(Z)-N-benzyl-3-iodo-3-phenylprop-2-enamide | 601521-87-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-N-benzyl-3-iodo-3-phenylprop-2-enamide
• CAS: 601521-87-3
• 化学式: C₁₆H₁₄INO
• 分子量: 363.198
• InChiKey: WKORREVOKXTQGJ-PTNGSMBKSA-N

物化性质

• 沸点：
  502.1±50.0 °C(Predicted)
• 密度：
  1.540±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (Z)-N-benzyl-3-iodo-3-phenylprop-2-enamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 一氯化碘 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-Benzyl-5-[1-iodo-1-phenyl-meth-(E)-ylidene]-4-phenyl-1,5-dihydro-pyrrol-2-one
  参考文献：
  名称：

  Regioselective synthesis of 5-alkylidene and 5-(iodoalkylidene)-pyrrol-2(5H)-ones by halolactamisation of (2Z,4E)-dienamides and (Z)-alk-2-en-4-ynamides

  摘要：

  Stereo- and regioselective synthesis of 5-alkylidene (arylidene) and 5-(iodoalkylidene)-pyrrol-2(5H)-ones was achieved from (2Z,4E)-dienamides and (Z)-alk-2-en-4-ynamides by halocyclisation reaction. Selectivity was found to be highly dependent on the nature of the substituents and on the tempetature. (C) 2001 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.01.063
• 作为产物：
  描述：

  (Z)-3-iodo-3-phenyl-2-propenoic acid 、 苄胺 在 草酰氯 作用下， 生成 (Z)-N-benzyl-3-iodo-3-phenylprop-2-enamide
  参考文献：
  名称：

  Regio- and selective synthesis of 4,6-disubstituted-2-pyridones

  摘要：

  Palladium catalysed regio- and stereoselective annulation of allenyl stannanes by beta-iodo vinylic arnides gives good yields of the corresponding 2-pyridones. This annulation probably occurs via a Stille reaction/cyclisation sequence. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01429-1

文献信息

• Efficient Regio- and Stereoselective Synthesis of 5-Alkyl(aryl)idene- and 5-[Iodoalkyl(aryl)idene]-1H-pyrrol-2(5H)-ones via Electrophilic Cyclization
  作者：Mohamed Abarbri、Khalil Cherry、Alain Duchêne、Jérôme Thibonnet、Jean-Luc Parrain、Elsa Anselmi

  DOI：10.1055/s-0028-1083257

  日期：2009.1

  A variety of substituted 5-alkyl(aryl)idene- and 5-[iodoalkyl(aryl)idene]-1H-pyrrol-2(5H)-ones were readily prepared with good yields under very mild reaction conditions by the iodocyclization of (2Z,4E)-dienamides and (Z)-alk-2-en-4-ynamides with iodine monochloride. 3-Ylidene-isoindolin-1-ones were also synthesized in moderate to good yields under the same conditions. The methodology proceeded with total regioselectivity in all cases and was applied to the synthesis of new unsaturated lactam compounds.

  在非常温和的反应条件下，通过单氯化碘对（2Z,4E）-二烯酰胺和（Z）-烯-炔酰胺的碘环化，成功地合成了一系列取代的5-烷基（芳基）亚甲基和5-[碘烷基（芳基）亚甲基]-1H-吡咯-2(5H)-酮，收率良好。同时，在相同条件下，3-亚甲基-异吲哚啉-1-酮的合成也取得了中等到良好的收率。该方法在所有情况下都具有完全的区域选择性，并且被应用于新型不饱和内酰胺化合物的合成。
• Regioselective Synthesis of 1,4,6-Trisubstituted-2-Pyridinones and 2,3-Disubstituted (2<i>H</i>)-Isoquinolin-1-ones via Tandem Stille Reaction/Heterocyclisation
  作者：Mohamed Abarbri、Khalil Cherry、Alain Duchêne、Jérôme Thibonnet、Jean-Luc Parrain

  DOI：10.1055/s-2005-870009

  日期：——

  A general route to 1,4,6-trisubstituted 2-pyridinones and 2,3-disubstituted (2H)-isoquinolin-1-ones from (Z)-3-iodovinylic amides la-h and 2-iodo N-substituted benzamides 2a-f is described, including compounds bearing a substituent on the aromatic ring. Treatment of (Z)-β-iodovinylic amides la-h and 2-iodobenzamides 2a-f with various allenyltributyltin reagents in the presence of palladium acetate

  从 (Z)-3-碘乙烯基酰胺 la-h 和 2-碘 N-取代苯甲酰胺 2a 制备 1,4,6-三取代 2-吡啶酮和 2,3-二取代 (2H)-异喹啉-1-酮的一般途径描述了-f，包括在芳环上带有取代基的化合物。在乙酸钯、三苯基膦和四丁基溴化铵的存在下，在乙腈中用各种烯基三丁基锡试剂处理 (Z)-β-碘乙烯基酰胺 1a-h 和 2-碘苯甲酰胺 2a-f，得到相应的 1,4,6-三取代的良好收率2-吡啶酮 3a-k 和 2,3-二取代 (2H)-isoquinolin-1-ones 4a-i 通过串联 Stille 反应和 6-endo-dig 氮杂环化。
• Highly Efficient Access to Iminoisocoumarins and α-Iminopyrones via AgOTf-Catalyzed Intramolecular Enyne−Amide Cyclization
  作者：Ming Bian、Weijun Yao、Hanfeng Ding、Cheng Ma

  DOI：10.1021/jo9023478

  日期：2010.1.1

  Iminoisocoumarins and alpha-iminopyrones are prepared via Sonogashira coupling and AgOTf-catalyzed 6-endo-dig O-cyclization of the enyne-amide system in dichloroethane, in one pot or stepwise, respectively.
• Regioselective synthesis of 5-alkylidene and 5-(iodoalkylidene)-pyrrol-2(5H)-ones by halolactamisation of (2Z,4E)-dienamides and (Z)-alk-2-en-4-ynamides
  作者：Khalil Cherry、Jérôme Thibonnet、Alain Duchêne、Jean-Luc Parrain、Mohamed Abarbri

  DOI：10.1016/j.tetlet.2004.01.063

  日期：2004.3

  Stereo- and regioselective synthesis of 5-alkylidene (arylidene) and 5-(iodoalkylidene)-pyrrol-2(5H)-ones was achieved from (2Z,4E)-dienamides and (Z)-alk-2-en-4-ynamides by halocyclisation reaction. Selectivity was found to be highly dependent on the nature of the substituents and on the tempetature. (C) 2001 Elsevier Ltd. All rights reserved.
• Regio- and selective synthesis of 4,6-disubstituted-2-pyridones
  作者：Khalil Cherry、Mohamed Abarbri、Jean-Luc Parrain、Alain Duchêne

  DOI：10.1016/s0040-4039(03)01429-1

  日期：2003.7

  Palladium catalysed regio- and stereoselective annulation of allenyl stannanes by beta-iodo vinylic arnides gives good yields of the corresponding 2-pyridones. This annulation probably occurs via a Stille reaction/cyclisation sequence. (C) 2003 Elsevier Ltd. All rights reserved.