1-(4-methoxyphenyl)-3-phenylbutan-1-one | 99334-60-8

• 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: 1-(4-methoxyphenyl)-3-phenylbutan-1-one
• CAS: 99334-60-8
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: ZPVPNPYFEUQLTC-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C(Solv: hexane (110-54-3); ethanol (64-17-5))
• 沸点：
  393.6±25.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (+/-)-3-苯基丁酸 在 三氯化铝 、 氯化亚砜 作用下， 生成 1-(4-methoxyphenyl)-3-phenylbutan-1-one
  参考文献：
  名称：

  Boch, R.; Bohne, C; Netto-Ferreira, J. C., Canadian Journal of Chemistry, 1991, vol. 69, # 12, p. 2053 - 2058

  摘要：

  DOI：

文献信息

• Ketone Synthesis by Direct, Orthogonal Chemoselective Hydroacylation of Alkenes with Amides: Use of Alkenes as Surrogates of Alkyl Carbanions
  作者：Hui Geng、Pei‐Qiang Huang

  DOI：10.1002/cjoc.201900252

  日期：2019.8

  and direct transformation of carboxamides are two exciting areas that have attracted considerable attention in recent years. We report herein that secondary amides, the least reactive derivatives of carbonyl compounds, upon activated with triflic anhydride, can serve as effective hydroacylating reagents in partner with alkenes to yield ketones at ambient temperature. The method was applied to the one‐step

  烯烃的直接官能化和羧酰胺的直接转化是近年来令人瞩目的两个令人兴奋的领域。我们在此报道，仲酰胺，即羰基化合物的反应性最低的衍生物，在用三氟甲磺酸酐活化后，可以与烯烃一起作为有效的氢酰化试剂，在环境温度下产生酮。该方法已用于外消旋二氢芳基羟色酮的一步合成。在这种方法中，烯烃用作有机金属试剂的替代物，从而可以进行正交的化学选择性反应。许多烯烃（如camp烯和降冰片烯）的现成性允许一步合成酮，而传统方法则需要几个步骤。
• Catalytic Asymmetric Transfer Hydrogenation of <i>trans</i>-Chalcone Derivatives Using BINOL-derived Boro-phosphates
  作者：Fei Na、Susana S. Lopez、Alice Beauseigneur、Lucas W. Hernandez、Zhuoxin Sun、Jon C. Antilla

  DOI：10.1021/acs.orglett.0c02042

  日期：2020.8.7

  Chiral phosphoric-acid-catalyzed asymmetric reductions of trans-chalcones have been investigated in this work. A BINOL-derived boro-phosphate-catalyzed asymmetric transfer hydrogenation of the carbon–carbon double bond of trans-chalcone derivatives employing borane as a hydride source was realized. This methodology provides a convenient procedure to access chiral dihydrochalone derivatives in high

  在这项工作中，已经研究了手性磷酸催化反式查耳酮的不对称还原。利用硼烷作为氢化物来源，实现了反式查尔酮衍生物的碳-碳双键的BINOL衍生的硼磷酸盐催化的不对称转移氢化。该方法提供了在温和条件下以高收率和高对映选择性获得手性二氢氢醌衍生物的简便方法。
• Effect of InCl 3 on the addition of Grignard reagents to α,β-unsaturated carbonyl compounds
  作者：Brian G. Kelly、Declan G. Gilheany

  DOI：10.1016/s0040-4039(01)02263-8

  日期：2002.1

  Control of 1,2- versus 1,4-addition of organometallic reagents to enones remains a long-standing problem. There is still no satisfactory 1,2-directing agent comparable to the 1,4-directing effect of copper salts. We report that the presence of just 5 mol% indium(III) chloride can significantly alter the amount of 1,2-product formed in these reactions.

  控制有机金属试剂向烯酮的1,2-和1,4-加成仍然是一个长期存在的问题。仍然没有令人满意的与铜盐的1，4-定向作用相当的1，2-定向剂。我们报告说，仅5摩尔％的氯化铟（III）的存在可以显着改变这些反应中形成的1,2-产物的量。
• Iron-Catalyzed α-Alkylation of Ketones with Secondary Alcohols: Access to β-Disubstituted Carbonyl Compounds
  作者：Léo Bettoni、Sylvain Gaillard、Jean-Luc Renaud

  DOI：10.1021/acs.orglett.0c00549

  日期：2020.3.6

  borrowing hydrogen strategy has been applied in the synthesis of β-branched carbonyl compounds. Various secondary benzylic and aliphatic alcohols have been used as alkylating reagents under mild reaction conditions. The ketones have been isolated in good to excellent yield. Deuterium labeling experiments provide evidence that the alcohol is the hydride source in this reaction and that no reversible step or

  铁催化的借位氢策略已用于合成β-支链羰基化合物。在温和的反应条件下，各种仲苄醇和脂族醇已被用作烷基化试剂。酮以良好至极好的收率被分离出来。氘标记实验提供了证据，表明醇是该反应中的氢化物来源，并且在此过程中未发生可逆步骤或氢/氘加扰。
• Rhenium complex-catalyzed coupling reaction of enol acetates with alcohols
  作者：Rui Umeda、Yuuki Takahashi、Yutaka Nishiyama

  DOI：10.1016/j.tetlet.2014.09.054

  日期：2014.10

  The reaction of enol acetates with alcohols in the presence of a catalytic amount of a rhenium complex, such as ReBr(CO)5, produced the corresponding ketones and aldehydes in moderate to good yields. It was suggested that the preparation of an ether, an intermolecular dehydrated product, was the first step of the reaction.

  在催化量的complex络合物例如ReBr（CO）5的存在下，烯醇乙酸酯与醇的反应以中等至良好的产率产生了相应的酮和醛。有人建议，醚（一种分子间脱水产物）的制备是反应的第一步。