(4-nitrophenyl)(thiophen-3-yl)methanone | 1018902-97-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-nitrophenyl)(thiophen-3-yl)methanone
• 英文别名: 3-(4-nitrobenzoyl) thiophene；(4-Nitrophenyl)-thiophen-3-ylmethanone
• CAS: 1018902-97-0
• 化学式: C₁₁H₇NO₃S
• 分子量: 233.247
• InChiKey: GDNVGONOTPMUBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-硝基苯甲酰氯 在 4-二甲氨基吡啶 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (4-nitrophenyl)(thiophen-3-yl)methanone
  参考文献：
  名称：

  通过高化学选择性 N-C 裂解的机械化学无溶剂 Suzuki-Miyaura 酰胺交叉偶联

  摘要：

  报道了第一个通过 N-C 键活化实现高化学选择性、无溶剂钯催化的酰胺交叉偶联的机械化学策略。该协议将生物相关的酰胺键交叉耦合歧管推进到固态无溶剂交叉耦合方法。

  DOI：

  10.1002/anie.202114146

文献信息

• Magnesium salt promoted tandem nucleophilic addition–Oppenauer oxidation of aldehydes with organozinc reagents
  作者：Ying Fu、Xing Ling Zhao、Hulmet Hügel、Danfeng Huang、Zhengyin Du、Kehu Wang、Yulai Hu

  DOI：10.1039/c6ob01668e

  日期：——

  A magnesium salt promoted synthesis of ketones via tandem nucleophilic addition–Oppenauer oxidation of aldehydes using organozinc chemistry was demonstrated. Magnesium salts concomitantly generated via magnesium metal mediated organohalide zincation exhibit high efficacy for nucleophilic addition of organozinc reagents to aromatic aldehydes and thereafter Oppenauer oxidation whereby ketones are formed

  证明了镁盐可通过串联亲核加成促进醛的合成-使用有机锌化学对醛进行Oppenauer氧化。通过镁金属介导的有机卤化物锌化同时生成的镁盐具有将有机锌试剂亲核加成到芳族醛中并随后进行Oppenauer氧化的高效率，从而高产率地形成酮。
• MeZnOMe-mediated reaction of aldehydes with Grignard reagents: A glance into nucleophilic addition/Oppenauer oxidation pathway
  作者：Ying Fu、Xian-Zhen Ma、Chun-Zhao Shi、Tong Shen、Zhengyin Du

  DOI：10.1002/aoc.4462

  日期：2018.9

  A novel organozincate of RMgX ⋅MeZnOMe ⋅LiCl type, formed in situ via transmetalation of Grignard reagent RMgBr ⋅LiCl with MeZnOMe, is shown to be an excellent organometallic species in the nucleophilic addition/Oppenauer oxidation of aldehydes to generate aromatic ketones in high yield. This transformation allows quick access to structurally diverse aryl, heteroaryl, benzyl and alkyl ketones with

  通过格氏试剂RMgBr·LiCl与MeZnOMe的金属转移就地形成的新型RMgX·MeZnOMe·LiCl型有机锌盐，是醛类亲核加成/ Oppenauer氧化以高产率生成芳族酮的绝佳有机金属物种。这种转变可以快速获得结构多样的芳基，杂芳基，苄基和烷基酮，具有广泛的底物范围和出色的官能团耐受性。
• Transition metal-free Suzuki type cross-coupling reaction for the synthesis of dissymmetric ketones
  作者：Sanjay Jadhav、Gajanan Rashinkar、Rajashri Salunkhe、Arjun Kumbhar

  DOI：10.1016/j.tetlet.2017.06.048

  日期：2017.8

  A simple, efficient and metal-free route for the synthesis of dissymmetric ketones through Suzuki type cross-coupling reaction has been established. This strategy signifies an attractive, cost-effective and operationally convenient tool for the synthesis of a wide range of dissymmetric ketones. Although conventional routes for the synthesis of ketones have been widely used, the potential challenge

  建立了通过Suzuki型交叉偶联反应合成不对称酮的简单，有效且无金属的途径。该策略标志着一种有吸引力的，具有成本效益且操作方便的工具，可用于合成各种不对称酮。尽管已经广泛使用了合成酮的常规方法，但是这些方法的潜在挑战是官能团的耐受性。报道的无金属方法代表具有中等官能团耐受性的反应。该程序操作方便，显示了广泛的基材范围，具有良好或优异的产品良率。
• Tandem nucleophilic addition–Oppenauer oxidation of aromatic aldehydes to aryl ketones with triorganoaluminium reagents
  作者：Ying Fu、Yanshou Yang、Helmut M. Hügel、Zhengyin Du、Kehu Wang、Danfeng Huang、Yulai Hu

  DOI：10.1039/c3ob40642c

  日期：——

  In the presence of pinacolone, the in situ prepared triorganoaluminium reagents reacted with aromatic aldehydes to give ketones in moderate to high yield. We propose that the products are formed via a tandem organoaluminium reagents addition–Oppenauer oxidation sequence.

  在频哪酮的存在下，原位制备的三有机铝试剂与芳族醛反应，以中等至高收率得到酮。我们建议这些产物是通过有机铝串联试剂-Oppenauer氧化顺序形成的。
• One-pot synthesis of diaryl ketones from aldehydes via palladium-catalyzed reaction with aryl boronic acids
  作者：Changming Qin、Jiuxi Chen、Huayue Wu、Jiang Cheng、Qiang Zhang、Bing Zuo、Weike Su、Jinchang Ding

  DOI：10.1016/j.tetlet.2007.12.074

  日期：2008.3

  aldehydes and organoboronic acids was achieved in the presence of P(1-nap)3, using Cs2CO3 in toluene, providing diaryl ketones with yields ranged from moderate to excellent. The efficiency of this reaction was demonstrated by the compatibility with nitro, cyano, trifluoromethyl, fluoro and chloro groups. Moreover, the rigorous exclusion of air/moisture is not required in these transformations.

  在甲苯中使用Cs 2 CO 3在P（1-nap）3的存在下，实现了Pd催化的醛与有机硼酸的偶联型反应，提供了产率从中等到优异的二芳基酮。通过与硝基，氰基，三氟甲基，氟和氯基团的相容性证明了该反应的效率。此外，在这些转换中不需要严格排除空气/水分。