4-(4-fluorophenyl)-4-oxo-2-phenylbutanenitrile | 581-01-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-(4-fluorophenyl)-4-oxo-2-phenylbutanenitrile
• 英文别名: 4-(4-fluoro-phenyl)-4-oxo-2-phenyl-butyronitrile；4-(4-Fluor-phenyl)-4-oxo-2-phenyl-butyronitril；(+/-)-4-Oxo-2-phenyl-4-(4-fluor-phenyl)-buttersaeure-nitril；4-Fluoro-I(3)-oxo-I+/--phenylbenzenebutanenitrile
• CAS: 581-01-1
• 化学式: C₁₆H₁₂FNO
• 分子量: 253.276
• InChiKey: PLIRVWZEEWVMGG-UHFFFAOYSA-N

物化性质

• 沸点：
  436.6±40.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)
• 熔点：
  102 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-4-oxo-2-phenylbutanenitrile 生成 methyl 4-(4-fluorophenyl)-4-oxo-2-phenylbutanoate
  参考文献：
  名称：

  Allen; Normington; Wilson, Canadian Journal of Research, 1934, vol. 11, p. 386

  摘要：

  DOI：
• 作为产物：
  描述：

  氰化钾 、 alkaline earth salt of/the/ methylsulfuric acid 生成 4-(4-fluorophenyl)-4-oxo-2-phenylbutanenitrile
  参考文献：
  名称：

  Allen; Normington; Wilson, Canadian Journal of Research, 1934, vol. 11, p. 386

  摘要：

  DOI：

文献信息

• Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone
  作者：Zhao-Feng Li、Qian Li、Li-Qing Ren、Qing-Hua Li、Yun-Gui Peng、Tang-Lin Liu

  DOI：10.1039/c9sc00640k

  日期：——

  nickel-catalyzed, high atom- and step-economical reaction of cyanohydrins with aldehydes or ketones via an unprecedented “cyano-borrowing reaction” has been developed. Cleavage of the C–CN bond of cyanohydrins followed by aldol condensation and conjugate addition of cyanide to α,β-unsaturated ketones proceeded to deliver a range of racemic β-cyano ketones with good to high yields. The practical procedure

  通过前所未有的“借氰反应” ，氰醇与醛或酮的直接镍催化、高原子和多步经济的反应已被开发出来。氰醇的 C-CN 键断裂，然后是羟醛缩合和氰化物与 α,β-不饱和酮的共轭加成，以良好至高产率提供一系列外消旋 β-氰基酮。使用商业和毒性较低的 CN 源的实际程序预示着该协议的广泛应用。
• Scalable Electrocatalytic Intermolecular Acylcyanation and Aminocyanation of Alkenes
  作者：Xianqiang Kong、Xiaohui Chen、Yiyi Chen、Zhong-Yan Cao

  DOI：10.1021/acs.joc.1c03134

  日期：2022.6.3

  Electrocatalytic three-component acylcyanation and aminocyanation of simple alkenes have been developed. The protocol features high functional group tolerance and can easily be scaled up. The key to success is to use an electrophilic cyanation source, enabling a broadened use of alkenes to aliphatic ones for acylcyanation.

  已经开发了简单烯烃的电催化三组分酰氰化和氨基氰化。该协议具有高功能组耐受性，可以轻松扩展。成功的关键是使用亲电氰化源，使烯烃的使用范围扩大到脂肪族的酰基氰化。
• An efficient conjugate hydrocyanation of chalcones and related enones with TMSCN under solvent- and additive-free microwave conditions
  作者：Hirokazu Iida、Tatsuya Moromizato、Hiroshi Hamana、Kiyoshi Matsumoto

  DOI：10.1016/j.tetlet.2006.12.145

  日期：2007.3

  A first example of solvent- and additive-free 1,4-addition reaction of alpha,beta-unsaturated ketones such as chalcones, 3-nonen-2-one and benzalacetone with trimethylsilyl cyanide (TMSCN) is described. The addition of TMSCN to chalcones, 3-nonen-2-one, and benzalacetone under microwave irradiation in the absence of Lewis or Bronsted acids and solvents, yielded the corresponding beta-cyanoketones in good to moderate yields, as quite rapidly as in 5 min. No systematic substituent effect of chalcones on the yields was observed. No reaction of alpha,beta-unsaturated esters such as methyl cinnamate with TMSCN took place under the same conditions. (c) 2007 Published by Elsevier Ltd.
• Coudert, P.; Couquelet, J.; Tronche, P., Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 799 - 802
  作者：Coudert, P.、Couquelet, J.、Tronche, P.

  DOI：——

  日期：——
• COUDERT, P.;COUQUELET, J.;TRONCHE, P., J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 799-802
  作者：COUDERT, P.、COUQUELET, J.、TRONCHE, P.

  DOI：——

  日期：——