3-phenyl-N-(3-chlorophenyl)propynamide | 343596-13-4

• 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-phenyl-N-(3-chlorophenyl)propynamide
• 英文别名: N-(3-chlorophenyl)-3-phenylpropiolamide；N-(3-chlorophenyl)-3-phenylprop-2-ynamide
• CAS: 343596-13-4
• 化学式: C₁₅H₁₀ClNO
• mdl: MFCD08071120
• 分子量: 255.703
• InChiKey: PLOQWXAEEVIHPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-phenyl-N-(3-chlorophenyl)propynamide 在 叔丁基过氧化氢 、 manganese(IV) oxide 、 sodium acetate 、 sodium hydride 、 copper(l) chloride 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 10.5h， 生成 7-chloro-1-methyl-4-phenyl-3-(trifluoromethyl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione
  参考文献：
  名称：

  通过自由基氧化-串联环化/脱芳香化反应催化活性的炔烃的铜催化双官能团合成3-三氟甲基螺[4.5]三烯酮

  摘要：

  已经开发了一种采用串联环化/脱芳香化工艺的廉价催化剂三氟甲烷亚磺酸钠（NaSO 2 CF 3或Langlois试剂）对活化炔烃进行铜催化的双官能化三氟甲基化反应。该策略为3-（三氟甲基）-螺[4.5]三烯酮的合成提供了一条直接途径，并给出了炔烃双官能化的示例，以同时形成两个碳-碳单键和一个碳-氧双键。

  DOI：

  10.1002/chem.201405672
• 作为产物：
  描述：

  苯丙炔酸 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 3-phenyl-N-(3-chlorophenyl)propynamide
  参考文献：
  名称：

  2,5-Diarylisothiazolone: novel inhibitors of cytokine-induced cartilage destruction

  摘要：

  A series of 2,5-diarylisothiazolones is reported that inhibit the IL-lp-induced breakdown of bovine nasal septum cartilage in an organ culture assay. The synthesis and preliminary SAR of these compounds are described. These compounds represent a novel, nonpeptide lead series approach to the mediation of the chronic cartilage breakdown associated with arthritic disease. These compounds are relatively resistant to reductive metabolism by liver microsomal preparations and appear to inhibit cartilage breakdown by interfering with the proteolytic activation of matrix metalloproteinases. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00053-3

文献信息

• Transition-metal and base-free thioannulation of propynamides with sodium sulfide and dichloromethane for the selective synthesis of 1,3-thiazin-4-ones and thiazolidine-4-ones
  作者：Sui-Qian Wang、Xiao-Wei Yan、Bo-Lun Hu、Xing-Guo Zhang

  DOI：10.1016/j.tet.2020.131021

  日期：2020.3

  A thioannulation of propynamides with sodium sulfide and CH2Cl2 in the absence of transition-metal and base has been established. This one-pot tandem reaction provides a facile and efficient method for the selective synthesis of 1,3-thiazide-4-ones or thiazolidine-4-ones through constructing both C–N and C–S bonds. The atom-economic reaction features mild conditions and good functional group tolerance

  已经建立了在不存在过渡金属和碱的情况下用硫化钠和CH 2 Cl 2进行丙炔酰胺的硫代环化反应。这一一锅串联反应为通过构建C–N和C–S键选择性合成1,3-噻嗪4-酮或噻唑烷4-酮提供了一种简便而有效的方法。原子经济反应具有温和的条件和良好的官能团耐受性，并使用廉价，安全和无味的硫源。
• A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles
  作者：Vikas Dwivedi、Manda Rajesh、Ravi Kumar、Ruchir Kant、Maddi Sridhar Reddy

  DOI：10.1039/c7cc06081e

  日期：——

  A regio- and stereoselective thiocyanate addition to ynones is achieved using KSCN in AcOH at 70 °C. The reaction is extendable to ynals, ynesulfones, ynoic acids and ynoates. Adducts from ynones were readily transformed into thiazine-2-thione derivatives under slightly modified reaction conditions. In contrast, thiocyanated adducts from ynamides underwent an in situ decyanative amido cyclization towards

  使用KSCN在70°C的AcOH中，向炔酮中进行区域和立体选择性的硫氰酸酯加成反应。该反应可扩展至乙醛，乙炔砜，山药酸和山药。在稍微改变的反应条件下，来自炔酮的加合物很容易转化为噻嗪-2-硫酮衍生物。相反，来自酰胺的硫氰化加合物向异噻唑酮进行原位脱氰酰胺环化反应。这些事件均不需要任何过渡金属或催化剂，即可获得较高的合成价值。
• (<i>Z</i>)-Selective anti-Markovnikov or Markovnikov thiol–yne-click reactions of an internal alkyne by amide hydrogen bond control
  作者：Milan Pramanik、Khokan Choudhuri、Subhayan Chakraborty、Arindam Ghosh、Prasenjit Mal

  DOI：10.1039/d0cc00702a

  日期：——

  Herein, we show exclusive control of stereo and regioselective thiol-yne click (TYC) reactions of internal alkynes via amide hydrogen bond control. By exploiting appropriate hydrogen bonding interactions like N-HS, N-HN and C-HO, either (Z)-selective anti-Markovnikov or Markovnikov products could be obtained for an internal alkyne, exclusively.

  在本文中，我们显示了通过酰胺氢键控制对内部炔烃的立体和区域选择性硫醇-炔点击（TYC）反应的排他性控制。通过利用适当的氢键相互作用（例如N-HS，N-HN和C-HO），可以仅针对内部炔烃获得（Z）选择性反马尔科夫尼科夫或马尔科夫尼科夫产物。
• Palladium-Catalyzed Carbo-Aminative Cyclization of 1,6-Enynes: Access to Napthyridinone Derivatives
  作者：Undamatla Suri Babu、Maneesh Kumar Reddy Singam、Muniganti Naveen Kumar、Jagadeesh Babu Nanubolu、Maddi Sridhar Reddy

  DOI：10.1021/acs.orglett.2c00088

  日期：2022.3.4

  We describe herein a general approach to napthyridinones via the Pd-catalyzed annulation of 1,6-enynes with 2-iodoanilines. This protocol represents a rare carbo-aminative annulative cyclization via the 6-endo-trig mode, subduing the well-documented exo-trig/dig cyclizations. The regioselective aryl palladation of alkyne followed by Heck-type intramolecular coupling before isomerization were key in

  1,6-Enynes 最近引起了极大的关注，为独特的级联环化铺平了道路，提供了来自线性底物的复杂环状基序。我们在此描述了通过 Pd 催化的 1,6-烯炔与 2-碘苯胺的环化来制备萘啶酮的一般方法。该协议通过 6-endo-trig 模式代表了一种罕见的碳胺环化环化，抑制了有据可查的 exo-trig/dig 环化。炔烃的区域选择性芳基钯化，然后是异构化之前的 Heck 型分子内偶联是实现这种级联的关键。
• Copper‐Catalyzed Thioannulation of Propynamides with Sodium Sulfide for the Synthesis of Isothiazol‐3‐ones
  作者：Sui‐Qian Wang、Bo‐Lun Hu、Xing‐Guo Zhang

  DOI：10.1002/adsc.201801579

  日期：2019.3.15

  A method for the copper‐catalyzed thioannulation of propynamides with sodium sulfide was developed for the synthesis of isothiazol‐3‐ones. The reaction involves a nucleophilic addition and an intramolecular cross‐dehydrogenative coupling reaction. The thioannulation features the use of an inexpensive and odorless sulfur source and easily prepared propynamides with excellent functional group tolerance

  开发了一种用硫化钠铜催化的丙酰胺酰胺硫代环化反应的方法，用于合成异噻唑-3-酮。该反应涉及亲核加成和分子内交叉脱氢偶联反应。硫代环化的特点是使用廉价且无味的硫源，并易于制备具有出色的官能团耐受性的丙酰胺。