4,4-dimethyl-3-oxo-2-[1-phenylmeth-(E)-ylidene]pentanenitrile | 1189116-34-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4,4-dimethyl-3-oxo-2-[1-phenylmeth-(E)-ylidene]pentanenitrile
• 英文别名: (E)-2-benzylidene-4,4-dimethyl-3-oxo-pentanenitrile；2-benzylidene-4,4-dimethyl-3-oxopentanenitrile；(2E)-2-benzylidene-4,4-dimethyl-3-oxopentanenitrile
• CAS: 1189116-34-4
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: LCWFGOJVGVBWLE-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  4,4-dimethyl-3-oxo-2-[1-phenylmeth-(E)-ylidene]pentanenitrile 、 2,3-二甲基-1,3-丁二烯 在 三氯化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以80%的产率得到3,4-dimethyl-6-phenyl-1-pivaloylcyclohex-3-ene-1-carbonitrile
  参考文献：
  名称：

  Diels–Alder reactions of acyclic α-cyano α,β-alkenones: a new approach to highly substituted cyclohexene system

  摘要：

  The Diels-Alder reactions of a variety of acyclic a-cyano a,p-unsaturated ketones 8 have been investigated. With the assistance of boron trichloride, these compounds were found to undergo the cycloaddition readily with dienes to give the corresponding adducts 9 in good to high yields. In addition, some of 9 could be further subjected to the reductive alkylation reactions using lithium naphthalenide (LN) and an appropriate alkylating agent, thus allowing for the generation of highly substituted cyclohexenes 10 with the replacement of the cyano group with an alkyl substituent. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.105
• 作为产物：
  描述：

  2-benzyl-4,4-dimethyl-3-oxopentanenitrile 在 2-碘酰基苯甲酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 2.0h， 以72%的产率得到4,4-dimethyl-3-oxo-2-[1-phenylmeth-(E)-ylidene]pentanenitrile
  参考文献：
  名称：

  IBX 介导的取代 β-氧腈的脱氢反应

  摘要：

  介绍了一种用于 β-氧腈温和脱氢的简便方法。当用邻碘苯甲酸 (IBX) 处理时，这些化合物中的一系列被转化为它们的不饱和对应物。此外，我们表明脱氢产物可以原位反应，与烯醇醚发生快速的杂狄尔斯-阿尔德反应，得到多取代的二氢吡喃。我们还描述了环状 β-氧腈的脱氢，这导致了取代酚的形成。

  DOI：

  10.1002/ejoc.201402007

文献信息

• Fluorous bispidine: a bifunctional reagent for copper-catalyzed oxidation and knoevenagel condensation reactions in water
  作者：Wei Jie Ang、Yong Sheng Chng、Yulin Lam

  DOI：10.1039/c5ra17093a

  日期：——

  Fluorous bispidine-type ligands have been developed to demonstrate its bifunctional property as a ligand and base in copper-catalyzed aerobic oxidation, the Knoevenagel condensation and tandem oxidation/condensation in water under mild conditions.

  氟亲和性双咪唑型配体已被开发用于展示其在铜催化的氧化反应、Knoevenagel缩合和水中温和条件下串联氧化/缩合反应中作为配体和碱的双功能性质。
• Phosphine-Catalyzed Reaction of Cyanohydrins with Activated Alkynes
  作者：Olivier Loreau、Frédéric Taran、Acétou Siby

  DOI：10.1055/s-0029-1216827

  日期：2009.7

  new method for preparing α-cyanoacrylates and α-cyanoenones is described. The procedure uses a phosphine-catalyzed α-C addition of cyanide ion, generated in situ from cyanohydrins, to activated alkynes. An unexpected tandem reaction producing benzylidenecyclopentanones is also described. cyanoacrylates - alkynes - catalysis - phosphines

  描述了一种制备α-氰基丙烯酸酯和α-氰基烯酮的新方法。该方法使用了由膦醇催化的氰基离子的α-C加成氰化物离子，将其从氰醇原位生成到活化炔烃中。还描述了产生亚苄基环戊酮的意外的串联反应。 氰基丙烯酸酯-炔烃-催化-膦
• FLUORESCENT PROBES FOR QUANTIFICATION OF DNA DAMAGE AND REPAIR
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20210147932A1

  公开（公告）日：2021-05-20

  Probes, methods and kits for detecting and measuring abasic (AP) sites in a nucleic acid are provided. Aspects of the methods include determining glycosylase enzyme activity. Further provided herein are methods of quantifying AP sites in genomic DNA, and quantifying the amount of DNA damage. The subject probes include a fluorophore linked to an alpha nucleophile that reacts with the AP site of the nucleic acid to produce a highly fluorescent conjugate.

  提供用于检测和测量核酸中脱嘌呤（AP）位点的探针、方法和试剂盒。该方法的一些方面包括确定醇基化酶酶活性。此外，还提供了一种在基因组DNA中定量AP位点和DNA损伤量的方法。所述探针包括与α亲核试剂相连的荧光团，该试剂与核酸的AP位点发生反应，产生高度荧光的共轭物。
• IBX-Mediated Dehydrogenation of Substituted β-Oxonitriles
  作者：Philipp Klahn、Stefan F. Kirsch

  DOI：10.1002/ejoc.201402007

  日期：2014.5

  convenient method for the mild dehydrogenation of β-oxonitriles is presented. When treated with o-iodoxybenzoic acid (IBX), a range of these compounds were transformed into their unsaturated counterparts. Furthermore, we show that the products of the dehydrogenation can react in situ, undergoing rapid hetero-Diels–Alder reactions with enol ethers to give multiply substituted dihydropyrans. We also describe

  介绍了一种用于 β-氧腈温和脱氢的简便方法。当用邻碘苯甲酸 (IBX) 处理时，这些化合物中的一系列被转化为它们的不饱和对应物。此外，我们表明脱氢产物可以原位反应，与烯醇醚发生快速的杂狄尔斯-阿尔德反应，得到多取代的二氢吡喃。我们还描述了环状 β-氧腈的脱氢，这导致了取代酚的形成。
• Diels–Alder reactions of acyclic α-cyano α,β-alkenones: a new approach to highly substituted cyclohexene system
  作者：Prashanth K. Amancha、Yi-Chun Lai、I.-Chia Chen、Hsing-Jang Liu、Jia-Liang Zhu

  DOI：10.1016/j.tet.2009.11.105

  日期：2010.1

  The Diels-Alder reactions of a variety of acyclic a-cyano a,p-unsaturated ketones 8 have been investigated. With the assistance of boron trichloride, these compounds were found to undergo the cycloaddition readily with dienes to give the corresponding adducts 9 in good to high yields. In addition, some of 9 could be further subjected to the reductive alkylation reactions using lithium naphthalenide (LN) and an appropriate alkylating agent, thus allowing for the generation of highly substituted cyclohexenes 10 with the replacement of the cyano group with an alkyl substituent. (C) 2009 Elsevier Ltd. All rights reserved.