2,2-dimethyl-1-(thiophen-2-yl)but-3-en-1-one | 1071063-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-1-(thiophen-2-yl)but-3-en-1-one
• CAS: 1071063-68-7
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: CWYGMNCBQWNXHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-1-(thiophen-2-yl)but-3-en-1-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.5h， 生成 (E)-4,4-dimethyl-3-(thiophen-2-yl)-4,5-dihydroisoxazole-5-carbaldehyde oxime
  参考文献：
  名称：

  Iminoxyl Radical-Promoted Dichotomous Cyclizations: Efficient Oxyoximation and Aminooximation of Alkenes

  摘要：

  A novel iminoxyl radical-involved metal-free approach to vicinal oxyoximation and aminooximation of unactivated alkenes is developed. This method utilizes the dichotomous reactivity of the iminoxyl radical to furnish a general difunctionalization on alkenes using simple tert-butyl nitrite (TBN) as the iminoxyl radical initiator as well the carbon radical trap. By using this protocol, oxime featured 4,5-dihydroisoxazoles and cyclic nitrones were facilely prepared from beta,gamma- and gamma,delta-unsaturated ketoximes, respectively.

  DOI：

  10.1021/ol502258n
• 作为产物：
  描述：

  2-(2,2-dimethyl-1-hydroxy-3-buten-1-yl)thiophene 在 Jones reagent 作用下， 以 乙醚 为溶剂， 生成 2,2-dimethyl-1-(thiophen-2-yl)but-3-en-1-one
  参考文献：
  名称：

  苯肼和偶氮二羧酸酯对烯烃的自由基介导的加成反应：从环烯烃高度非对映选择性合成反式二胺

  摘要：

  不含金属的合成：在非常温和的条件下，可以通过单罐方式通过苯肼和偶氮二羧酸酯进行烯烃的胺化反应（参见方案； Boc =叔丁氧羰基）。该方法借助于自由基机理在乙酸的辅助下进行，并且当在反应中使用环烯烃底物时显示出高的反式选择性。

  DOI：

  10.1002/chem.201203832

文献信息

• Copper-Catalyzed Diamination of Alkenes of Unsaturated Ketohydrazones with Amines
  作者：Manman Chen、Li-Jing Wang、Pei-Xing Ren、Xiao-Ying Hou、Zhang Fang、Meng-Nan Han、Wei Li

  DOI：10.1021/acs.orglett.7b03401

  日期：2018.2.2

  A convenient copper-catalyzed intra-/intermolecular diamination of β,γ-unsaturated hydrazones has been developed with simple amines as external amine sources. The protocol enables efficient access to various nitrogen-containing pyrazolines under mild reaction conditions.

  用简单的胺作为外部胺源，已经开发了一种方便的铜催化的β，γ-不饱和的分子内/分子内缩醛。该协议可以在温和的反应条件下有效地获得各种含氮吡唑啉。
• A visible-light photocatalytic N-radical cascade of hydrazones for the synthesis of dihydropyrazole-fused benzosultams
  作者：Quan-Qing Zhao、Xiao-Qiang Hu、Meng-Nan Yang、Jia-Rong Chen、Wen-Jing Xiao

  DOI：10.1039/c6cc05897c

  日期：——

  An efficient N-centred radical 5-exo cyclization/addition/aromatization cascade by cooperative visible light photoredox and cobalt catalysis is described, giving dihydropyrazole-fused benzosultams in satisfactory yields.

  一个高效的N-中心自由基5-exo环化/加成/芳构化级联反应，通过可见光光合作还原和钴催化描述，产生了满意产率的二氢吡唑-螺合苯并噻唑。
• Hydrazonyl Radical-Participated Tandem Reaction: A Strategy for the Synthesis of Pyrazoline-Functionalized Oxindoles
  作者：Xiao-Yong Duan、Xiu-Long Yang、Pan-Pan Jia、Man Zhang、Bing Han

  DOI：10.1021/acs.orglett.5b03003

  日期：2015.12.18

  efficient and practical tandem cyclization/addition/cyclization strategy is developed for the initial generated hydrazonyl radicals derived from the oxidation of β,γ-unsaturated hydrazones. By using this protocol, structurally novel pyrazoline-functionalized oxindoles are prepared by the reaction of easily accessible β,γ-unsaturated hydrazones with N-aryl acrylamides under the metal- and solvent-free conditions

  针对由β，γ-不饱和的氧化衍生的初始生成的肼基自由基，开发了一种有效且实用的串联环化/加成/环化策略。通过使用该协议，结构简单的吡唑啉官能化的羟吲哚是通过使易于获得的β，γ-不饱和）与N-芳基丙烯酰胺在DTBP（无二叔丁基过氧化物）的无金属和无溶剂条件下反应而制备的。串联的分子内/分子间C–N / C–C / CC碳键形成。
• Iminoxyl Radical-Promoted Oxycyanation and Aminocyanation of Unactivated Alkenes: Synthesis of Cyano-Featured Isoxazolines and Cyclic Nitrones
  作者：Fei Chen、Fei-Fei Zhu、Man Zhang、Rui-Hua Liu、Wei Yu、Bing Han

  DOI：10.1021/acs.orglett.7b00826

  日期：2017.6.16

  oxidant, CuCN as the commercially available cyanating reagent, and pentamethyldiethylenetriamine (PMDETA) as the ligand. By using this protocol, a series of useful cyano-featured isoxazolines and cyclic nitrones were efficiently prepared.

  开发了一种新颖且简便的方法，用于内部未活化烯烃的邻位氧氰化和氨基氰化。该方法利用源自β，γ-和γ，δ-不饱和酮肟引发的亚氨基氧基的二分反应性，以叔丁基过氧化氢（TBHP）为环境友好型氧化剂，CuCN为氧化剂，提供内部烯烃的一般双官能化。市售的氰化试剂，以及五甲基二亚乙基三胺（PMDETA）作为配体。通过使用此协议，有效地制备了一系列有用的氰基特征的异恶唑啉和环状硝酮。
• Trifluoromethylthiolation and trifluoromethanesulfonylation of β,γ-unsaturated hydrazones
  作者：Hongqing Xiao、Weidong Meng、Xiu-Hua Xu、Yangen Huang

  DOI：10.1016/j.tetlet.2020.151927

  日期：2020.6

  The trifluoromethylthiolation and trifluoromethanesulfonylation of β,γ-unsaturated hydrazones was accomplished with silver(I) trifluoromethanethiolate (AgSCF3) as a CF3S source and sodium trifluoromethylsulfinate (CF3SO2Na) as a CF3SO2 source, respectively. These general methods for the preparation of dihydropyrazoles containing CF3S or CF3SO2 groups were characterized by mild reaction conditions and

  β，γ-不饱和的三氟甲硫基化和三氟甲磺酰化分别用三氟甲硫醇银（AgSCF 3）作为CF 3 S源和三氟甲亚磺酸钠（CF 3 SO 2 Na）作为CF 3 SO 2源来完成。这些制备含有CF 3 S或CF 3 SO 2基团的二氢吡唑的通用方法的特征在于温和的反应条件和良好的官能团耐受性。