N-(2-bromophenyl)-N-methylpropiolamide | 267408-61-7

• 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: N-(2-bromophenyl)-N-methylpropiolamide
• 英文别名: InChI=1/C10H8BrNO/c1-3-10(13)12(2)9-7-5-4-6-8(9)11/h1,4-7H,2H；N-(2-bromophenyl)-N-methylprop-2-ynamide
• CAS: 267408-61-7
• 化学式: C₁₀H₈BrNO
• 分子量: 238.084
• InChiKey: BHULBFBFOHEKCE-UHFFFAOYSA-N

物化性质

• 沸点：
  292.1±42.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-bromophenyl)-N-methylpropiolamide 在 copper(l) iodide 、 四(三苯基膦)钯 、 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3-(bis(4-nitrophenyl)methylene)-1-methylindolin-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
• 作为产物：
  描述：

  2-溴苯胺 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 19.0h， 生成 N-(2-bromophenyl)-N-methylpropiolamide
  参考文献：
  名称：

  使用微波辐射钯催化串联方法制备 3-（二芳基亚甲基）羟吲哚

  摘要：

  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。

  DOI：

  10.1055/s-0035-1560091

文献信息

• The synthesis of 3-methyleneindol-2(3H )-ones related to mitomycins via 5-exo-dig aryl radical cyclisation
  作者：Shirley A. Brunton、Keith Jones

  DOI：10.1039/a907920c

  日期：——

  The synthesis of acetylenic amides from 2-bromoaniline and propiolic acids followed by their cyclisation via the derived aryl radical is presented. Silylation of the terminal end of the triple bond is shown to be required for successful cyclisation to 3-methyleneindol-2(3H)-ones. The exocyclic double bond can be epoxidised using m-chloroperoxybenzoic acid (MCPBA).

  乙炔酰胺的合成 2-溴苯胺 和丙酸，其次是 环化 通过派生芳基 部首出现。 甲硅烷基化 三键键合的末端表明成功需要 环化至3-亚甲基吲哚-2（3H）-1。环外双键可使用以下方法环氧化间氯过氧苯甲酸 （MCPBA）。
• 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。
• Isopropanol and potassium tert-butoxide promoted intramolecular direct sp2 C–H functionalization: an expedient synthesis of 1,2,3-triazole annulated chromens and quinolones
  作者：Biplab Mondal、Brindaban Roy

  DOI：10.1016/j.tetlet.2015.09.096

  日期：2015.10

  A series of 1,2,3-triazole annulated chromen and quinolone derivatives have been synthesized by means of direct sp2 C–H functionalization in the presence of iso-propanol and potassium tert-butoxide. The reaction proceeds through homolytic aromatic substitution (HAS). This efficient as well as simple C–H functionalization methodology offers a straightforward route to 1,2,3-triazole annulated oxygen

  在异丙醇和叔丁醇钾存在下，通过直接sp 2 C–H官能化合成了一系列1,2,3-三唑环氧化铬和喹诺酮衍生物。反应通过均相芳族取代（HAS）进行。这种高效且简单的C–H功能化方法为1,2,3-三唑环氧化的氧和氮杂环化合物提供了直接的途径。
• Stereoselective Synthesis of 3-(1,3-Diarylallylidene)oxindoles via a Palladium-Catalyzed Tandem Reaction
  作者：Yoseb Yu、Kye Jung Shin、Jae Hong Seo

  DOI：10.1021/acs.joc.6b02909

  日期：2017.2.3

  We have developed an efficient three-component tandem reaction for the synthesis of 3-(1,3-diarylallylidene)oxindoles combining three palladium-catalyzed reactions: the Sonogashira, Heck, and Suzuki–Miyaura reactions. This method allows a stereoselective approach to each (E)- and (Z)-isomer by ligand change and controlling the reaction temperature.

  我们已经开发了一种有效的三组分串联反应，用于合成3-（1,3-二芳基亚烷基）氧吲哚，并结合了三种钯催化的反应：Sonogashira，Heck和Suzuki-Miyaura反应。该方法允许通过配体变化和控制反应温度对（E）-和（Z）-异构体进行立体选择。
• Synthesis of 3-(Diarylmethylene)oxindoles via a Palladium-Catalyzed One-Pot Reaction: Sonogashira-Heck-Suzuki-Miyaura Combined Reaction
  作者：Jae Seo、Guang Dong、Sunhwa Park、Dahye Lee、Kye Shin

  DOI：10.1055/s-0033-1339690

  日期：——

  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.

表征谱图