2,3-di-(n-propyl)-4-phenyl-2-buten-4-olide | 163355-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2,3-di-(n-propyl)-4-phenyl-2-buten-4-olide
• 英文别名: 5-phenyl-3,4-dipropylfuran-2(3H)-one；5-phenyl-3,4-dipropylfuran-2(5H)-one；2(5H)-Furanone, 5-phenyl-3,4-dipropyl-；2-phenyl-3,4-dipropyl-2H-furan-5-one
• CAS: 163355-48-4
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: FHYKRJQDUMZNKV-UHFFFAOYSA-N

物化性质

• 沸点：
  396.4±31.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  一氧化碳 、 (Z)-3-iodo-1-phenyl-2-(n-propyl)-2-hexen-1-one 在 bis-triphenylphosphine-palladium(II) chloride 、 水 、 三乙胺 作用下， 以 苯 为溶剂， 120.0 ℃ 、2.03 MPa 条件下， 反应 12.0h， 以84%的产率得到2,3-di-(n-propyl)-4-phenyl-2-buten-4-olide
  参考文献：
  名称：

  Acylpalladation of Internal Alkynes and Palladium-Catalyzed Carbonylation of (Z)-.beta.-Iodoenones and Related Derivatives Producing .gamma.-Lactones and .gamma.-Lactams

  摘要：

  The reaction of either an internal alkyne-organic halide mixture or (Z)-beta-iodoenones with CO in the presence of a Pd-phosphine catalyst, e.g., Cl2Pd(PPh(3))2, can give one of the three discrete types of compounds as the major products depending on the substrate structure and the reaction conditions. Those substrates which are convertible to (Z)-gamma-oxo-alpha,beta-unsaturated acylpalladium derivatives lacking delta-H atoms are converted to the corresponding 2-butenolides (13) in the presence of water, which serves as a H donor. Carbon monoxide most likely is the source of two electrons. Either in the absence of water (or any other suitable H source) or in the presence of some factors disfavoring the butenolide formation, the same reaction gives the corresponding dimeric product (16). Even in cases where there is an alpha-H atom in the alpha-substitutent, 1,4-elimination products (11), reported to be the major products in a related Pd-catalyzed reaction of terminal alkyne-aryl iodide mixtures with CO, were not detected. In sharp contrast, those substrates which can give rise to (Z)-gamma-oxo-alpha, beta-unsaturated acylpalladium derivatives containing delta-H atoms give, under comparable reaction conditions, enol lactones (12), i.e., (Z)-3-alkylidene-2-butenolides, contaminated with only very minor amounts of 22 even in cases where an excess (4 equiv) of water was present. The required (Z)-beta-iodoenones can be readily prepared in one pot via ZrCp(2)-promoted cyclization of alkynes with nitriles. The ready availability of the starting compounds and the high Z stereoselectivity make the overall sequence an attractive synthetic route to 12. The courses of the Pd-catalyzed carbonylation reactions of (Z)-beta-iodo-alpha,beta-unsaturated imines 23 closely parallel the reactions of enones and produce the corresponding lactams, i.e., 24 and 25.

  DOI：

  10.1021/ja00117a011

文献信息

• Rhodium catalyzed reaction of internal alkynes with organoborons under CO atmosphere: a product tunable reaction
  作者：Levent Artok、Melih Kuş、Özge Aksın-Artok、Fatma Nurcan Dege、Fatma Yelda Özkılınç

  DOI：10.1016/j.tet.2009.09.044

  日期：2009.11

  Alkynes react with organoborons under a CO atmosphere in the presence of a rhodium(I) catalyst to afford mainly 5-aryl-2(5H)-furanones, α,β-unsaturated ketones, and indanones. The product selectivity can be tuned by modifying the reaction conditions.

  炔烃在铑（I）催化剂存在下，在CO气氛下与有机硼反应，主要生成5-芳基-2（5 H）-呋喃酮，α，β-不饱和酮和茚满酮。产物的选择性可以通过改变反应条件来调节。
• Rhodium-catalyzed carbonylative arylation of alkynes with arylboronic acids: an efficient and straightforward method in the synthesis of 5-aryl-2(5H)-furanones
  作者：Özge Aksın、Nurcan Dege、Levent Artok、Hayati Türkmen、Bekir Çetinkaya

  DOI：10.1039/b604742d

  日期：——

  5-Aryl-2(5H)-furanones can be synthesized by the Rh-catalyzed reactions of arylboronic acids with internal alkynes under a CO atmosphere.

  5-芳基-2(5H)-呋喃酮可以通过在CO气氛下，使用Rh催化的芳基硼酸与内炔的反应合成。
• Titanium-Mediated Carboxylation of Alkynes With Carbon Dioxide
  作者：Yvan Six

  DOI：10.1002/ejoc.200390170

  日期：2003.3

  The regioselective carboxylation of nonactivated internal alkynes can be performed with carbon dioxide under atmospheric pressure using a simple procedure based on the chemistry of Sato-type diisopropyloxytitanacyclopropenes. Various polysubstituted vinylcarboxylic acids and butenolides can be prepared in this way. In addition, this paper describes an experimental protocol for the preparation of solutions

  未活化的内部炔烃的区域选择性羧化可以在大气压下使用二氧化碳进行，使用基于 Sato 型二异丙氧基钛环丙烯化学的简单程序。各种多取代的乙烯基羧酸和丁烯内酯可以通过这种方式制备。此外，本文还介绍了制备（η2-环戊烯）二异丙氧基钛溶液的实验方案。该复合物还与二氧化碳反应，并介导苯乙酮的频哪醇偶联。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• A convenient titanium-mediated intermolecular alkyne–carbonate coupling reaction
  作者：Andrzej Wolan、Frédéric Cadoret、Yvan Six

  DOI：10.1016/j.tet.2009.07.015

  日期：2009.9

  A direct diastereoselective titanium-mediated intermolecular coupling of internal alkynes with dialkyl carbonates under Kulinkovich-type reaction conditions is presented. The influence of the structures of the coupling partners on the yields and regioselectivities of this transformation is described. (C) 2009 Elsevier Ltd. All rights reserved.
• Acylpalladation of Internal Alkynes and Palladium-Catalyzed Carbonylation of (Z)-.beta.-Iodoenones and Related Derivatives Producing .gamma.-Lactones and .gamma.-Lactams
  作者：Christophe Coperet、Takumichi Sugihara、Guangzhong Wu、Izumi Shimoyama、Ei-ichi Negishi

  DOI：10.1021/ja00117a011

  日期：1995.3

  The reaction of either an internal alkyne-organic halide mixture or (Z)-beta-iodoenones with CO in the presence of a Pd-phosphine catalyst, e.g., Cl2Pd(PPh(3))2, can give one of the three discrete types of compounds as the major products depending on the substrate structure and the reaction conditions. Those substrates which are convertible to (Z)-gamma-oxo-alpha,beta-unsaturated acylpalladium derivatives lacking delta-H atoms are converted to the corresponding 2-butenolides (13) in the presence of water, which serves as a H donor. Carbon monoxide most likely is the source of two electrons. Either in the absence of water (or any other suitable H source) or in the presence of some factors disfavoring the butenolide formation, the same reaction gives the corresponding dimeric product (16). Even in cases where there is an alpha-H atom in the alpha-substitutent, 1,4-elimination products (11), reported to be the major products in a related Pd-catalyzed reaction of terminal alkyne-aryl iodide mixtures with CO, were not detected. In sharp contrast, those substrates which can give rise to (Z)-gamma-oxo-alpha, beta-unsaturated acylpalladium derivatives containing delta-H atoms give, under comparable reaction conditions, enol lactones (12), i.e., (Z)-3-alkylidene-2-butenolides, contaminated with only very minor amounts of 22 even in cases where an excess (4 equiv) of water was present. The required (Z)-beta-iodoenones can be readily prepared in one pot via ZrCp(2)-promoted cyclization of alkynes with nitriles. The ready availability of the starting compounds and the high Z stereoselectivity make the overall sequence an attractive synthetic route to 12. The courses of the Pd-catalyzed carbonylation reactions of (Z)-beta-iodo-alpha,beta-unsaturated imines 23 closely parallel the reactions of enones and produce the corresponding lactams, i.e., 24 and 25.