2-(4-bromophenyl)-4-oxo-4-phenylbutanenitrile

• 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: 2-(4-bromophenyl)-4-oxo-4-phenylbutanenitrile
• 英文别名: 2-(4-Bromophenyl)-4-oxo-4-phenylbutanenitrile
• 化学式: C₁₆H₁₂BrNO
• 分子量: 314.181
• InChiKey: WBWDSMBURXJHKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)-4-oxo-4-phenylbutanenitrile 在 potassium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 2.0h， 以59%的产率得到3-(4-bromophenyl)-5-hydroxy-5-phenyl-1,5-dihydro-2H-pyrrol-2-one
  参考文献：
  名称：

  通过碱辅助3-氰酮环化制备3,5-二芳基取代的5-羟基-1,5-二氢-2H-吡咯-2-酮

  摘要：

  开发了一种方便的制备方法，允许从常规可用的廉价合成前体快速组装 3,5-二芳基取代的 5-羟基-1,5-二氢-2H-吡咯-2-酮。这些化合物无法通过先前已知的方案制备，而是生产 2-氨基呋喃衍生物。

  DOI：

  10.1039/d1ra02279b
• 作为产物：
  描述：

  2-hydroxy-2-phenylpropionitrile 、 对溴苯甲醛 在 nickel dichloride 、 lithium hydroxide 、 正丁基二(1-金刚烷基)膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.5h， 以73%的产率得到2-(4-bromophenyl)-4-oxo-4-phenylbutanenitrile
  参考文献：
  名称：

  借氰反应：镍催化的氰醇和醛/酮直接转化为 β-氰基酮†

  摘要：

  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。

  DOI：

  10.1039/c9sc00640k

文献信息

• Cyanation of α,β-unsaturated enones by malononitrile in open air under metal-catalyst-free conditions
  作者：Shaoxia Lin、Ying Wei、Fushun Liang

  DOI：10.1039/c2cc35528k

  日期：——

  Cyanation of α,β-unsaturated enones by employing malononitrile as the organic cyanation source has been disclosed, which proceeds efficiently at room temperature in open air under metal-catalyst-free conditions.

  已经披露了通过使用氢氰酸腈作为有机氰化源对α,β-不饱和酮进行氰化反应，该反应在常温下在开放空气中，以无金属催化剂的条件高效进行。
• 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。
• Electrocatalytic Hydrogen Evolution Reaction Enabling Cyanation of Electron‐poor Carbons with Acetone Cyanohydrin
  作者：Valerio Morlacci、Caterina Momoli、Meklind Ndrita、Massimiliano Aschi、Antonio Arcadi、Laura Palombi

  DOI：10.1002/ejoc.202400236

  日期：2024.6.10

  Herein is reported an electrochemical procedure based on the Hydrogen Evolution Reaction of acetone cyanohydrin at a Pt cathode enabling the cyanation of α,β- unsaturated carbonyl and imines. Catalytic current, along with a correspondingly reduced quantity of supporting electrolyte, facilitates the scalability of the procedure, ensuring brief electrolysis times while maintaining a simple electrochemical

  本文报道了一种基于丙酮氰醇在 Pt 阴极上的析氢反应的电化学过程，能够实现 α,β-不饱和羰基和亚胺的氰化。催化电流以及相应减少的支持电解质数量，促进了该过程的可扩展性，确保短暂的电解时间，同时保持简单的电化学设计。
• 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.
• Thiourea-functionalized magnetic hydroxyapatite as a recyclable inorganic–organic hybrid nanocatalyst for conjugate hydrocyanation of chalcones with TMSCN
  作者：Afsaneh Arefi Oskouie、Salman Taheri、Leila Mamani、Akbar Heydari

  DOI：10.1016/j.catcom.2015.08.016

  日期：2015.12

  The recoverable nanomagnetic catalyst was manufactured based on thiourea modified magnetic hydroxyapatite. Magnetic hydroxyapatite (mHAp) as the inorganic-organic hybrid support was fabricated using co-precipitate condition and then modified via the covalently anchoring of 1-(3,5-bis(trifluoromethyl)phenyl-3-propyl)thiourea. The hybrid nano-catalyst has been identified by TEM, SEM, FTIR, BET, TGA, and XRD. This nanocatalyst appeared efficient and robust in the 1,4-addition reaction of TMSCN to alpha,beta-unsaturated aromatic enones in excellent yields (85-96%) under mild reaction condition and simple work-up process. This recoverable organocatalyst has a great potential as an industrially viable and eco-safe catalyst. (C) 2015 Elsevier B.V. All rights reserved.