(Z)-1-methyl-3-((4-nitrophenyl)(phenyl)methylene)indolin-2-one | 1477484-70-0

• 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: (Z)-1-methyl-3-((4-nitrophenyl)(phenyl)methylene)indolin-2-one
• 英文别名: (3Z)-1-methyl-3-[(4-nitrophenyl)-phenylmethylidene]indol-2-one
• CAS: 1477484-70-0
• 化学式: C₂₂H₁₆N₂O₃
• 分子量: 356.381
• InChiKey: DDBVVYNPZXUUQB-MRCUWXFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯丙炔酸 在 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 42.5h， 生成 (E)-1-methyl-3-((4-nitrophenyl)(phenyl)methylene)indolin-2-one 、 (Z)-1-methyl-3-((4-nitrophenyl)(phenyl)methylene)indolin-2-one
  参考文献：
  名称：

  Synthesis of 3-(Diarylmethylene)oxindoles via a Palladium-Catalyzed One-Pot Reaction: Sonogashira-Heck-Suzuki-Miyaura Combined Reaction

  摘要：

  A novel one-pot reaction for the synthesis of 3-(diarylmethylene)oxindoles is described. The reaction involves the successive combination of three palladium-catalyzed reactions (Sonogashira, Heck, and Suzuki-Miyaura reactions). This method enables the rapid synthesis of various 3-(diarylmethylene)oxindoles from simple propiolamides. The addition of silver salts dramatically enhanced the E/Z stereoselectivity of the reaction.

  DOI：

  10.1055/s-0033-1339690

文献信息

• Palladium-Catalyzed One-Pot Approach to 3-(Diarylmethylene)oxindoles from Propiolamidoaryl Triflate
  作者：Dahye Lee、Sunhwa Park、Yoseb Yu、Kye Shin、Jae Seo

  DOI：10.3390/molecules200814022

  日期：——

  3-(Diarylmethylene)oxindoles have been synthesized from propiolamidoaryl triflate utilizing a palladium-catalyzed one-pot reaction consisting of three successive reactions: Sonogashira, Heck, and Suzuki-Miyaura. This method allows for the production of a complex skeleton of 3-(diarylmethylene)oxindole from propiolamidoaryl triflate using a commercially available aryl iodide and arylboronic acid in a simple and efficient way with moderate yield and stereoselectivity.

  通过丙炔酰胺基芳基三氟甲磺酸盐的钯催化一步反应，包括三个连续反应：Sonogashira反应、Heck反应和Suzuki-Miyaura反应，合成得到了3-(二芳甲叉基)吲哚。该方法使得从商业上可获得的芳基碘和芳基硼酸出发，通过简单高效的方式，以中等产率和立体选择性，从丙炔酰胺基芳基三氟甲磺酸盐合成得到3-(二芳甲叉基)吲哚的复杂骨架。
• Palladium-Catalyzed Tandem Approach to 3-(Diarylmethylene)oxindoles Using Microwave Irradiation
  作者：Jae Seo、Sunhwa Park、Kye Shin

  DOI：10.1055/s-0035-1560091

  日期：——

  We developed a rapid and efficient microwave-assisted tandem reaction for the synthesis of 3-(diarylmethylene)oxindoles. Three palladium-catalyzed reactions (Sonogashira, Heck, and Suzuki–Miyaura reactions) were combined under microwave irradiation conditions to produce 3-(diarylmethylene)oxindoles from simple propiolamides, aryl iodides, and arylboronic acids. The addition of Ag 3 PO 4 enhanced the

  我们开发了一种快速有效的微波辅助串联反应，用于合成 3-（二芳基亚甲基）羟吲哚。三个钯催化的反应（Sonogashira、Heck 和 Suzuki-Miyaura 反应）在微波辐射条件下结合，从简单的丙酰胺、芳基碘和芳基硼酸生产 3-（二芳基亚甲基）羟吲哚。Ag 3 PO 4 的加入显着提高了串联反应的产率和立体选择性。
• Consecutive One-Pot versus Domino Multicomponent Approaches to 3-(Diarylmethylene)oxindoles
  作者：Sunhwa Park、Jiyun Lee、Kye Shin、Euichaul Oh、Jae Seo

  DOI：10.3390/molecules22030503

  日期：——

  reactions (Sonogashira, Heck and Suzuki-Miyaura reactions), a more efficient domino multicomponent method has been successfully developed to access a wide variety of 3-(diarylmethylene)oxindoles. Microwave irradiation and use of a silver salt were the most important factors to achieve high yields and stereoselectivity.

  基于结合三个钯催化反应（Sonogashira、Heck 和 Suzuki-Miyaura 反应）的连续一锅条件，已成功开发出一种更有效的多米诺多组分方法来获取各种 3-（二芳基亚甲基）羟吲哚。微波辐射和银盐的使用是实现高产率和立体选择性的最重要因素。