4-hydroxy-1-(p-tolyl)butan-1-one | 113344-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-1-(p-tolyl)butan-1-one
• 英文别名: 4-hydroxy-1-(4’-methylphenyl)butan-1-one；4-Hydroxy-1-(4-methylphenyl)butan-1-one
• CAS: 113344-48-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: UPNRGDJOTNBPLV-UHFFFAOYSA-N

物化性质

• 熔点：
  42-44 °C
• 沸点：
  332.7±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)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1-(p-tolyl)butan-1-one 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-oxo-4-(p-tolyl)butanal
  参考文献：
  名称：

  Sequential multicomponent catalytic synthesis of pyrrole-3-carboxaldehydes: evaluation of antibacterial and antifungal activities along with docking studies

  摘要：

  开发了一种顺序多组分方法，用于合成高度取代的N-芳基吡咯-3-甲醛，并针对细菌菌株进行抗菌和抗真菌活性测试。

  DOI：

  10.1039/d0nj03575k
• 作为产物：
  描述：

  1-(p-tolyl)cyclobutan-1-ol 在 碘苯二乙酸 、 水 作用下， 以 六氟异丙醇 为溶剂， 反应 0.25h， 以90%的产率得到4-hydroxy-1-(p-tolyl)butan-1-one
  参考文献：
  名称：

  Phenyliodine diacetate-mediated oxidative cleavage of cyclobutanols leading to γ-hydroxy ketones

  摘要：

  Oxidative cleavage of cyclobutanols using PIDA, which leads to efficient entry of gamma-hydroxy ketones, is described. When using 2-substituted cyclobutanols, gamma-substituted gamma-hydroxy ketones are obtained through regioselective C-C bond cleavage. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.032

文献信息

• Regioselective Synthesis of 4-Substituted-1-Aryl-1-butanones Using a Sonogashira-Hydration Strategy: Copper-Free Palladium-Catalyzed Reaction of Terminal Alkynes with Aryl Bromides
  作者：Manojit Pal、Karuppasamy Parasuraman、Shalabh Gupta、Koteswar Rao Yeleswarapu

  DOI：10.1055/s-2002-35587

  日期：——

  4-substituted-l-aryl-1-butanones through copper-free Sonogashira reaction of aryl bromides with terminal alkynes in DMF under inert atmosphere, followed by the treatment with acid in the presence of oxygen. A variety of aryl bromides was reacted with 3-butyn-1-ol according to this procedure to give the expected compounds in good yield. The mechanism of the reaction and applications of the methodology are discussed

  已开发出一种简单的一锅法，通过芳基溴化物与末端炔烃在惰性气氛下在 DMF 中的无铜 Sonogashira 反应合成 4-取代-1-芳基-1-丁酮，然后在 DMF 中用酸处理。氧气的存在。根据该程序，多种芳基溴化物与3-丁炔-1-醇反应，以良好的产率得到预期的化合物。讨论了反应机理和方法学的应用。
• Cyclic ether synthesis from diols using trimethyl phosphate
  作者：Shota Asai、Maho Kato、Yasunari Monguchi、Hironao Sajiki、Yoshinari Sawama

  DOI：10.1039/c7cc01514c

  日期：——

  Cyclic ethers have been effectively synthesized via the intramolecular cyclization of diols using trimethyl phosphate and NaH. The present cyclization could proceed at room temperature to produce 5–7 membered cyclic ethers in good to excellent yields. Substrates possessing a chiral secondary hydroxy group were transformed into the corresponding chiral cyclic ethers along with the retention of their

  通过使用磷酸三甲酯和NaH通过二醇的分子内环化，已经有效地合成了环醚。目前的环化反应可以在室温下进行，从而以优异的产率生产5-7元环醚。具有手性仲羟基的底物连同其立体化学的保留一起被转化成相应的手性环醚。
• 2,2-Dimethyl-1,3-oxathiane 3,3-Dioxide: A γ-Hydroxypropyl Anion Equivalent
  作者：Kaoru Fuji、Yoshihide Usami、Yoshimitsu Kiryu、Manabu Node

  DOI：10.1055/s-1992-26246

  日期：——

  The reaction of 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide with various electrophiles is presented. Acylation of the anion provided labile 4-acyl-2, 2-dimethyl-1,3-oxathiane 3,3-dioxides which underwent desulfonation with silica gel to produce γ-hydroxy ketones with three carbon unit elongation. Thus, 4-lithio-2,2-dimethyl-1,3-oxathiane 3,3-dioxide was shown to be a useful synthetic equivalent of a γ-hydroxypropyl anion. Methyl esters proved to be the best acylating agents in this reaction. Synthetic utility of this carbon chain elongation was illustrated by the syntheses of dl-lanceol and dl-dihydrojasmone.

  4-锂-2,2-二甲基-1,3-噁硫烷-3,3-二氧化物与各种电亲体的反应结果被呈现。对阴离子的酰化提供了不稳定的4-酰基-2,2-二甲基-1,3-噁硫烷-3,3-二氧化物，这些化合物与硅胶脱磺反应，生成了具有三个碳单位延长的γ-羟基酮。因此，4-锂-2,2-二甲基-1,3-噁硫烷-3,3-二氧化物被证明是一种有用的γ-羟基丙基阴离子的合成等价物。甲基酯在这个反应中被证明是最佳的酰化试剂。这种碳链延长的合成实用性通过合成dl-兰索尔和dl-二氢茉莉酮得到了说明。
• Catalytic Asymmetric Intramolecular Homologation of Ketones with α-Diazoesters: Synthesis of Cyclic α-Aryl/Alkyl β-Ketoesters
  作者：Wei Li、Fei Tan、Xiaoyu Hao、Gang Wang、Yu Tang、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1002/anie.201409572

  日期：2015.1.26

  A catalytic asymmetric intramolecular homologation of simple ketones with α‐diazoesters was firstly accomplished with a chiral N,N′‐dioxide–Sc(OTf)3 complex. This method provides an efficient access to chiral cyclic α‐aryl/alkyl β‐ketoesters containing an all‐carbon quaternary stereocenter. Under mild conditions, a variety of aryl‐ and alkyl‐substituted ketone groups reacted with α‐diazoester groups

  首先用手性N，N'-二氧化物-Sc（OTf）3配合物完成了简单的酮与α-重氮化合物的催化不对称分子内同源性。这种方法可以有效地获得含有全碳季立体中心的手性环状α-芳基/烷基β-酮酸酯。在温和的条件下，各种芳基和烷基取代的酮基通过分子内加成/重排过程与α-重氮酸酯基团平稳反应，从而以高收率和对映体过量生成β-酮酸酯。
• A new method for the preparation of γ-hydroxy ketones: a formal total synthesis of (±)-lanceol
  作者：Kaoru Fuji、Manabu Node、Yoshihide Usami、Yoshimitsu Kiryu

  DOI：10.1039/c39870000449

  日期：——

  The reaction of methyl esters with 2,2-dimethyl-4-lithio-1,3-oxathiane 3,3-dioxide followed by treatment with silica gel affords γ-hydroxy ketones.

  甲酯与2,2-二甲基-4-硫代-1,3-氧杂蒽3,3-二氧化物反应，然后用硅胶处理，得到γ-羟基酮。