3-(4-acetylphenyl)propiolaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-acetylphenyl)propiolaldehyde
• 英文别名: 4-acetylphenylpropynal；3-(4-Acetylphenyl)prop-2-ynal
• 化学式: C₁₁H₈O₂
• 分子量: 172.183
• InChiKey: SVHAXURPCHYODN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-acetylphenyl)propiolaldehyde 在 三乙烯二胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 methyl 3-acetoxy-5-(4-acetylphenyl)-2-methylenepent-4-ynoate
  参考文献：
  名称：

  Cu(I)-Catalyzed Aminative Aza-Annulation of Enynyl Azide using N-Fluorobenzenesulfonimide: Synthesis of 5-Aminonicotinates

  摘要：

  An unprecedented copper-catalyzed aminative aza-annulation of enynyl azide using commercially available N-fluorobenzenesulfonhnide (NFSI) as an amination reagent is described. The reaction proceeds via regioselective inter-/intramolecular diamination, incorporating one nitrogen from the NFSI and the other from the azide, to provide amino substituted nicotinate derivatives in a single step with moderate to high yield. This method represents an efficient way to access diverse aminonicotinates through direct C-N bond-coupling processes.

  DOI：

  10.1021/acs.orglett.8b01228
• 作为产物：
  描述：

  1-[4-(3-羟基丙-1-炔基)苯基]乙酮 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 3-(4-acetylphenyl)propiolaldehyde
  参考文献：
  名称：

  锌催化的[4 + 3]环加成反应及呋喃环化反应：环庚[b]呋喃的形成

  摘要：

  首先实现了一种简单的锌促进的羰基烯-炔的锌促进的[4 + 3]环加成反应。该反应提供了通过级联环加成反应制备各种环庚[ b ]呋喃环的有效策略。此外，二酮，炔醛，和二烯的多组分反应也有报道，其显示了用于使C选择性创作的新策略 O键和C  C键。

  DOI：

  10.1002/chem.201402513

文献信息

• Controllable Site-Selective Construction of 2- and 4-Substituted Pyrimido[1,2-<i>b</i>]indazole from 3-Aminoindazoles and Ynals
  作者：Xiang Liu、Jinlei Zhou、Jiatong Lin、Zemin Zhang、Suying Wu、Qiuxing He、Hua Cao

  DOI：10.1021/acs.joc.1c01094

  日期：2021.7.2

  straightforward and novel controllable site-selective construction of 2- and 4-substituted pyrimido[1,2-b]indazole from 3-aminoindazoles and ynals has been developed. The high regioselectivity of this reaction could be easily switched by converting different catalytic systems. In this way, a series of 2- and 4-substituted pyrimido[1,2-b]indazole derivatives were obtained in moderate to good yields. In addition, the

  已经开发出一种由 3-氨基吲唑和 ynals 直接且新颖的可控位点选择性构建 2-和 4-取代的嘧啶并[1,2 -b ]吲唑的方法。该反应的高区域选择性可以通过转换不同的催化体系轻松切换。通过这种方式，以中等至良好的收率获得了一系列2-和4-取代的嘧啶并[1,2- b ]吲唑衍生物。此外，还讨论了本方法制备的化合物3a的光物理性质。
• Rhodium-Catalyzed 1,1-Hydroacylation of Thioacyl Carbenes with Alkynyl Aldehydes and Subsequent Cyclization
  作者：Bingnan Zhou、Qiuyue Wu、Ziyang Dong、Jiaxi Xu、Zhanhui Yang

  DOI：10.1021/acs.orglett.9b01003

  日期：2019.5.17

  A rhodium-catalyzed 1,1-hydroacylation of thioacyl carbenes with alkynyl and alkenyl aldehydes and subsequent 6-endo-trig/dig cyclization are realized, giving structurally diverse 4H-thiopyran-4-ones and 2,3-dihydro-4H-thiopyran-4-ones in moderate to good yields. The oxidative addition of Rh(I) to aldehydes is proposed to be the turnover-limiting step. Manipulations of estrones demonstrate the applications

  实现了铑的羰基羰基与炔基和烯基醛催化的1,1-氢羰基化反应，随后进行了6-内-trig / dig环化反应，得到了结构上不同的4 H - thiopyran -4-ones和2,3-dihydro-4 H -thiopyran-4-ones，产量中等至良好。提出将Rh（I）氧化成醛是限制营业额的步骤。雌酮的操作证明了我们正式的（3 + 3）转环剂在天然产物的结构修饰中的应用。
• An Efficient and Versatile Approach for the Immobilization of Carbene Precursorsvia Copper-Catalyzed [3+2]-Cycloaddition and their Catalytic Application
  作者：Kirsten Zeitler、Ina Mager

  DOI：10.1002/adsc.200700174

  日期：2007.8.6

  azide-functionalized support via copper-catalyzed 1,3-dipolar cycloaddition, which efficiently yields a rigid and robust 1,2,3-triazole linkage. The catalytic performance of the corresponding nucleophilic carbenes (NHCs) was examined in intramolecular Stetter reactions (chroman-4-one products) and organocatalytic redox esterifications (α,β-unsaturated esters). The MeOPEG-immobilized organocatalysts are

  可以通过铜催化的1,3-偶极环加成将不同种类的炔基取代的杂唑衍生物共价固定在叠氮化物官能化的支持物上，这有效地产生了刚性且牢固的1,2,3-三唑键。在分子内Stetter反应（苯并四氢呋喃产物）和有机催化氧化还原酯化反应（α，β-不饱和酯）中检查了相应亲核碳烯（NHC）的催化性能。固定有MeOPEG的有机催化剂具有很高的活性，并显示出与非负载衍生物相当的非对映选择性。此外，它们还简化了后处理程序，并且已被证明可回收利用。
• Zinc-Catalyzed [4+3] Cycloaddition with Concomitant Furan Annulation: Formation of Cyclohepta[<i>b</i>]Furans
  作者：Bo Song、Lian-Hua Li、Xian-Rong Song、Yi-Feng Qiu、Mei-Jin Zhong、Ping-Xin Zhou、Yong-Min Liang

  DOI：10.1002/chem.201402513

  日期：2014.5.12

  A convenient zinc‐promoted [4+3] cycloaddition of a carbonyl ene–yne with simple dienes was first achieved. This reaction provided an efficient strategy to prepare various cyclohepta[b]furan rings by cascade cycloadditions. Additionally, a multicomponent reaction of dione, alkynal, and diene was also reported, which exhibited a novel strategy for selective creations of CO bonds and CC bonds.

  首先实现了一种简单的锌促进的羰基烯-炔的锌促进的[4 + 3]环加成反应。该反应提供了通过级联环加成反应制备各种环庚[ b ]呋喃环的有效策略。此外，二酮，炔醛，和二烯的多组分反应也有报道，其显示了用于使C选择性创作的新策略 O键和C  C键。
• Transition-metal-free highly efficient synthesis of 2-pyridones from β-keto amides and ynals
  作者：Zhengwang Chen、Jiayang Liu、Caiju Jin、Qi Tan、Min Ye

  DOI：10.1016/j.tetlet.2019.04.001

  日期：2019.5

  A convenient and efficient annulation reaction was developed, affording 2-pyridones in good to excellent yields. A variety of substituted β-keto amides and ynals were well tolerated, and especially the transformation produced water as only by-product under transition-metal-free conditions. Furthermore, the conjugated enyneamides were achieved from β-cyano amides and ynals in high yields.

  开发了一种方便而有效的环化反应，以良好的产率获得了2-吡啶酮。多种取代的β-酮酰胺和ynal具有良好的耐受性，尤其是在无过渡金属的条件下，该转化产生的水仅作为副产物。此外，从β-氰基酰胺和ynals以高收率获得了共轭烯炔酰胺。