3-(2-formylphenyl)-N-methyl-N-phenylpropiolamide | 1238625-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-formylphenyl)-N-methyl-N-phenylpropiolamide
• 英文别名: 3-(2-formylphenyl)-N-methyl-N-phenylprop-2-ynamide
• CAS: 1238625-83-6
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: LILITZWJVBTLCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-formylphenyl)-N-methyl-N-phenylpropiolamide 在 盐酸 、 4,4'-二甲氧基-2,2'-联吡啶 、 palladium diacetate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 2.08h， 生成 3-hydroxy-1-indanone
  参考文献：
  名称：

  乙酸钯（II）催化乙酸向正电子缺失的炔基取代的芳醛中意外添加乙酸

  摘要：

  AbstractAn unexpected addition of acetic acid to ortho‐electron‐deficient alkynyl‐substituted aryl aldehydes catalyzed by palladium(II) acetate was achieved, which provided a convenient method for the synthesis of dihydroisobenzofurans in moderate to good yields. The electron‐withdrawing groups attached to alkynes may play an important role for the cyclization.magnified image

  DOI：

  10.1002/adsc.201301170
• 作为产物：
  描述：

  3-iodo-N-methyl-N-phenylpropynamide 、 2-甲酰基苯硼酸 在 palladium diacetate 、 caesium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以63%的产率得到3-(2-formylphenyl)-N-methyl-N-phenylpropiolamide
  参考文献：
  名称：

  需氧条件下高效钯催化碘代乙炔与芳基硼酸的铃木-宫浦交叉偶联

  摘要：

  在有氧条件下，开发了无配体钯催化的碘乙炔与芳基硼酸的铃木-宫浦交叉偶联。在乙酸钯（II）和碳酸铯的存在下，各种碘乙炔在室温下与芳基硼酸进行了Suzuki-Miyaura交叉偶联反应，以中等至良好的收率提供了相应的内部炔烃。值得注意的是，该方案在温和有氧条件下进行而无需配体的帮助。 钯-碘乙炔-芳基硼酸-铃木宫浦-交叉偶联-炔烃

  DOI：

  10.1055/s-0030-1260126

文献信息

• Palladium-Catalyzed Cross-Coupling of Electron-Poor Terminal Alkynes with Arylboronic Acids under Ligand-Free and Aerobic Conditions
  作者：Ming-Bo Zhou、Wen-Ting Wei、Ye-Xiang Xie、Yong Lei、Jin-Heng Li

  DOI：10.1021/jo101063p

  日期：2010.8.20

  Palladium-catalyzed cross-coupling reaction of terminal alkynes with arylboronic acids has been described. In the presence of Pd(OAc)2 and Ag2O, a variety of terminal alkynes, including electron-poor terminal alkynes, smoothly underwent the reaction with numerous boronic acids to afford the corresponding internal alkynes in moderate to good yields. Moreover, this methodology was applied to the synthesis

  已经描述了末端炔与芳基硼酸的钯催化的交叉偶联反应。在Pd（OAc）2和Ag 2 O的存在下，包括电子贫乏的末端炔在内的各种末端炔与许多硼酸的反应顺利进行，从而以中等至良好的收率提供了相应的内部炔。而且，该方法学被用于1 H-异苯并二酮和二炔的合成。值得注意的是，反应在无配体和相对较低的负载Pd条件下进行，反应的最大TON（转化数）高达720,000。
• Synthesis of Indole-Substituted Indanones via Palladium(II)-Catalyzed Tandem Reaction of<i>ortho</i>-Electron-Deficient Alkynyl-Substituted Aryl Aldehydes with Indoles
  作者：Jianbo Zhang、Xiuling Han、Xiyan Lu

  DOI：10.1021/acs.orglett.6b01240

  日期：2016.6.17

  A Pd(OAc)2-catalyzed cyclization reaction of ortho-electron-deficient alkynyl-substituted aryl aldehydes with indoles was accomplished, providing an efficient and economical way to synthesize indole-substituted indanones. The electron-withdrawing group attached to the alkyne and the nucleophilic indole play important roles in the formation of the indanone ring.

  甲的Pd（OAC）2的催化的环化反应的邻与吲哚π电子缺乏的炔基取代的芳基醛中完成的，提供一种有效且经济的方式来合成吲哚取代的茚满酮。附接到炔烃和亲核吲哚的吸电子基团在茚满酮环的形成中起重要作用。
• An Unexpected Addition of Acetic Acid to<i>ortho</i>-Electron- Deficient Alkynyl-Substituted Aryl Aldehydes Catalyzed by Palladium(II) Acetate
  作者：Jianbo Zhang、Xiuling Han

  DOI：10.1002/adsc.201301170

  日期：2014.8.11

  AbstractAn unexpected addition of acetic acid to ortho‐electron‐deficient alkynyl‐substituted aryl aldehydes catalyzed by palladium(II) acetate was achieved, which provided a convenient method for the synthesis of dihydroisobenzofurans in moderate to good yields. The electron‐withdrawing groups attached to alkynes may play an important role for the cyclization.magnified image
• Efficient Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Iodoethynes with Arylboronic Acids under Aerobic Conditions
  作者：Jian-Sheng Tang、Jin-Heng Li、Ye-Xiang Xie、Zhi-Qiang Wang

  DOI：10.1055/s-0030-1260126

  日期：2011.9

  iodoethynes with arylboronic acids under aerobic conditions has been developed. In the presence of palladium(II) acetate and cesium carbonate, a variety of iodoethynes underwent the Suzuki­-Miyaura cross-coupling reaction with arylboronic acids at room temperature to afford the corresponding internal alkynes in moderate to good yields. It is noteworthy that this protocol proceeds under mild and aerobic conditions

  在有氧条件下，开发了无配体钯催化的碘乙炔与芳基硼酸的铃木-宫浦交叉偶联。在乙酸钯（II）和碳酸铯的存在下，各种碘乙炔在室温下与芳基硼酸进行了Suzuki-Miyaura交叉偶联反应，以中等至良好的收率提供了相应的内部炔烃。值得注意的是，该方案在温和有氧条件下进行而无需配体的帮助。 钯-碘乙炔-芳基硼酸-铃木宫浦-交叉偶联-炔烃