1,3-二羟基-3-苯基丁烷-2-酮 | 102654-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3-二羟基-3-苯基丁烷-2-酮
• 英文名称: 1,3-dihydroxy-3-phenylbutan-2-one
• CAS: 102654-28-4
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: PCDCFYFLYUINMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯基-3-丁炔-2-醇 在 碘苯 、 三氟乙酸酐 作用下， 以 水 、 乙腈 为溶剂， 反应 28.0h， 以76%的产率得到1,3-二羟基-3-苯基丁烷-2-酮
  参考文献：
  名称：

  Iodobenzene-catalyzed synthesis of α,α′-dihydroxy ketones: In situ generation of [bis(trifluoroacetoxy)iodo]benzene

  摘要：

  Exposure of ethynyl carbinols to oxone/(CF3CO)(2)O in the presence of a catalytic amount of iodobenzene afforded ,-dihydroxy ketones in good yield, which are common structural motifs in natural products and biologically active compounds. Compared with traditional methods, this method is more convenient and avoids using stoichiometric amounts of hypervalent iodine reagents.

  DOI：

  10.1080/00397911.2015.1121279

文献信息

• Synthesis of α-Acyloxy-α′-hydroxy Ketones via Cyclic Carbonate Intermediates Generated from Tertiary Bromopropargylic Alcohols and Cs₂ CO₃
  作者：Olesya A. Shemyakina、Ol'ga G. Volostnykh、Anton V. Stepanov、Igor' A. Ushakov

  DOI：10.1002/ejoc.201901226

  日期：2019.11.14

  The Cs2CO3‐promoted synthesis of α‐acyloxy‐α′‐hydroxy ketones is reported, in which tertiary bromopropargylic alcohols undergo hydration/acylation with carboxylic acids via in situ formation of cyclic carbonates.

  据报道，Cs 2 CO 3促进了α-酰氧基-α'-羟基酮的合成，其中叔溴炔丙醇通过原位形成环状碳酸酯与羧酸水合/酰化。
• Cortical Steroid Analogs. III. Further Synthetic and Structure Studies on Acyclic Dihydroxyacetones Derived from 2,3-Butanedione. 1,3-Dihydroxy-3-phenyl-2-butanone¹
  作者：GARDNER W. STACY、RICHARD A. MIKULEC、C. RICHARD BRESSON、LAURENCE D. STARR

  DOI：10.1021/jo01090a016

  日期：1959.8
• Iodobenzene-catalyzed synthesis of <font>α</font>,<font>α</font>′-dihydroxy ketones: In situ generation of [bis(trifluoroacetoxy)iodo]benzene
  作者：Chengqun Chen、Minghua You、Hong Chen

  DOI：10.1080/00397911.2015.1121279

  日期：2016.1.2

  Exposure of ethynyl carbinols to oxone/(CF3CO)(2)O in the presence of a catalytic amount of iodobenzene afforded ,-dihydroxy ketones in good yield, which are common structural motifs in natural products and biologically active compounds. Compared with traditional methods, this method is more convenient and avoids using stoichiometric amounts of hypervalent iodine reagents.