cinnamoylacetonitrile | 6704-83-2

• 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: cinnamoylacetonitrile
• 英文别名: Cinnamoyl acetonitrile；3-oxo-5-phenylpent-4-enenitrile
• CAS: 6704-83-2
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: QTIZVCZKVWASSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  cinnamoylacetonitrile 在 亚硝酸 作用下， 以78%的产率得到(E)-2-[(E)-Hydroxyimino]-3-oxo-5-phenyl-pent-4-enenitrile
  参考文献：
  名称：

  Nawwar, Galal A.M.; Osman, Saad A.; El-Bayouki, Khairy A.M., Heterocycles, 1985, vol. 23, # 12, p. 2983 - 2988

  摘要：

  DOI：
• 作为产物：
  描述：

  苄叉丙酮 在 亚碘酰苯 、 三氟化硼乙醚 、 三乙胺 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 cinnamoylacetonitrile
  参考文献：
  名称：

  Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers

  摘要：

  An efficient method to synthesize beta-ketonitriles from silyl enol ethers by an umploung hypervalent iodine(III)-CN species generated in situ from PhIO/BF3 center dot Et2O/TMSCN has been developed for the first time. This method can be applied to structurally diverse aromatic and aliphatic substrates and further extended to preparation of bioactive compounds like 5-aminopyrazole and 5-aminoisoxazole.

  DOI：

  10.1021/acs.joc.5b01102

文献信息

• Doubly Activated Cyclopropanes as Synthetic Precursors for the Preparation of 4-Nitro- and 4-Cyano-dihydropyrroles and Pyrroles
  作者：Ryan P. Wurz、André B. Charette

  DOI：10.1021/ol050442l

  日期：2005.6.1

  ketones have been prepared in an expedient manner from cyclopropanation reactions of alkenes by diazo compounds or in situ-generated phenyliodonium ylides catalyzed by Rh(II) carboxylates. The doubly activated cyclopropanes were used as synthetic precursors for the regiospecific synthesis of 4-nitro- and 4-cyano-dihydropyrroles upon treatment with primary amines. Oxidation of the dihydropyrroles with DDQ

  [反应：见正文] 1-硝基和1-氰基-环丙基酮已由重氮化合物通过烯烃的环丙烷化反应或羧酸Rh（II）催化原位生成的苯基碘化碘化物，以方便的方式制备。双活化的环丙烷用作伯胺处理后4-硝基-和4-氰基-二氢吡咯的区域特异性合成的合成前体。用DDQ氧化二氢吡咯可以快速获得高密度官能化的吡咯。
• A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones
  作者：Daniel P Pienaar、Kamogelo R Butsi、Amanda L Rousseau、Dean Brady

  DOI：10.3762/bjoc.15.287

  日期：——

  The acylation of the acetonitrile anion with lactones and esters in ethereal solvents was successfully exploited using inexpensive KOt-Bu to obtain a variety of β-ketonitriles and trifunctionalized building blocks, including useful O-unprotected diols. It was discovered that lactones react to produce the corresponding derivatized cyclic hemiketals. Furthermore, the addition of a catalytic amount of

  使用廉价的KOt-Bu成功开发了醚溶剂中乙腈阴离子与内酯和酯的酰化反应，从而获得了多种β-乙腈和三官能团结构单元，包括有用的O-未保护的二醇。已发现内酯反应产生相应的衍生化的环状半缩酮。此外，必须加入催化量的异丙醇或18-crown-6，以促进反应并减少环境条件下副产物的形成。
• Unsaturated oxime derivatives and the use thereof as latent acids
  申请人：Ciba Specialty Chemicals Corporation

  公开号：US06703182B1

  公开（公告）日：2004-03-09

  Compounds of formulae I, II or III wherein m is zero or 1; n is 1, 2 or 3; R1 inter alia is unsubstituted or substituted phenyl, or naphthyl, anthracyl, phenanthryl, a heteroaryl radical, or C2-C12alkenyl; R′1 inter alia is vinylene, phenylene, naphthylene, diphenylene or oxydiphenylene; R2 inter alia is CN, C1-C4haloalkyl, C2-C6alkoxycarbonyl, phenoxycarbonyl, or benzoyl; R3 inter alia is C1-C18alkylsulfonyl, phenyl-C1-C3alkylsulfonyl, camphorylsulfonyl, or phenylsulfonyl; R′3 inter alia is C2-C12alkylenedisulfonyl, phenylenedisulfonyl, naphthylenedisulfonyl, diphenylenedisulfonyl, or oxydiphenylenedisulfonyl; R4 and R5 inter alia are hydrogen, halogen, C1-C8alkyl, C1-C6alkoxy, C1-C4haloalkyl, CN, NO2, C2-C6alkanoyl, benzoyl, phenyl, —S-phenyl, OR6, SR9, NR7R8, C2-C6alkoxycarbonyl or phenoxycarbonyl; R6 inter alia is hydrogen, phenyl or C1-C12alkyl; R7 and R8 inter alia are hydrogen or C1-C12alkyl; R9 inter alia is C1-C12 alkyl; R10, R11 and R12 inter alia are C1-C6alkyl or phenyl; upon irradiation react as acid generating compounds and thus are suitable in photoresist applications.

  化合物的公式为I、II或III，其中m为零或1；n为1、2或3；R1包括未取代或取代的苯基、萘基、蒽基、菲基、杂环基或C2-C12烯基；R′1包括乙烯基、苯基、萘基、二苯基基或氧二苯基基；R2包括CN、C1-C4卤代烷基、C2-C6烷氧羰基、苯氧羰基或苯甲酰基；R3包括C1-C18烷基磺酰基、苯基-C1-C3烷基磺酰基、樟脑基磺酰基或苯磺酰基；R′3包括C2-C12烷二磺酰基、苯基二磺酰基、萘基二磺酰基、二苯基基二磺酰基或氧二苯基基二磺酰基；R4和R5包括氢、卤素、C1-C8烷基、C1-C6烷氧基、C1-C4卤代烷基、CN、NO2、C2-C6酰基、苯甲酰基、苯基、-S-苯基、OR6、SR9、NR7R8、C2-C6烷氧羰基或苯氧羰基；R6包括氢、苯基或C1-C12烷基；R7和R8包括氢或C1-C12烷基；R9包括C1-C12烷基；R10、R11和R12包括C1-C6烷基或苯基；在辐照下反应为产生酸的化合物，因此适用于光刻胶应用。
• Enantioselective Synthesis of Dihydropyrazolo[3,4‐ <i>b</i> ]pyridin‐6‐ones via N‐Heterocyclic Carbene Catalyzed [3+3] Cycloaddition of <i>α</i> ‐Bromoenals with 5‐Aminopyrazoles
  作者：Yarui Li、Xiaoxia Huang、Jieyin He、Shiyong Peng、Jian Wang、Ming Lang

  DOI：10.1002/adsc.202201335

  日期：2023.2.21

  An N-heterocyclic carbene (NHC) catalyzed asymmetric [3+3] annulation of α-bromoenals with 5-aminopyrazoles is described. Using the established methodology, a structurally diverse set of high value dihydropyrazolo[3,4-b]pyridine-6-ones were efficiently constructed in high yields (up to 99%) with excellent enantioselectivities (up to >99%). The easily available starting materials, broad substrate scope

  描述了N-杂环卡宾 (NHC) 催化的α-溴烯醛与 5-氨基吡唑的不对称 [3+3] 环化反应。使用已建立的方法，以高产率（高达 99%）和出色的对映选择性（高达 >99%）有效地构建了一组结构多样的高价值二氢吡唑并[3,4- b ]吡啶-6-酮。易于获得的起始材料、广泛的底物范围、温和的反应条件、优异的产率和对映选择性使该策略对于吡唑并稠合吡啶酮衍生物的不对称构建具有吸引力。
• An Efficient One-Step Synthesis of 3-Oxoalkanenitriles
  作者：John C. Krauss、Thomas L. Cupps、Dean S. Wise、Leroy B. Townsend

  DOI：10.1055/s-1983-30316

  日期：——