α-<4-Fluor-phenyl>-zimtsaeure-nitril | 2558-28-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: α-<4-Fluor-phenyl>-zimtsaeure-nitril
• 英文别名: 4-Fluor-α-cyan-stilben；2-(4-fluorophenyl)-3-phenylprop-2-enenitrile
• CAS: 2558-28-3
• 化学式: C₁₅H₁₀FN
• 分子量: 223.25
• InChiKey: AWMKCXLADSGTQN-UHFFFAOYSA-N

物化性质

• 熔点：
  101-105 °C(lit.)
• 沸点：
  333.1±30.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下稳定，应避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  α-<4-Fluor-phenyl>-zimtsaeure-nitril 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 2-(4-fluorophenyl)-3-phenylpropanenitrile
  参考文献：
  名称：

  Heteroaryl β-tetralin ureas as novel antagonists of human TRPV1

  摘要：

  We report on a series of alpha-substituted-beta-tetralin-derived and related phenethyl-based isoquinolinyl and hydroxynaphthyl ureas as potent antagonists of the human TRPV1 receptor. The synthesis and Structure-activity relationships (SAR) of the series are described. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.036
• 作为产物：
  描述：

  对氟甲苯 在 sodium ethanolate 、 氯 作用下， 以 乙醇 为溶剂， 生成 α-<4-Fluor-phenyl>-zimtsaeure-nitril
  参考文献：
  名称：

  Jerumanis,S.; Bruylants,A., Bulletin des Societes Chimiques Belges, 1960, vol. 69, p. 312 - 322

  摘要：

  DOI：

文献信息

• Switchable Cobalt-Catalyzed α-Olefination and α-Alkylation of Nitriles with Primary Alcohols
  作者：Keshav Paudel、Shi Xu、Keying Ding

  DOI：10.1021/acs.orglett.1c01553

  日期：2021.7.2

  The first switchable α-olefination and α-alkylation of nitriles with primary alcohols catalyzed by a well-defined base transition-metal Co complex was presented. A broad variety of nitriles and primary alcohols are selectively and efficiently converted to the corresponding products by this method. It is noteworthy that the transformation is environmentally benign and atom efficient with H2 and H2O

  首次提出了在明确的碱性过渡金属 Co 配合物催化下，腈与伯醇的可切换 α-烯化和 α-烷基化。通过这种方法，多种腈和伯醇被选择性地、高效地转化为相应的产物。值得注意的是，该转化对环境无害且原子效率高，H 2和 H 2 O 是唯一的副产物。
• Dialkylamino cyclopentadienyl ruthenium(<scp>ii</scp>) complex-catalyzed α-alkylation of arylacetonitriles with primary alcohols
  作者：Hung Wai Cheung、Juan Li、Wenxu Zheng、Zhongyuan Zhou、Yu Hin Chiu、Zhenyang Lin、Chak Po Lau

  DOI：10.1039/b917805h

  日期：——

  Aminocyclopentadienyl ruthenium complexes, [(η5-C5H4NMe2)Ru(PPh3)2(CH3CN)]+BF4− and [(η5-C5H4NEt2)Ru(PPh3)2(CH3CN)]+BF4−, are moderately active catalysts for α-alkylation of arylacetonitriles with primary alcohols; on the other hand, the analogous unsubstituted cyclopentadienyl ruthenium complex [(η5-C5H5)Ru(PPh3)2(CH3CN)]+BF4− shows very low catalytic activity. On the basis of experimental results and theoretical calculations, rationalization for the much higher catalytic activity of the aminocyclopentadienyl complexes over that of the unsubstituted Cp complex is provided. In the catalytic systems with the former, it is possible to regenerate the active solvento complexes via protonation of the metal hydride intermediates and subsequent ligand substitution; this process is, however, very nonfacile in the catalytic system with the latter.

  氨基环戊二烯基钌配合物 [(η⁵-C₅H₄NMe₂)Ru(PPh₃)₂(CH₃CN)]⁺BF₄⁻ 和 [(η⁵-C₅H₄NEt₂)Ru(PPh₃)₂(CH₃CN)]⁺BF₄⁻ 是对芳基乙腈与初级醇的α-烷基化反应具有适度活性的催化剂；另一方面，类似的未取代环戊二烯基钌配合物 [(η⁵-C₅H₅)Ru(PPh₃)₂(CH₃CN)]⁺BF₄⁻ 显示出非常低的催化活性。根据实验结果和理论计算，对氨基环戊二烯基配合物相较于未取代Cp配合物的催化活性显著更高的原因进行了合理解释。在采用前者的催化体系中，可以通过金属氢化物中间体的质子化和随后的配体置换来再生活性溶剂配合物；然而，在后者的催化体系中，这一过程则非常不易。
• Chemoselective α-Alkylation and α-Olefination of Arylacetonitriles with Alcohols <i>via</i> Iron-Catalyzed Borrowing Hydrogen and Dehydrogenative Coupling
  作者：Ramachandra Reddy Putta、Simin Chun、Seok Beom Lee、Junhwa Hong、Seung Hyun Choi、Dong-Chan Oh、Suckchang Hong

  DOI：10.1021/acs.joc.2c02050

  日期：2022.12.16

  borrowing hydrogen or α-olefination by dehydrogenative coupling methods. Designing and developing high-performance earth-abundant catalysts that can procure different products from the same starting materials remain a great challenge. Herein, we report an iron(0) catalyst system that achieves chemoselectivity between borrowing hydrogen and dehydrogenative coupling protocols by simply changing the base. A

  α-烷基腈和α-烯烃腈在有机合成和药物化学中非常重要。然而，不同类型的催化剂用于通过借氢实现腈的α-烷基化或通过脱氢偶联方法实现α-烯烃化。设计和开发高性能的地球丰富的催化剂，可以从相同的起始材料中获得不同的产品仍然是一个巨大的挑战。在此，我们报告了一种铁 (0) 催化剂系统，该系统通过简单地改变碱基来实现借氢和脱氢偶联方案之间的化学选择性。广泛的腈类和醇类，包括苄醇、直链脂肪醇、脂环醇、杂环醇和烯丙醇，被选择性且有效地转化为相应的产物。机理研究表明反应机理通过脱氢途径进行。这种铁催化方案对环境无害且原子效率高，可释放 H2和 H 2 O 作为绿色副产物。
• Transition-Metal-Free and Selective Deconstructive Carbonyl Olefination of α-Hydroxy Ketones: A Complementary Approach to Knoevenagel Reaction
  作者：Anil Kumar、Sandeep Sandeep、Vaneet Saini、Chayawan Chayawan、Ganga R. Chaudhary、Paloth Venugopalan

  DOI：10.1055/a-2114-7802

  日期：2023.10

  While the carbonyl olefination has been extensively studied and well documented, use of α-hydroxy ketones as precursors for the carbonyl olefination is not reported, till date. Herein, a transition-metal-free and selective Knoevenagel-type deconstructive carbonyl olefination of α-hydroxy ketones using arylacetonitriles under mild reaction conditions is presented. The reaction affords valuable scaffolds

  虽然羰基烯化已被广泛研究并有充分记录，但迄今为止，尚未报道使用 α-羟基酮作为羰基烯化的前体。在此，提出了在温和反应条件下使用芳基乙腈进行 α-羟基酮的无过渡金属且选择性 Knoevenagel 型解构羰基烯化。该反应使用 α-羟基酮作为羰基烯化的前体，提供了有价值的丙烯腈支架。
• Heteroaryl β-tetralin ureas as novel antagonists of human TRPV1
  作者：Michele C. Jetter、Mark A. Youngman、James J. McNally、Mark E. McDonnell、Sui-Po Zhang、Adrienne E. Dubin、Nadia Nasser、Ellen E. Codd、Christopher M. Flores、Scott L. Dax

  DOI：10.1016/j.bmcl.2007.09.036

  日期：2007.11

  We report on a series of alpha-substituted-beta-tetralin-derived and related phenethyl-based isoquinolinyl and hydroxynaphthyl ureas as potent antagonists of the human TRPV1 receptor. The synthesis and Structure-activity relationships (SAR) of the series are described. (C) 2007 Elsevier Ltd. All rights reserved.