1,3-diphenyl-2-(1-phenyl-allyl)-propane-1,3-dione | 422270-75-5

• 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: 1,3-diphenyl-2-(1-phenyl-allyl)-propane-1,3-dione
• 英文别名: 1,3-Diphenyl-2-(1-phenylprop-2-enyl)propane-1,3-dione
• CAS: 422270-75-5
• 化学式: C₂₄H₂₀O₂
• 分子量: 340.422
• InChiKey: PERIRQMUJIKFSS-UHFFFAOYSA-N

物化性质

• 沸点：
  506.9±50.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-diphenyl-2-(1-phenyl-allyl)-propane-1,3-dione 在 碘 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 cis-3-benzoyl-5-iodomethyl-2,4-diphenyl-4,5-dihydrofuran 、 trans-3-benzoyl-5-iodomethyl-2,4-diphenyl-4,5-dihydrofuran
  参考文献：
  名称：

  Diastereoselective synthesis of 4,5-dihydrofurans by iodoenolcyclisation of 2-allyl-1,3-dicarbonyl compounds

  摘要：

  A study of the stereochemical aspects of I-2-induced cyclisation of 2-alkenyl-1,3-dicarbonyl compounds reveals that the iodoenolcyclisation is strictly dependent on the dicarbonyl species and the substituents in the allylic position. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01064-5
• 作为产物：
  描述：

  二苯甲酰基甲烷 在 哌啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 5.0h， 生成 1,3-diphenyl-2-(1-phenyl-allyl)-propane-1,3-dione
  参考文献：
  名称：

  A new route to 2-alkenyl-1,3-dicarbonyl compounds, intermediates in the synthesis of dihydrofurans

  摘要：

  A two step synthetic strategy for obtaining 2-alkenyl-1,3-dicarbonyl compounds from the corresponding 1,3-dicarbonyl compounds is reported. The method is based on a Knoevenagel condensation and a Michael addition using a high order organocuprate procedure, and proves to be of general value, Obtained compounds are useful starting materials for the synthesis of furan derivatives, (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01173-5

文献信息

• Gold(I)/Chiral <i>N</i> , <i>N′</i> ‐Dioxide–Nickel(II) Relay Catalysis for Asymmetric Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement
  作者：Jun Li、Lili Lin、Bowen Hu、Pengfei Zhou、Tianyu Huang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/anie.201611214

  日期：2017.1.16

  efficient asymmetric cascade reaction between alkynyl esters and allylic alcohols has been realized. Key to success was the combination of a hydroalkoxylation reaction catalyzed by a π‐acidic gold(I) complex with a Claisen rearrangement catalyzed by a chiral Lewis acidic N,N′‐dioxide–nickel(II) complex. A range of acyclic α‐allyl β‐keto esters were synthesized in high yields (up to 99 %) with good

  已经实现了炔基酯和烯丙基醇之间的高效不对称级联反应。成功的关键是由π-酸性金（I）配合物催化的加氢烷氧基化反应与由手性Lewis酸性N，N'-二氧化物-镍（II）配合物催化的Claisen重排的结合。在温和的反应条件下，以高收率（高达99：3）和良好的非对映选择性（高达97：3）和出色的对映选择性（高达99％ee）合成了一系列无环α-烯丙基β-酮酸酯 。这些产品可以轻松转化为光学活性的β-羟基酯，β-羟基酸或1,3-二醇。
• Regioselective allylic alkylation and etherification catalyzed by in situ generated N-heterocyclic carbene ruthenium complexes
  作者：Nevin Gürbüz、Ismail Özdemir、Bekir Çetinkaya、Jean-Luc Renaud、Bernard Demerseman、Christian Bruneau

  DOI：10.1016/j.tetlet.2005.11.051

  日期：2006.1

  chlorides by carbon nucleophiles and phenols, respectively. After generation of diaminocarbene species upon deprotonation by tBuOK, their association with [Cp*Ru(MeCN)3]PF6 induces a very high regioselectivity in favor of the branched isomers when cinnamyl derivatives are used as starting substrates. They also provide good regioselectivities for the allylation of phenols by unsymmetrical aliphatic allylic

  卤代苯并咪唑鎓盐首次用作配体前体，分别被碳亲核试剂和苯酚钌催化的烯丙基碳酸盐和氯化物取代。在通过t BuOK去质子化后生成二氨基卡宾物质后，当使用肉桂基衍生物作为起始底物时，它们与[Cp * Ru（MeCN）3 ] PF 6的缔合引起非常高的区域选择性，有利于支链异构体。它们还为苯酚通过不对称脂族烯丙基底物（如3-氯-4-苯基丁-1-烯）的烯丙基化提供了良好的区域选择性，因此可以直接获得新的烯丙基苯基醚。
• New 1,2,4,5-tetrakis-(N-imidazoliniummethyl)benzene and 1,2,4,5-tetrakis-(N-benzimidazoliummethyl)benzene salts as N-heterocyclic tetracarbene precursors: synthesis and involvement in ruthenium-catalyzed allylation reactions
  作者：Nevin Gürbüz、Serpil Demir、Ismail Özdemir、Bekir Cetinkaya、Christian Bruneau

  DOI：10.1016/j.tet.2009.12.004

  日期：2010.2

  New tetraimidazolinium and tetrabenzimidazolium salts have been prepared. Upon reaction with tBuOK, they generate carbene ligands, which were associated in situ to [RuCp*(MeCN)3]PF6 to produce new ruthenium catalysts that are active for the substitution of allylic substrates by amines, phenols, and carbonucleophiles. The influence of the N-heterocyclic core as well as that of the N-substitutents at

  已经制备了新的四咪唑啉鎓盐和四苯并咪唑鎓盐。与t BuOK反应后，它们生成卡宾配体，该卡宾配体与[RuCp *（MeCN）3 ] PF 6原位缔合，从而生成新的钌催化剂，该催化剂对用胺，酚和碳亲核试剂取代烯丙基底物具有活性。已经研究了N-杂环核心以及盐外围的N-取代基对反应性和区域选择性的影响。
• Ruthenium(<scp>ii</scp>)-catalysed direct synthesis of mono-allylation products of 1,3-diketones from cinnamyl alcohols
  作者：Rajesh K. Jena、Mahesh Samanta、Mohan C. Sau、Sonali Panda、Braja N. Patra、Manish Bhattacharjee

  DOI：10.1039/d2nj01650h

  日期：——

  synthesized and structurally characterized. It crystallizes in the orthorhombic non-centrosymmetric space group P212121 and undergoes auto-resolution. The complex is an efficient catalyst for direct carbon–carbon bond-formation reactions using cinnamyl alcohols to produce enantio- and regioselective mono-allylation products of diketones in high yield. A wide range of substrates provides good to excellent

  合成了复合物[Ru( p -cymene)(dppe)Cl]PF 6 ·C 7 H 8并进行了结构表征。它在正交非中心对称空间群P 2 1 2 1 2 1中结晶并经历自动分辨。该配合物是一种有效的催化剂，用于直接碳-碳键形成反应，使用肉桂醇以高收率生产二酮的对映选择性和区域选择性单烯丙基化产物。广泛的基材提供了良好的产量。吡咯烷和乙酸添加剂的使用增加了选择性并防止了不需要的副产物。
• Arylboronic Acid Catalyzed <i>C</i>-Alkylation and Allylation Reactions Using Benzylic Alcohols
  作者：Susana Estopiñá-Durán、Euan B. Mclean、Liam J. Donnelly、Bryony M. Hockin、James E. Taylor

  DOI：10.1021/acs.orglett.0c02736

  日期：2020.10.2

  The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C-C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).