2-溴乙基-2-氧代-2-苯基乙酸酯 | 25315-30-4

• 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: 2-溴乙基-2-氧代-2-苯基乙酸酯
• 英文名称: 2-bromoethyl 2-oxo-2-phenylacetate
• CAS: 25315-30-4
• 化学式: C₁₀H₉BrO₃
• 分子量: 257.084
• InChiKey: MUWSPXUCLRDFRU-UHFFFAOYSA-N

物化性质

• 沸点：
  321.8±25.0 °C(Predicted)
• 密度：
  1.506±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-2-丁烯 、 2-溴乙基-2-氧代-2-苯基乙酸酯 在 [Ir(dF(CF₃)ppy)₂(dtbbpy)]BAr^F 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以69%的产率得到2-bromoethyl 3,3,4,4-tetramethyl-2-phenyloxetane-2-carboxylate
  参考文献：
  名称：

  α-酮酯在三重敏化和光氧化还原条件下的发散光催化反应。

  摘要：

  过渡金属光催化剂的长寿命三重激发态可以通过能量或电子转移途径激活有机底物，这些过程的速率可以通过反应条件的合理调整来影响。然而，生成的特征反应中间体是不同的，并且可以表现出非常不同的反应模式。因此，可用于光催化反应的这种机械多样性可能为设计发散反应提供了机会，这些反应在表面相似的条件下产生明显不同的化学结果。在这里，我们表明苯甲酰甲酸酯与烯烃的光催化反应可以分别在有利于能量转移或电子转移的条件下进行 Paternò-Büchi 环加成或烯丙基官能化反应。

  DOI：

  10.1021/acs.orglett.0c02314
• 作为产物：
  描述：

  苯甲酰甲酸 、 2-溴乙醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以92%的产率得到2-溴乙基-2-氧代-2-苯基乙酸酯
  参考文献：
  名称：

  MICROCAPSULES CONTAINING A GAS-GENERATING PHOTOLABILE POLYMER AND USES THEREOF

  摘要：

  本发明涉及水分散微胶囊，其中包含油相，例如香水，其中包含具有α-酮酸或α-酮酯基团的光敏聚合物，能够在光照下产生气体。气体能够引起微胶囊的扩展或破裂，从而释放油相，从而增加气味感知的持久性。本发明还涉及在香水中使用上述微胶囊，以及包含本发明的微胶囊的香料组合物或香料制品，以提供香气分子的持续释放。

  公开号：

  US20170266103A1

文献信息

• Cu-Catalyzed Esterification Reaction via Aerobic Oxygenation and C–C Bond Cleavage: An Approach to α-Ketoesters
  作者：Chun Zhang、Peng Feng、Ning Jiao

  DOI：10.1021/ja4085463

  日期：2013.10.9

  The Cu-catalyzed novel aerobic oxidative esterification reaction of 1,3-diones for the synthesis of α-ketoesters has been developed. This method combines C-C σ-bond cleavage, dioxygen activation and oxidative C-H bond functionalization, as well as provides a practical, neutral, and mild synthetic approach to α-ketoesters which are important units in many biologically active compounds and useful precursors

  已开发出用于合成 α-酮酯的 Cu 催化的新型 1,3-二酮有氧氧化酯化反应。该方法结合了 CC σ-键裂解、双氧活化和氧化 CH 键功能化，并为 α-酮酯提供了一种实用、中性和温和的合成方法，α-酮酯是许多生物活性化合物中的重要单元和各种有用的前体。功能组转换。在机理研究的基础上提出了一个合理的激进过程。
• I2/TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C–C Bond Cleavage
  作者：Xiang Fang、Xueyan Yang、Tongle Shao、Jun Zhou、Chen Jin、Fanhong Wu

  DOI：10.1055/s-0036-1588833

  日期：2017.9

  A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I2/TBHP promoted sequential iodination, C–C bond cleavage, C–O bond formation and oxidation pathway is involved in this reaction.

  已经开发出一种三氟甲基 β-二酮与醇的无金属氧化偶联反应，用于以良好到优异的产率合成 α-酮酯。初步机理研究表明，I2/TBHP 促进了顺序碘化、C-C 键断裂、C-O 键形成和氧化途径参与该反应。
• Microcapsules containing a gas-generating photolabile polymer and uses thereof
  申请人：Firmenich SA

  公开号：US10105311B2

  公开（公告）日：2018-10-23

  The present invention relates to water-dispersable microcapsules comprising an oil phase, e.g. a perfume, containing a photolabile polymer comprising α-ketoacid or α-ketoester group capable of generating a gas upon exposure to light. The gas is able to cause an extension or the breaking of the microcapsule allowing the release of the oil phase and thus increasing the long-lastingness of the odor perception. The present invention concerns also the use of said microcapsules in perfumery as well as perfuming compositions or perfumed articles comprising the invention's microcapsules to provide a prolonged release of fragrant molecules.

  本发明涉及可在水中分散的微胶囊，该微胶囊由油相（如香水）组成，含有光敏聚合物，该聚合物由α-酮酸或α-酮酯基团组成，在光照下能够产生气体。气体能使微胶囊扩展或破裂，使油相释放出来，从而增加气味感知的持久性。本发明还涉及上述微胶囊在香水以及包含本发明微胶囊的香水组合物或香水制品中的使用，以提供香味分子的持久释放。
• Photochemical Reactions of Halo-/Aryl Sulfide-Substituted Alkyl Phenylglyoxylate, an Assessment of the Lifetime of the Intermediate 1,4-Biradical
  作者：Shengkui Hu、Douglas C. Neckers

  DOI：10.1021/jo971201x

  日期：1997.10.1

  Photochemical reactions of several halo/aryl sulfide-substituted alkyl phenylglyoxylates (1) were studied. For 2'-bromo-(Ib), 2'-iodo- (1c), 2'-(phenylthio)- (1d), and 2'-(phenylsulfinyl)- (1e) ethyl phenylglyoxylate, vinyl phenylglyoxylate (2), proposed to be the result of beta-elimination from the 1,4-biradical formed by triplet state gamma-hydrogen abstraction, is the dominant photoproduct. In the cases Ib and Id Norrish Type II products were also observed. Vinyl phenylglyoxylate (2) was not observed with 2'-chloroethyl (la), 3'-bromopropyl (If), and 3'-(phenylthio)propyl (1g) phenylglyoxylate. The lifetime of the 1,4-biradical intermediate is deduced from the competition between the beta-elimination of the monoradical and the normal biradical decay. The triplet lifetime and the photoreaction efficiency of 1 were not significantly affected by halogen-substitution.
• [EN] MICROCAPSULES CONTAINING A GAS-GENERATING PHOTOLABILE POLYMER AND USES THEREOF<br/>[FR] MICROCAPSULES CONTENANT UN POLYMÈRE PHOTOLABILE À LIBÉRATION DE GAZ ET LEURS UTILISATIONS
  申请人：FIRMENICH & CIE

  公开号：WO2016083321A1

  公开（公告）日：2016-06-02

  The present invention relates to water-dispersable microcapsules comprising an oil phase, e.g. a perfume, containing a photolabile polymer comprising α-ketoacid or α- ketoester group capable of generating a gas upon exposure to light. The gas is able to cause an extension or the breaking of the microcapsule allowing the release of the oil phase and thus increasing the long-lastingness of the odor perception. The present invention concerns also the use of said microcapsules in perfumery as well as perfuming compositions or perfumed articles comprising the invention's microcapsules to provide a prolonged release of fragrant molecules.