syn-4-hydroxy-4-phenyl-3-(phenylmethyl)-2-butanone | 132490-27-8

• 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: syn-4-hydroxy-4-phenyl-3-(phenylmethyl)-2-butanone
• 英文别名: PhCH(OH)CH(CH2Ph)COMe；(3S,4S)-3-benzyl-4-hydroxy-4-phenylbutan-2-one
• CAS: 132490-27-8
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: PMTKSPUJMQYWGB-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  {(-)-isopinocampheyl}2(OC(CH3)CHCH2C6H5)borane 、 苯甲醛 在 水 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到syn-4-hydroxy-4-phenyl-3-(phenylmethyl)-2-butanone
  参考文献：
  名称：

  通过（E）-α，β-不饱和酮的1,4加氢硼化制得（Z）-乙烯基氧基硼烷的新方法。合成合成羟醛

  摘要：

  （Z）-乙烯基氧基硼烷是通过在20°C下于四氢呋喃，CH 2 Cl 2或CHCl 3中将无环二取代的（E）-α，β-不饱和酮与二环己基硼烷或二异樟脑环硼烷进行1,4-氢硼化而制得的; 用醛处理加氢硼化混合物可使用后者的硼烷以高收率和极佳的对映体过量合成纯的合成醇醛。

  DOI：

  10.1039/c39900001680

文献信息

• Tandem One-Pot Wittig/Reductive Aldol Reactions in which the Waste from One Process Catalyzes a Subsequent Reaction
  作者：Jinni Lu、Patrick H. Toy

  DOI：10.1002/asia.201100296

  日期：2011.9.5

  Putting waste to work: Tandem one‐pot Wittig/reductive aldol reactions have been performed in which the byproduct of the Wittig reaction, Ph3PO, catalyzes the reductive aldol reaction. This methodology is versatile and allows for three different building blocks to be combined in a simple, one‐pot procedure.

  废物处理：已经进行了串联的一锅式Wittig /还原性羟醛反应，其中Wittig反应的副产物Ph 3 PO催化了还原性羟醛反应。这种方法学用途广泛，可以通过简单的一锅法将三个不同的构建基块组合在一起。
• A NEW METHOD FOR THE REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALDOLS FROM α-BROMOKETONE AND CARBONYL COMPOUNDS BY USING METALLIC TIN
  作者：Taira Harada、Teruaki Mukaiyama

  DOI：10.1246/cl.1982.467

  日期：1982.4.5

  Tin(II) enolates, generated in situ by the oxidative addition of α-bromoketones to metallic tin, react with a variety of carbonyl compounds under mild conditions to give the corresponding aldols in good yields. In the case of reactions of the enolate resulted from α-substituted α-bromoketone with aldehydes, remarkably high erythro-selectivities are attained.

  锡 (II) 烯醇化物通过 α-溴酮与金属锡的氧化加成原位生成，在温和条件下与各种羰基化合物反应，以良好的收率得到相应的醛醇。在由 α-取代的 α-溴酮与醛产生的烯醇反应的情况下，获得了非常高的赤型选择性。
• Copper-Catalyzed Umpolung Reactivity of Propargylic Carbonates in the Presence of Diboronates: One Stone Four Birds
  作者：Wennan Dong、Zhifei Zhao、Cheng-Zhi Gu、Jing-Gong Liu、Shuang Yang、Xinqiang Fang

  DOI：10.1021/jacs.3c09155

  日期：2023.12.20

  powerful synthetic strategies for making new substances that have been of significant importance in chemistry, medicine, and material fields. Conventional tactics employ various preformed allylation and propargylation reagents. In this study, a conceptually novel copper-catalyzed and B2pin2-mediated Umpolung reactivity of propargylic carbonates has been achieved for the first time, realizing both allylation

  烯丙基化和炔丙基化是制造新物质的两种强大的合成策略，在化学、医学和材料领域具有重要意义。常规策略采用各种预先形成的烯丙基化和炔丙基化试剂。在这项研究中，首次实现了概念上新颖的铜催化和B 2 pin 2介导的炔丙基碳酸酯的Umpolung反应，无需额外的还原剂即可实现醛和酮的烯丙基化和炔丙基化。高效生成了三种烯丙基化产物和一种炔丙基化产物，且所有烯丙基化产物均以顺式构型为主。配体的选择在调节 Umpolung 模式中起着至关重要的作用。合成应用已在包括天然产物合成在内的无数进一步转化中得到证实，并且已进行系统的机理研究以揭示对 Umpolung 过程的详细见解。
• A new protocol for regio- and stereocontrolled aldol reactions through the conjugate addition of dialkylboranes to .alpha.,.beta.-unsaturated ketones
  作者：Gian Paolo Boldrini、Michele Bortolotti、Fabrizio Mancini、Emilio Tagliavini、Claudio Trombini、Achille Umani-Ronchi

  DOI：10.1021/jo00020a025

  日期：1991.9

  A one-pot, two-step procedure, consisting of the 1,4-addition of dialkylboranes to beta-substituted (E)-alpha,beta-unsaturated ketones followed by the reaction of the resulting configurationally pure (Z)-(vinyloxy)boranes with aldehydes, is reported. The overall process corresponds to a regio- and stereocontrolled aldol addition of an unsymmetrical ketone to an aldehyde. A concerted 1,4-addition mechanism accounts for the stereochemical outcome of the hydroboraton reaction; cyclic enones do not undergo conjugate addition, while (Z)-beta-substituted or beta,beta-disubstituted alpha,beta-unsaturated ketones still react in a 1,4-fashion, but with a slower rate and a lower degree of chemoselectivity with respect to beta-substituted (E)-alpha,beta-unsaturated ketones. In the cases of alpha,beta-disubstituted alpha,beta-unsaturated ketones and (E)-(S-phenylthio)cinnammate, which react with dicyclohexylborane to give a mixture of E and Z enolates, an alternative mechanism is proposed.
• A new approach to (Z)-vinyloxyboranes via 1,4 hydroboration of (E)-α,β-unsaturated ketones. Synthesis of syn aldols
  作者：Gian Paolo Boldrini、Fabrizio Mancini、Emilio Tagliavini、Claudio Trombini、Achille Umani-Ronchi

  DOI：10.1039/c39900001680

  日期：——

  (Z)-Vinyloxy boranes are obtained via 1,4-hydroboration of acyclic disubstituted (E)-α,β-unsaturated ketones with dicyclohexylborane or diisopinocampheylborane in tetrahydrofuran, CH2Cl2 or CHCl3 at 20 °C; treatment of the hydroboration mixture with an aldehyde allows pure syn aldols to be synthesized in good yields, and in excellent enantiomeric excesses, using the latter borane.

  （Z）-乙烯基氧基硼烷是通过在20°C下于四氢呋喃，CH 2 Cl 2或CHCl 3中将无环二取代的（E）-α，β-不饱和酮与二环己基硼烷或二异樟脑环硼烷进行1,4-氢硼化而制得的; 用醛处理加氢硼化混合物可使用后者的硼烷以高收率和极佳的对映体过量合成纯的合成醇醛。