(E)-2-benzylidene-4-(p-tolyl)but-3-ynal | 1311273-06-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (E)-2-benzylidene-4-(p-tolyl)but-3-ynal
• 英文别名: (2E)-2-benzylidene-4-(4-methylphenyl)but-3-ynal
• CAS: 1311273-06-9
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: WMARGSKZFBAYJP-QGOAFFKASA-N

物化性质

• 沸点：
  417.1±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-benzylidene-4-(p-tolyl)but-3-ynal 在 正丁基锂 、 三苯基膦氯金 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (3E)-4-((E)-3-benzylidene-2-phenyl-5-(p-tolyl)cyclopenta-1,4-dienyl)but-3-en-2-one
  参考文献：
  名称：

  Gold-Catalyzed Approach to Multisubstituted Fulvenes via Cycloisomerization of Furan/Ynes

  摘要：

  A new approach to functionalized fulvenes with an enone or enal moiety has been developed through gold-catalyzed intramolecular cycloisomerization of furan/ynes with a two-carbon tether in between the furan and the triple bond. The reaction proceeds with complete regioselectivity via a 6-endo-cyclization and high stereoselectivity. Moreover, the E- or Z-stereochemistry of the double bond in fulvene products can be easily controlled by performing the reaction in different solvents.

  DOI：

  10.1021/jo2004023
• 作为产物：
  描述：

  肉桂醛 在 bis(diphenylphosphino)palladium(II)dichloride 、 溴 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 生成 (E)-2-benzylidene-4-(p-tolyl)but-3-ynal
  参考文献：
  名称：

  铜催化环状从磺酰肼和1,3-烯炔直接合成苯并[ f ]吲唑

  摘要：

  提出了一种在温和条件下通过磺酰肼与1,3-烯炔的铜催化级联反应直接合成苯并[ f ]吲唑的新颖有效策略。此方法可在一锅中形成两个C–N键和一个C–C键，从而以中等至良好的收率提供了一系列苯并[ f ]吲唑，并具有良好的官能团耐受性和显着的区域选择性。

  DOI：

  10.1021/acs.orglett.8b03564

文献信息

• Direct Synthesis of Benzo[<i>f</i>]indazoles from Sulfonyl Hydrazines and 1,3-Enynes by Copper-Catalyzed Annulation
  作者：Biao Yao、Tao Miao、Pinhua Li、Lei Wang

  DOI：10.1021/acs.orglett.8b03564

  日期：2019.1.4

  A novel and efficient strategy for the direct synthesis of benzo[f]indazoles via copper-catalyzed cascade reaction of sulfonyl hydrazides with 1,3-enynes under mild conditions has been developed. This method achieves the formation of two C–N bonds and one C–C bond in one pot, providing a series of benzo[f]indazoles in moderate to good yields with good functional group tolerance and remarkable regioselectivity

  提出了一种在温和条件下通过磺酰肼与1,3-烯炔的铜催化级联反应直接合成苯并[ f ]吲唑的新颖有效策略。此方法可在一锅中形成两个C–N键和一个C–C键，从而以中等至良好的收率提供了一系列苯并[ f ]吲唑，并具有良好的官能团耐受性和显着的区域选择性。
• Synthesis of 2-Tetrazolyl-Substituted 3-Acylpyrroles via a Sequential Ugi-Azide/Ag-Catalyzed Oxidative Cycloisomerization Reaction
  作者：Han-Han Kong、Hong-Ling Pan、Ming-Wu Ding

  DOI：10.1021/acs.joc.8b01984

  日期：2018.10.19

  cascade cycloisomerization/aerobic oxidation reaction of a Ugi-azide adduct for the preparation of 3-acylpyrroles using molecular oxygen as the terminal oxidant has been developed. A series of 2-tetrazolyl-substituted 3-acylpyrroles were obtained in 62–89% yields from readily available enynals 1, primary amines 2, isocyanides 3, and trimethylsilyl azide 4 in the presence of a catalytic amount of AgNO3 and

  已经开发了一种新的有效的Ag催化的Ugi-叠氮化物加合物的Ag催化的级联环异构化/好氧氧化反应，用于使用分子氧作为末端氧化剂制备3-酰基吡咯。在催化量的AgNO 3和DMAP的存在下，在催化量的条件下，从容易获得的烯类1，伯胺2，异氰化物3和三甲基甲硅烷基叠氮化物4中以62-89％的产率获得了一系列2-四唑基取代的3-酰基吡咯。O 2气氛。
• Efficient AgOTf or Ph3PAuCl–AgSbF6 catalyzed cyclization of 1-hydroxy-2-alkynylallylphosphonates/2-alkynylallyl alcohols to 2-furylphosphonates/2,3,5-trisubstituted furans
  作者：Ramesh Kotikalapudi、K.C. Kumara Swamy

  DOI：10.1016/j.tetlet.2012.04.060

  日期：2012.7

  The reaction of 1-hydroxy-2-alkynylallylphosphonates, synthesized by the addition of the corresponding phosphites to 2-alkynylcinnamaldehydes, under AgOTf or Ph3PAuCl-AgSbF6 catalyzed cycloisomerization afforded 2-furylphosphonates in good to excellent yields. These cyclization reactions were compared with those of 2-alkynylallyl alcohols that led to multisubstituted furans. (C) 2012 Published by Elsevier Ltd.
• Gold-Catalyzed Approach to Multisubstituted Fulvenes via Cycloisomerization of Furan/Ynes
  作者：Yifeng Chen、Yuanhong Liu

  DOI：10.1021/jo2004023

  日期：2011.7.1

  A new approach to functionalized fulvenes with an enone or enal moiety has been developed through gold-catalyzed intramolecular cycloisomerization of furan/ynes with a two-carbon tether in between the furan and the triple bond. The reaction proceeds with complete regioselectivity via a 6-endo-cyclization and high stereoselectivity. Moreover, the E- or Z-stereochemistry of the double bond in fulvene products can be easily controlled by performing the reaction in different solvents.
• NHC-Catalyzed Chemoselective Reactions of Enals and Cyclopropylcarbaldehydes for Access to Chiral Dihydropyranone Derivatives
  作者：Yingling Nong、Chen Pang、Kunpeng Teng、Sheng Zhang、Qian Liu

  DOI：10.1021/acs.joc.3c01171

  日期：2023.10.6

  An N-heterocyclic carbene (NHC)-catalyzed chemoselective activation reaction of 1-cyclopropylcarbaldehydes and α-alkynyl enals is reported. NHC selectively catalyzes 1-cyclopropylaldehydes, followed by a [2 + 4] cycloaddition reaction with α-alkynyl enals. The target dihydropyranone derivatives bearing different substituents and substitution patterns can be obtained in good to excellent yields with

  报道了N-杂环卡宾(NHC) 催化的 1-环丙基甲醛和 α-炔基烯醛的化学选择性活化反应。NHC 选择性催化 1-环丙醛，然后与 α-炔基烯醛发生 [2 + 4] 环加成反应。在温和条件下，可以以良好至优异的产率获得带有不同取代基和取代模式的目标二氢吡喃酮衍生物，并具有优异的对映和非对映选择性。