6-methyl-1-phenylheptan-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-methyl-1-phenylheptan-3-one
• 英文别名: 6-Methyl-1-phenyl-heptan-3-one
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: OVUNXGJJDPLPJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  6-methyl-1-phenylheptan-3-one 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  通过串联1,5-HAT的远程C（sp3）-H键的亚氨基自由基介导的受控羟烷基化和芳基烯烃的双官能化

  摘要：

  在氧化还原中性条件下，通过C（sp 3）-H官能团形成了可见光介导的酮的γ-羟烷基化反应。该协议依赖于亚胺基引发的1,5-HAT，然后进行烯烃的氧烷基化，其中CC和C-O键是一步构建的。该三组分反应具有温和的条件，宽的底物范围和出色的官能团耐受性，因此可以轻松高效地获得复杂的有价值的酮。

  DOI：

  10.1002/adsc.201801198
• 作为产物：
  描述：

  1-溴代异戊烷 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.08h， 生成 6-methyl-1-phenylheptan-3-one
  参考文献：
  名称：

  Novel Routes to Enol Ethers, Unsymmetrical Ketones, .alpha.-Bromoalkyl Ketones, 1,4-Diketones, 2-Ethoxy-2-cyclopentenones, and .alpha.-Keto Enamines

  摘要：

  Highly regioselective S(N)2' reactions of adducts 6 (readily prepared by reactions of halides with the allyl anion 12 of 11) with Grignard reagents gave enol ethers 13, which were converted (in one-pot reactions from 11) into ketones 14 and alpha-bromoalkyl ketones 15 in good yields. The monoprotected 1,4-diketone derivative 16 (prepared by Michael addition of the allyl anion 12 with methyl vinyl ketone) was converted both into 1,4-diketones 18 and into protected gamma-hydroxyalkyl ketone 20 by selective Grignard reactions, which could be directed either to the carbonyl, or the protected propenoyl, or to both functionalities. The allyl anion 12 with alpha-substituted acetic esters gave alpha-acylated adducts 24, which underwent in situ unfavored endo-trig cyclization upon treatment with NaH and secondary amines, to give 2-ethoxy-2-cyclopentenones 27 and 28 and alpha-keto enamines 25 in good yield. The mechanism for the cyclization is discussed.

  DOI：

  10.1021/jo00128a037

文献信息

• Alcohols for the α-Alkylation of Methyl Ketones and Indirect Aza-Wittig Reaction Promoted by Nickel Nanoparticles
  作者：Francisco Alonso、Paola Riente、Miguel Yus

  DOI：10.1002/ejoc.200800729

  日期：2008.10

  Nickel nanoparticles have been found to activate primary alcohols used for the α-alkylation of ketones or in indirect aza-Wittig reactions. These processes involve hydrogen transfer from the alcohol to the intermediate α,β-unsaturated ketone or imine, respectively. All these reactions are carried out in the absence of any ligand, hydrogen acceptor or base under mild reaction conditions. For the first

  已发现镍纳米粒子可激活用于酮的 α-烷基化或间接 aza-Wittig 反应的伯醇。这些过程分别涉及从醇到中间体 α,β-不饱和酮或亚胺的氢转移。所有这些反应都是在温和的反应条件下在没有任何配体、氢受体或碱的情况下进行的。在这两个反应中，镍首次被用作贵金属基催化剂的潜在替代品。在一些氘化实验的基础上提出了反应机理。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Iminyl Radical-Triggered Intermolecular Distal C(sp³)–H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade
  作者：Yu-Rui Gu、Xin-Hua Duan、Li Chen、Zhi-Yong Ma、Pin Gao、Li-Na Guo

  DOI：10.1021/acs.orglett.8b03865

  日期：2019.2.15

  An efficient iron-catalyzed intermolecular remote C(sp3)–H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety of alkyl ketones and heteroaryls, thus providing a straightforward method for the late-stage functionalization of alkylketones and heteroaryls.

  通过亚胺基引发的1，5-氢原子转移（HAT）级联反应，开发了一种有效的铁催化的烷基酮的分子间远程C（sp 3）-H杂芳基化反应。该方案适用于多种烷基酮和杂芳基，因此为烷基酮和杂芳基的后期官能化提供了一种直接的方法。
• Visible-Light-Promoted Catalytic Ring-Opening Isomerization of 1,2-Disubstituted Cyclopropanols to Linear Ketones
  作者：Marharyta V. Laktsevich-Iskryk、Nastassia A. Varabyeva、Volha V. Kazlova、Vladimir N. Zhabinskii、Vladimir A. Khripach、Alaksiej L. Hurski

  DOI：10.1002/ejoc.202000094

  日期：2020.5.3

  A visible‐light‐promoted acridinium‐catalyzed radical isomerization of 1,2‐disubstituted cyclopropoanols to linear ketones is reported.

  据报道1,2-二取代的环丙醇在可见光促进下的din啶催化的自由基异构化为线性酮。
• Solid-Phase, Multicomponent Reactions of Methyleneaziridines:  Synthesis of 1,3-Disubstituted Propanones
  作者：Jean-François Margathe、Michael Shipman、Stephen C. Smith

  DOI：10.1021/ol051953a

  日期：2005.10.1

  [reaction: see text] Polymer-supported methyleneaziridines undergo ring opening by Grignard reagents under copper catalysis to yield metalloenamines which are alkylated in situ to yield ketimines. Filtration and washing of these Merrifield resin-bound intermediates prior to hydrolysis provides the corresponding 1,3-disubstituted propanones in a high state of purity without recourse to column chromatography

  [反应：参见正文]聚合物负载的亚甲基氮丙啶在铜催化下通过格氏试剂进行开环，生成金属烯胺，将其原位烷基化以生成酮亚胺。在水解之前过滤和洗涤这些与Merrifield树脂结合的中间体，可以提供高纯度的相应1,3-二取代丙烷，而无需借助柱色谱。
• Formation of pyrrolidines by the titanocene(II)-promoted intramolecular reaction of N-[3,3-bis(phenylthio)propyl]anilides
  作者：Takeshi Takeda、Jun Saito、Akira Tsubouchi

  DOI：10.1016/s0040-4039(03)01385-6

  日期：2003.7

  titanium carbene complexes generated by the desulfurization of thioacetals with the titanocene(II) species Cp2Ti[P(OEt)3]2 produced the corresponding enamines. Unusual formation of pyrrolidines was observed when N-[3,3-bis(phenylthio)propyl]anilides were treated with the titanocene(II) reagent.

  乙醛与硫代缩醛与钛茂（II）物种Cp 2 Ti [P（OEt）3 ] 2脱硫生成的钛卡宾配合物反应生成相应的烯胺。当用钛茂（II）试剂处理N- [3,3-双（苯硫基）丙基]苯胺时，观察到吡咯烷的异常形成。