9-(2-cyanoethyl)phenanthrene | 117135-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9-(2-cyanoethyl)phenanthrene
• 英文别名: 3-phenanthren-9-ylpropanenitrile
• CAS: 117135-27-0
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: VGKSCERARLSNCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  9-(2-cyanoethyl)phenanthrene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以59%的产率得到3-Phenanthren-9-yl-propylamine
  参考文献：
  名称：

  Solvent-Dependent Behavior of Phenanthrene-Amine Intramolecular Exciplexes

  摘要：

  The solvent dependence of the photophysical and photochemical behavior of several ((N,N-dimethylamino)alkyl)phenanthrenes in which the amino group is attached to the phenanthrene at C-9 or C-1 via a short polymethylene chain has been investigated. Intramolecular exciplex fluorescence is observed in moderately polar solvents but not in nonpolar solvents. The solvent dependence of exciplex fluorescence is attributed to exergonic formation of solvated exciplexes with loose geometries in polar solvents and endergonic exciplex formation in nonpolar solvents. in the case of the (aminoethyl)phenanthrene exciplex fluorescence is observed in highly polar solvents, including dimethylformamide, dimethyl sulfoxide, and acetonitrile-water binary mixtures and in frozen polar glasses. In the case of the (aminomethyl)phenanthrene moderately efficient photodeamination to yield 9-methylphenanthrene and 1,2-di-9-phenanthrylethane is observed. The solvent and temperature dependence of the kinetics of exciplex formation and decay are discussed and compared to results for other intramolecular arene-amine exciplexes.

  DOI：

  10.1021/j100092a033
• 作为产物：
  描述：

  9-phenanthrylacrylonitrile 在 sodium tetrahydroborate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 2.0h， 以65%的产率得到9-(2-cyanoethyl)phenanthrene
  参考文献：
  名称：

  Rhodes, R. Allen; Boykin, David W., Synthetic Communications, 1988, vol. 18, # 7, p. 681 - 688

  摘要：

  DOI：

文献信息

• A strategy for generating aryl radicals from arylborates through organic photoredox catalysis: photo-Meerwein type arylation of electron-deficient alkenes
  作者：Y. Iwata、Y. Tanaka、S. Kubosaki、T. Morita、Y. Yoshimi

  DOI：10.1039/c7cc09140k

  日期：——

  Photoinduced reactions of arylboronic acids with electron deficient alkenes under mild organic photoredox catalysis conditions lead to the formation of Meerwein arylation type adducts via the generation of aryl radicals.

  的温和的有机photoredox催化条件下芳基硼酸与缺电子烯烃的光诱导反应导致形成meerwein芳基化反应类型的加合物通过芳基的生成。
• 9-Cyano-10-methoxycarbonylanthracene as a Visible Organic Photoredox Catalyst in the Two-Molecule Photoredox System
  作者：Yuka Tajimi、Yasuhiro Nachi、Ryoko Inada、Ryoga Hashimoto、Mugen Yamawaki、Kei Ohkubo、Toshio Morita、Yasuharu Yoshimi

  DOI：10.1021/acs.joc.2c00643

  日期：2022.6.3

  deboronative reactions using two-molecule organic photoredox catalysts, namely, phenanthrene (Phen) and biphenyl (BP), as electron donors and 9-cyano-10-methoxycarbonylanthracene 1a as an electron acceptor were achieved. The high solubility of 1a significantly improved the reaction efficiency and product yield. In addition, the facile tuning of the oxidation potential of the electron-donor molecule via the

  使用双分子有机光氧化还原催化剂，即菲 (Phen) 和联苯 (BP) 作为电子供体和 9-cyano-10-methoxycarbonylanthracene 1a作为电子受体，实现了可见光诱导的脱羧和脱硼反应。1a的高溶解度显着提高了反应效率和产物收率。此外，通过用 BP 代替 Phen 来轻松调节电子供体分子的氧化电位，使得双分子光氧化还原系统能够应用于广泛的底物。
• Visible‐Light‐Induced Decarboxylative and Deboronative Radical Addition to Alkenes in Two‐Molecule Photoredox System Using Dibenzo[ <i>g,p</i> ]chrysene
  作者：Mugen Yamawaki、Ryoga Hashimoto、Yuki Kawabata、Miwa Ichihashi、Yasuhiro Nachi、Rinpei Inari、Chisato Sakamoto、Toshio Morita、Yasuharu Yoshimi

  DOI：10.1002/ejoc.202201225

  日期：2022.12.12

  Visible-light-induced decarboxylative and deboronative radical addition of aliphatic carboxylic acids and arylboronic acid pinacol esters to electron-deficient alkenes using two-molecule organic photoredox catalysts, such as dibenzo[g,p]chrysene and 1,4-dicyanobenzene, proceeded efficiently to furnish radical adducts via the generation of alkyl and aryl radicals.

  使用双分子有机光氧化还原催化剂，如二苯并[ g, p ] chrysene和1,4-二氰基苯，可见光诱导的脂肪族羧酸和芳基硼酸频哪醇酯对缺电子烯烃的脱羧和脱硼自由基加成反应有效进行通过产生烷基和芳基自由基来提供自由基加合物。
• RHODES, R. ALLEN;BOYKIN, DAVID W., SYNTH. COMMUN., 18,(1988) N 7, 681-687
  作者：RHODES, R. ALLEN、BOYKIN, DAVID W.

  DOI：——

  日期：——