有机金属试剂交叉偶联反应一直是有机合成中的一个长期挑战，主要由于与不期望的异构化或还原产物形成相关的问题。基于我们最近开发的与有机锂试剂的催化C–C键形成反应，本文呈现了一种钯催化的二级烷基锂试剂与芳基和烯基溴化物的交叉偶联反应。该反应在室温下进行，反应时间短，选择性和产率均很高。这一方法也适用于受阻的芳基溴化物，而这在金属催化的交叉偶联反应中是一个主要挑战。
• Radical Ion Probes. 9. The Chemistry of Radical Cations Derived from 9-Cyclopropylanthracene and 9-Bromo-10-cyclopropylanthracene
  作者：Yonghui Wang、Karen H. McLean、J. M. Tanko

  DOI：10.1021/jo971524t

  日期：1998.2.1

  Reactions of radical cations generated from 9-cyclopropylanthracene (1) and 9-bromo-10-cyclopropylanthracene (2) in the presence of methanol have been investigated electrochemically. The major products arising from oxidation of both substrates are attributable to CH(3)OH attack at the aromatic ring (occurring at the radical cation stage for 2 and the dication stage for 1) rather than CH(3)OH-induced

  电化学研究了由9-环丙基蒽（1）和9-溴-10-环丙基蒽（2）在甲醇存在下生成的自由基阳离子的反应。两种底物氧化产生的主要产物归因于芳香环上的CH（3）OH攻击（发生在自由基阳离子阶段为2和离子化阶段为1），而不是CH（3）OH诱导的环丙烷开环，估计放热为20 kcal / mol。尽管在某些情况下检测到开环产物，但发现它们是由初级氧化产物的后续反应引起的。
• Direct Suzuki‐Miyaura Coupling of Naphthalene‐1,8‐diaminato (dan)‐Substituted Cyclopropylboron Compounds
  作者：Mikinao Koishi、Kazuki Tomota、Masaaki Nakamoto、Hiroto Yoshida

  DOI：10.1002/adsc.202201141

  日期：2023.3.7

  describe the direct Suzuki-Miyaura coupling of dan-substituted, saturated organoboron compounds. Despite its Lewis acidity-diminished character of the boron center, cyclopropyl-B(dan) can be activated by t-BuOK to undergo transmetalation with a palladium complex. The increased s-character of the C−B(dan) bond as compared with other alkyl-B(dan) should be the key to the reaction.

  我们在此描述了丹取代的饱和有机硼化合物的直接 Suzuki-Miyaura 偶联。尽管硼中心具有路易斯酸度降低的特性，但环丙基-B(dan) 可以被t -BuOK 激活，与钯配合物进行金属转移。与其他烷基-B(dan)相比，C−B(dan)键的s-特征增加应该是反应的关键。
• Conformational analysis of cyclopropyl groups attached to trigonal carbon in organic radicals
  作者：Nathan L. Bauld、John D. McDermed、Charles E. Hudson、Yong S. Rim、Jerome Zoeller、Ronnie Drew Gordon、James S. Hyde

  DOI：10.1021/ja01052a023

  日期：1969.11
• Kinetic vs. thermodynamic factors in .alpha.-hydrogen atom abstractions from alkylaromatics. 2. Reactivities of .alpha.-alkylnaphthalenes and several conformationally locked alkylaromatics toward bromine atom
  作者：James M. Tanko、N. Kamrudin、Joseph F. Blackert

  DOI：10.1021/jo00022a034

  日期：1991.10

  The relative reactivities of alpha-methyl-, alpha-ethyl-, and alpha-isopropylnaphthalene toward bromine atom have been determined. A partial breakdown in the normal reactivity pattern (tertiary > secondary > primary) is observed: CH3 (1.00) < CH2CH3 (5.7) > CH(CH3)2 (4.7) per hydrogen at 80-degrees-C. These data (in conjunction with earlier results for the phenyl and 9-anthryl series) show that for alkylaromatics in general, the anticipated correlation between log (k(rel)) and DELTA-H-degree for alpha-hydrogen abstractions by bromine atom is poor. This breakdown in the Evans and Polanyi (E&P) relationship and the observed selectivity reversals in the alpha-naphthyl and 9-anthryl series are attributed to stereoelectronic factors, specifically the alignment of the alpha-C-H bond with the adjacent pi-system in the starting alkylaromatic. The reactivities of indane, 1,8-ethylenenaphthalene, and 1,9-ethyleneanthracene (relative to the corresponding ethylarenes) provide further evidence for the role of stereoelectronic factors. These stereoelectronic factors are reconciled with the E&P equation quantitatively: An excellent correlation between log k(rel) and (sin2 theta x DELTA-H-degree is observed (where theta is the angle defined by the alpha-C-H bond with respect to the aromatic plane). The basis for this treatment and its relationship to the E&P equation is discussed.