2-methyl-1,3-diphenyl-pent-4-en-1-one

• 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: 2-methyl-1,3-diphenyl-pent-4-en-1-one
• 英文别名: 2-Methyl-1,3-diphenylpent-4-en-1-one
• 化学式: C₁₈H₁₈O
• 分子量: 250.34
• InChiKey: IKYGVDBRRNJWDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  2-methyl-1,3-diphenyl-pent-4-en-1-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (1S,2S,3S)-2-methyl-1,3-diphenyl-pent-4-en-1-ol
  参考文献：
  名称：

  高度区域选择性、非对映选择性和对映选择性 Pd 催化的无环酮烯醇化物与单取代烯丙基底物的烯丙基烷基化

  摘要：

  Pd 催化无环酮与单取代烯丙基底物的不对称烯丙基烷基化反应，使用 1,1'-P,N-二茂铁，H 作为恶唑啉环上的取代基作为配体，得到具有两个手性中心的高产率和高区域-，非对映选择性和对映选择性，支链和线性产物的比例为 98:2，支链产物的反：syn 比例为 7-21:1，反产物的 ee 为 92-99%。

  DOI：

  10.1021/ja071098l
• 作为产物：
  描述：

  1-苯基-2-丙烯-1-醇 在 [Ru(η(5)-C5,κ-P-Cp(P))(CH3CN)2]PF6 作用下， 以 氘代四氢呋喃 为溶剂， 反应 1.92h， 以64%的产率得到苯丙酮
  参考文献：
  名称：

  Redox Isomerization of Allylic Alcohols Catalyzed by Osmium and Ruthenium Complexes Containing a Cyclopentadienyl Ligand with a Pendant Amine or Phosphoramidite Group: X-ray Structure of an η³-1-Hydroxyallyl-Metal-Hydride Intermediate

  摘要：

  Complexes [MCl2(eta(6)-p-cymene)](2) (M = Os (1a), Ru (1b)) react with Li(C5H4CH2CH2NHMe) (LiCpN) and KPF6 to give the sandwich derivatives [M(eta(5)-Cp-N)(eta(6)-p-cymene)]PF6 (M = Os (2a), Ru (2b)). Treatment of 2a and 2b with (2,2'-biphenol)PCI leads to [M(eta(5)-Cp-P)(eta(6)-p-cymene)]PF6 (M = Os (3a), Ru (3b); CpP = C5H4CH2CH2N(Me)P(2,2'-biphenol)). The photolysis of 2a, 2b, 3a, and 3h in acetonitrile produces the release of the p-cymene group and the coordination of the cyclopentadienyl pendant substituent to the metal center to afford [M(eta(5)-C-5,kappa-N-CpN)(CH3CN)(2)]PF6 (M = Os (4a), Ru (4b)) and [M(eta(5)-C-5,kappa-P-Cp-P)(CH3CN)(2)]PF6 (M = Os (5a), Ru (5b)). Complex 4a, which has been characterized by X-ray diffraction analysis, is a more efficient catalyst precursor than 4b for the redox isomerization of primary allylic alcohols, while the latter is more efficient than the former for the redox isomerization of secondary allylic alcohols. From the catalytic solutions containing 4a and 2-methyl-2-propen-1-ol, the eta 3-1-hydroxyallyl complex [OsH(eta(5)-C-5,kappa-N-CPN){eta(3)-CH2C(CH3)CHOH}]PF6 (6) has been crystallized and characterized by spectroscopic methods and X-ray diffraction analysis. The structure shows a N-H center dot center dot center dot O hydrogen bond (2.22 A) between the NH-hydrogen atom of the coordinated pendant amine group and the oxygen atom of the hydroxy substituent of the allyl ligand.

  DOI：

  10.1021/om100126t

文献信息

• Boron trifluoride-catalyzed reaction of alkyl fluoride with silyl enolate, allylsilane, and hydrosilane
  作者：Koji Hirano、Kazuya Fujita、Hideki Yorimitsu、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1016/j.tetlet.2004.01.145

  日期：2004.3

  Alkylation of silyl enolates with tert-alkyl or allylic fluorides proceeds smoothly in the presence of a catalytic amount of boron trifluoride to afford the corresponding carbonyl compounds. Allylation and reduction of alkyl fluorides with allylsilane and hydrosilane, respectively, occur under BF3 catalysis.

  在催化量的三氟化硼的存在下，用叔烷基或烯丙基氟化物进行烯基甲酸酯的烷基化反应进行得很顺利，从而得到相应的羰基化合物。在BF 3催化下，烷基氟与烯丙基硅烷和氢硅烷的烷基化和还原反应分别发生。
• General and Mild Ni⁰-Catalyzed α-Arylation of Ketones Using Aryl Chlorides
  作者：José A. Fernández-Salas、Enrico Marelli、David B. Cordes、Alexandra M. Z. Slawin、Steven P. Nolan

  DOI：10.1002/chem.201406457

  日期：2015.3.2

  A general methodology for the α‐arylation of ketones using a nickel catalyst has been developed. The new well‐defined [Ni(IPr*)(cin)Cl] (1 c) pre‐catalyst showed great efficiency for this transformation, allowing the coupling of a wide range of ketones, including acetophenone derivatives, with various functionalised aryl chlorides. This cinnamyl‐based Ni–N‐heterocyclic carbene (NHC) complex has demonstrated

  已经开发了使用镍催化剂对酮进行α-芳基化的一般方法。定义明确的新型[Ni（IPr *）（cin）Cl]（1 c）预催化剂显示出极高的转化效率，使各种酮（包括苯乙酮衍生物）与各种官能化的芳基氯化物偶合。这种基于肉桂基的Ni-N-杂环卡宾（NHC）配合物表现出与以前报道的NHC-Ni催化剂不同的行为。初步的机理研究表明，Ni 0 / Ni II催化循环起作用。
• 2-Allylisourea as an Effective Agent for Direct α-Allylation of Ketone and Aldehyde Assisted by Palladium(0) under Neutral Conditions
  作者：Yoshio Inoue、Masanori Toyofuku、Masaaki Taguchi、Shin-ichi Okada、Harukichi Hashimoto

  DOI：10.1246/bcsj.59.885

  日期：1986.3

  Direct α-allylation of a variety of ketones and aldehydes with 2-allylisourea took place in the presence of a catalytic amount of a palladium(0) complex under neutral and mild conditions. Scope and limitations of this novel method have been investigated.

  在催化量的钯(0)配合物存在下，多种酮和醛与2-烯丙基异脲在中性和温和条件下直接进行α-烯丙基化反应。本新型方法的应用范围和局限性已得到研究。
• INOUE, YOSHIO;TOYOFUKU, MASANORI;TAGUCHI, MASAAKI;OKADA, SHIN-ICHI;HASHIM+, BULL. CHEM. SOC. JAP., 1986, 59, N 3, 885-891
  作者：INOUE, YOSHIO、TOYOFUKU, MASANORI、TAGUCHI, MASAAKI、OKADA, SHIN-ICHI、HASHIM+

  DOI：——

  日期：——
• Highly Regio-, Diastereo-, and Enantioselective Pd-Catalyzed Allylic Alkylation of Acyclic Ketone Enolates with Monosubstituted Allyl Substrates
  作者：Wen-Hua Zheng、Bao-Hui Zheng、Yan Zhang、Xue-Long Hou

  DOI：10.1021/ja071098l

  日期：2007.6.1

  Pd-catalyzed asymmetric allylic alkylation reactions of acyclic ketones with monosubstituted allyl substrates using 1,1‘-P,N-ferrocene with H as substituent on the oxazoline ring as ligand gave products having two chiral centers with high yields and with high regio-, diastereo-, and enantioselectivities, with the ratio of branched and linear products being 98:2, anti:syn ratio for branched products

  Pd 催化无环酮与单取代烯丙基底物的不对称烯丙基烷基化反应，使用 1,1'-P,N-二茂铁，H 作为恶唑啉环上的取代基作为配体，得到具有两个手性中心的高产率和高区域-，非对映选择性和对映选择性，支链和线性产物的比例为 98:2，支链产物的反：syn 比例为 7-21:1，反产物的 ee 为 92-99%。