1,2-Bis(4-chlorophenyl)-2-hydroxy-4-penten-1-one | 130649-65-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-Bis(4-chlorophenyl)-2-hydroxy-4-penten-1-one
• 英文别名: 2-hydroxy-1,2-bis(4-chlorophenyl)-4-penten-1-one；1,2-bis(4-chlorophenyl)-2-hydroxypent-4-en-1-one
• CAS: 130649-65-9
• 化学式: C₁₇H₁₄Cl₂O₂
• 分子量: 321.203
• InChiKey: YFLCAIXYSRRWPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3-溴丙烯 、 1,2-双(4-氯苯基)-2-羟基乙酮 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 以56 %的产率得到1,2-Bis(4-chlorophenyl)-2-hydroxy-4-penten-1-one
  参考文献：
  名称：

  tBuOK/TMSOK 介导的“烷基卤化物到烷基自由基”转变，用于过渡-无金属的苯甲醛 α-C—H 烷基化

  摘要：

  碱叔丁醇（tBuOK 或 tBuONa）介导的芳基碘化物生成芳基自由基是自由基化学中的一项里程碑式发现。然而，等效的“烷基卤化物到烷基自由基”的转化尚未通过类似的催化策略在适用的合成中实现。在本文中，提出了安息香酯直接 α-C-H 烷基化中由 tBuOK 或 TMSOK 介导的首个实用的“烷基卤化物到烷基自由基”转变。作为芳基自由基生成等同等重要的问题，目前的工作虽然为合成多种安息香蛋白带来了一种相当简单和有用的新方法，但通过展示简单碱基介导的自由基形成的更高通用性，也代表了基于烷基自由基的合成中的重要一步。

  DOI：

  10.1002/cjoc.202400664

文献信息

• Photochemically Induced Single Electron Transfer Reactions of Benzils with Allylstannane. Direct Observation of Reactive Intermediates by ESR Method
  作者：Kazuhiro Maruyama、Yoshihiro Matano

  DOI：10.1246/bcsj.63.2218

  日期：1990.8

  Although the photochemically induced reaction of benzil with allyltrimethylstannane in benzene afforded α-allylbenzoin as a major product, benzil did not react thermally with the same reagent. An ESR observation disclosed that the benzil anion radical ion-paired upon contact with trimethylstannyl cation (BSnMe3) was generated during irradiation. Its structure was confirmed by the detection of satellite

  尽管苄基与烯丙基三甲基锡烷在苯中的光化学诱导反应提供了 α-烯丙基安息香作为主要产物，但苄基不与相同的试剂发生热反应。ESR 观察表明，与三甲基甲锡基阳离子 (BSnMe3) 接触后会发生离子配对的苄基阴离子自由基是在辐射过程中产生的。它的结构通过检测锡同位素产生的卫星信号得到证实。此外，在含有苄基和烯丙基锡烷的固溶体在 77 K 光解过程中也观察到了三线态自由基对。该反应通过从烯丙基锡烷到光激发的苄基的单电子转移进行，然后断裂的 C-Sn 键烯丙基锡阳离子自由基。最终，
• Photoinduced Platinum-Catalyzed Reductive Allylation of α-Diketones with Allylic Carbonates
  作者：Junpei Shimosato、Masaya Sawamura、Yusuke Masuda

  DOI：10.1021/acs.orglett.4c00091

  日期：2024.3.15

  A unique process for the photoinduced platinum-catalyzed reductive allylation of α-diketones with allylic carbonates has been developed. This allylation reaction was found to proceed selectively at the more electron-deficient carbonyl group of the diketone to afford an α-keto homoallylic alcohol. Such products could be further derivatized by transformation of the remaining carbonyl group. A mechanistic

  已经开发出一种独特的光诱导铂催化 α-二酮与烯丙碳酸酯还原烯丙基化的方法。发现这种烯丙基化反应选择性地在二酮的缺电子羰基上进行，得到α-酮高烯丙醇。此类产物可以通过剩余羰基的转化进一步衍生。机理研究表明，光照射产生的羰基自由基与（π-烯丙基）铂络合物反应形成 C-C 键。
• Palladium-Catalyzed C-Allylation of Benzoins and an NHC-Catalyzed Three Component Coupling Derived Thereof: Compatibility of NHC- and Pd-Catalysts
  作者：Raphaël Lebeuf、Keiichi Hirano、Frank Glorius

  DOI：10.1021/ol801644f

  日期：2008.10.2

  A large range of benzoins was successfully applied as C-nucleophiles in the palladium-catalyzed allylic alkylation with several allyl acetates, resulting in functionalized tertiary homoallylic alcohols. A number of unsymmetrical benzoins can be coupled with high levels of regio- and chemoselectivity. Finally, the challenging compatibility of free N-heterocyclic carbenes with a palladium catalyst has been utilized in a number of metal- and organocatalyzed three-component coupling reactions.
• Assembly of functionalized α-hydroxy carbonyl compounds via combination of N-heterocyclic carbene and Pd catalysts
  作者：Jinmei He、Shibing Tang、Shouchu Tang、Jian Liu、Yongquan Sun、Xinfu Pan、Xuegong She

  DOI：10.1016/j.tetlet.2008.11.032

  日期：2009.1

  Functionalized a-hydroxy carbonyl compounds were prepared from various aldehydes and allylic acetates via a multicomponent reaction, which were catalyzed by N-heterocyclic carbene and Pd catalysts in one pot. (c) 2008 Elsevier Ltd. All rights reserved.
• Takuwa, Akio; Nishigaichi, Yutaka; Yamashita, Koichi, Chemistry Letters, 1990, # 4, p. 639 - 642
  作者：Takuwa, Akio、Nishigaichi, Yutaka、Yamashita, Koichi、Iwamoto, Hidetoshi

  DOI：——

  日期：——