3-(4-叔丁基苯基)丙腈 | 69300-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(4-叔丁基苯基)丙腈
• 英文名称: 3-(4-(tert-butyl)phenyl)propanenitrile
• 英文别名: 3-(4-Tert-butylphenyl)propanenitrile
• CAS: 69300-16-9
• 化学式: C₁₃H₁₇N
• 分子量: 187.285
• InChiKey: YBASOBYKVCNWTN-UHFFFAOYSA-N

物化性质

• 沸点：
  308.3±11.0 °C(Predicted)
• 密度：
  0.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-叔丁基苯基)丙腈 在 硼烷四氢呋喃络合物 作用下， 生成 4-叔丁基苯丙胺
  参考文献：
  名称：

  Guanidinium and amidinium fungicides: A new class of carbocation mimetic ergosterol biosynthesis inhibitors

  摘要：

  AbstractA novel class of chemical has been designed with the aim of inhibiting the Δ14‐reductase and Δ8‐Δ7‐isomerase enzymes in the ergosterol biosynthesis pathway in fungi. Use was made of knowledge about the mechanisms of both enzymes and the mode of action of known, fungicidal inhibitors of these enzymes. Pioneer examples have been synthesised and have been demonstrated to be potent inhibitors of ergosterol biosynthesis in Ustilago maydis (DC) Corda, acting in the same manner as the commercial fungicide fenpropimorph. They also showed excellent fungicidal activity against Erysiphe graminis DC f. sp. hordei Marchal (powdery mildew of barley) and Puccinia recondita Rob. ex Desm. (wheat leaf rust) in in‐vivo glasshouse tests. Using these compounds as a starting point, systematic structural variation has been carried out. Testing of a wide range of analogues at high volume confirms the potential of this class of compound to control mildew and rust pathogens at levels comparable to those of the standards. Correlation of in‐vivo and enzymatic data is good and the structure‐activity relationship developed for this series of compounds closely parallels that found for the morpholine/piperidine class of fungicides, suggesting a common mode of action.

  DOI：

  10.1002/ps.2780440406
• 作为产物：
  描述：

  3-(4-(tert-butyl)phenyl)acrylonitrile 在 乙醇 、 [iridium bis(2-(2,4-difluorophenyl)pyridinate) (9,10-phenanthroline)]hexafluorophosphate 、 三对苯甲基膦 作用下， 以76 %的产率得到3-(4-叔丁基苯基)丙腈
  参考文献：
  名称：

  磷自由基使炔烃发生光致发散氰化

  摘要：

  描述了由磷自由基​​启用的光化学诱导的炔烃选择性和发散氰化反应。使用简单的三芳基膦作为助催化剂，可以发散地实现包括二氢氰化、反马尔可夫尼科夫氢氰化和多米诺氢氰化/还原在内的三种氰化反应，提供范围广泛的烷基二腈、烯基腈和烷基温和条件下的腈类。

  DOI：

  10.1002/anie.202210838

文献信息

• Cob(I)alamin als Katalysator. 1. Mitteilung. Reduktion von gesättigten Nitrilen in wässeriger Lösung
  作者：Albert Fischli

  DOI：10.1002/hlca.19780610727

  日期：1978.11.1

  Co(I)alamin as Catalyst. 1. Communication. Reduction of Saturated Nitriles in Aqueous Solution

  Co（I）阿拉明作为催化剂。1.沟通。还原水溶液中的饱和腈
• Overcoming Selectivity Issues in Reversible Catalysis: A Transfer Hydrocyanation Exhibiting High Kinetic Control
  作者：Benjamin N. Bhawal、Julia C. Reisenbauer、Christian Ehinger、Bill Morandi

  DOI：10.1021/jacs.0c03184

  日期：2020.6.24

  Reversible catalytic reactions operate under thermodynamic control and thus establishing a selective catalytic system poses a considerable challenge. Herein, we report a reversible transfer hydrocyanation protocol that exhibits high selectivity for the thermodynamically less favorable branched isomer. Selectivity is achieved by exploiting the lower barrier for C-CN oxidative addition and reductive elimination

  可逆催化反应在热力学控制下运行，因此建立选择性催化体系提出了相当大的挑战。在此，我们报告了一种可逆转移氢氰化方案，该方案对热力学不太有利的支化异构体表现出高选择性。在不存在共催化路易斯酸的情况下，通过在苄基位置利用 C-CN 氧化加成和还原消除的较低势垒来实现选择性。通过设计一种新型的 HCN 供体，实现了一种实用的、支链选择性的、无 HCN 的转移氢氰化反应。支链和线性腈异构体混合物的合成有用拆分也被证明强调了可逆和选择性转移反应的价值。在更广泛的背景下，
• Visible- and UV-Light-Induced Decarboxylative Radical Reactions of Benzoic Acids Using Organic Photoredox Catalysts
  作者：Suzuka Kubosaki、Haruka Takeuchi、Yutaka Iwata、Yosuke Tanaka、Kazuyuki Osaka、Mugen Yamawaki、Toshio Morita、Yasuharu Yoshimi

  DOI：10.1021/acs.joc.0c00055

  日期：2020.4.17

  reactions of benzoic acids with electron-deficient alkenes, diborane, and acetonitrile under organic photoredox catalysis conditions and mild heating afforded adducts, arylboronate esters, and the reduction product, respectively. The reaction is thought to involve single-electron transfer promoted the generation of aryl radicals via decarboxylation. A diverse range of benzoic acids were found to be suitable

  在有机光氧化还原催化条件下和温和加热下，苯甲酸与缺电子的烯烃，乙硼烷和乙腈进行光诱导的脱羧自由基反应，分别得到加合物，芳基硼酸酯和还原产物。该反应被认为涉及单电子转移，该反应通过脱羧促进了芳基的产生。发现多种苯甲酸是用于该光反应的合适的底物。只有我们的两分子有机光氧化还原系统才能很好地实现苯甲酸的直接光诱导脱羧。
• 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。
• Iridium-catalyzed α-Alkylation of Acetonitrile with Primary and Secondary Alcohols
  作者：Takuya Sawaguchi、Yasushi Obora

  DOI：10.1246/cl.2011.1055

  日期：2011.9.5

  Acetonitrile is successfully alkylated with primary and secondary alcohols in the presence of t-BuOK using [Ir(OH)(cod)]2 as a catalyst. This method provides a very clean and atom-economical convenient direct route to substituted nitriles, which are very important raw materials in organic and industrial chemistry.

  使用 [Ir(OH)(cod)]2 作为催化剂，在存在 t-BuOK 的情况下，乙腈成功地与一元和二元醇进行烷基化。这种方法提供了一条非常干净和原子经济的直接途径，得到的取代腈是有机化学和工业化学中非常重要的原料。