2-methyl-3-(benzo[d][1,3]dioxol-5-yl)-1-phenylpropan-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-methyl-3-(benzo[d][1,3]dioxol-5-yl)-1-phenylpropan-1-one
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: JESIULRLKWQVPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  胡椒醇 、 1-苯丙醇 在 potassium tert-butylate 、 (6-OH-bpy)NiCl₂ 作用下， 以 甲苯 为溶剂， 以47 %的产率得到2-methyl-3-(benzo[d][1,3]dioxol-5-yl)-1-phenylpropan-1-one
  参考文献：
  名称：

  镍催化醇的化学发散偶联：获得 α,α-二取代酮和 α-取代查耳酮的有效途径

  摘要：

  化学发散镍催化方法在 KO t Bu 存在下通过借氢 (BH) 策略从芳基取代的仲醇和苯甲醇提供α , α-二取代酮，而仅α-取代查耳酮是在 KO t Bu 存在下完成的。通过无受体脱氢偶联 (ADC) 策略实现弱碱 K 2 CO 3 。

  DOI：

  10.1002/chem.202304082

文献信息

• Iron-Catalyzed Tandem Three-Component Alkylation: Access to α-Methylated Substituted Ketones
  作者：Léo Bettoni、Charlotte Seck、Mbaye Diagne Mbaye、Sylvain Gaillard、Jean-Luc Renaud

  DOI：10.1021/acs.orglett.9b00630

  日期：2019.5.3

  The borrowing hydrogen strategy has been applied in the synthesis of α-branched methylated ketones via a tandem three-component reaction catalyzed by a diaminocyclopentadienone iron tricarbonyl complex. Various alkyl and aromatic methyl ketones underwent dialkylation with various primary alcohols and methanol as alkylating agents in mild reaction conditions and good yields. Deuterium labeling experiments

  通过二氨基环戊二烯酮三羰基铁络合物催化的串联三组分反应，借位氢策略已应用于α-支化甲基化酮的合成中。各种烷基和芳族甲基酮在温和的反应条件下以良好的收率与各种伯醇和甲醇作为烷基化剂进行了二烷基化反应。氘标记实验表明，在串联过程中，苯甲醇是氢源。
• Utilization of MeOH as a C1 Building Block in Tandem Three-Component Coupling Reaction
  作者：Kaushik Chakrabarti、Milan Maji、Dibyajyoti Panja、Bhaskar Paul、Sujan Shee、Gourab Kanti Das、Sabuj Kundu

  DOI：10.1021/acs.orglett.7b02105

  日期：2017.9.15

  Ru(II) catalyzed tandem synthesis of α-branched methylated ketones via multicomponent reactions following the hydrogen borrowing process is described. This nonphosphine-based air and moisture stable catalyst efficiently produced various methylated ketones using methanol as a methylating agent. This system was found to be highly effective in three-component coupling between methanol, primary alcohols

  描述了Ru（II）在氢借位过程之后通过多组分反应催化串联合成α-支化甲基化酮。使用甲醇作为甲基化剂，这种基于非膦的空气和水分稳定的催化剂有效地生产了各种甲基化的酮。发现该系统在甲醇，伯醇和甲基酮之间的三组分偶联中非常有效。DFT计算和动力学实验支持了拟议的α-甲基化催化循环。
• One-pot three-component synthesis of α-methylated ketones from secondary and primary aryl alcohols
  作者：Shaikh Samser、Priyabrata Biswal、Omkar Mohapatra、Sanu Siyad Pullarat、Sushanta Kumar Meher、Krishnan Venkatasubbaiah

  DOI：10.1039/d3nj05498e

  日期：——

  One-pot three-component synthesis of α-methylated ketones from secondary and primary alcohols via a triple dehydrogenative method is presented here. This protocol uses a polystyrene-supported catalyst and the catalyst is reused for five runs without any drop in its activity. Detailed mechanistic investigation was carried out with control reactions and deuterium labelling experiments revealed that secondary

  本文介绍了通过三重脱氢方法从仲醇和伯醇一锅三组分合成 α-甲基化酮。该方案使用聚苯乙烯负载的催化剂，并且该催化剂可重复使用五次运行，其活性没有任何下降。通过控制反应和氘标记实验进行了详细的机理研究，表明仲醇和伯醇在 α-甲基化取代酮的一锅合成中充当氢源。
• Nickel‐Catalyzed Chemodivergent Coupling of Alcohols: Efficient Routes to Access α,α‐Disubstituted Ketones and α‐Substituted Chalcones
  作者：Sadhna Bansal、Benudhar Punji

  DOI：10.1002/chem.202304082

  日期：2024.3.12

  The chemodivergent nickel-catalyzed approach provides α,α-disubstituted ketones from aryl-substituted secondary alcohols and benzyl alcohols via the borrowing hydrogen (BH) strategy in the presence of KOtBu, whereas exclusively α-substituted chalcones were accomplished in the presence of mild base K2CO3 through an acceptorless dehydrogenative coupling (ADC) strategy.

  化学发散镍催化方法在 KO t Bu 存在下通过借氢 (BH) 策略从芳基取代的仲醇和苯甲醇提供α , α-二取代酮，而仅α-取代查耳酮是在 KO t Bu 存在下完成的。通过无受体脱氢偶联 (ADC) 策略实现弱碱 K 2 CO 3 。