(E)-2-oxo-2-phenylethyl but-2-enoate | 145629-72-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-oxo-2-phenylethyl but-2-enoate
• 英文别名: 2-oxo-2-phenylethyl (E)-but-2-enoate；3-oxo-2-phenylethyl (E)-but-2-enoate；(E)-2-oxo-2-phenylethyl crotonate；phenacyl (E)-but-2-enoate
• CAS: 145629-72-7
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: IIOAYLZAZYIHBG-QHHAFSJGSA-N

物化性质

• 沸点：
  318.6±25.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (E)-2-oxo-2-phenylethyl but-2-enoate 在 乙酰胺 、 三氟化硼乙醚 作用下， 反应 12.0h， 以80%的产率得到(E)-4-phenyl-2-(prop-1-enyl)oxazole
  参考文献：
  名称：

  优化氧化金催化的 P,N-双齿配体：羧酸有效分子间捕获 α-氧代金卡宾

  摘要：

  控制确认：P,N-双齿配体 ( L ) 的优化揭示了构象控制对于反应性 α-氧代金卡宾中间体的分子间捕获的重要性。因此，在温和的反应条件下，可以从易得的羧酸和末端炔烃高效且广泛地合成羧甲基酮。

  DOI：

  10.1002/anie.201301601
• 作为产物：
  描述：

  氯甲基丁-2-烯酸酯 在 sodium iodide 、 锌 作用下， 以 丙酮 为溶剂， 反应 11.08h， 生成 (E)-2-oxo-2-phenylethyl but-2-enoate
  参考文献：
  名称：

  Preparation and reactivity of highly functionalized organometallics at the .alpha. position of oxygen or nitrogen

  摘要：

  Alpha-Halogenoalkyl carboxylates (FG-R1CH(X)(OCOR2); FG = COOR, CN, SR; X = I, Br) were readily prepared by the addition of an acid chloride or bromide (R2COX; X = Br or Cl) to an aldehyde (FG-RCHO) in the presence of a catalytic amount of ZnCl2. They insert efficiently zinc dust in THF-DMSO (X = Br, 8-10-degrees-C, 6-10 h) affording the corresponding zinc organometallics at the a position to oxygen FG-RCH(ZnBr)(OAc). After the addition of the THF-soluble copper salt CuCN.2LiCl, the corresponding copper reagents FG-RCH(Cu(CN)ZnBr)(OAc) are formed and reacted with various classes of electrophiles such as acid chlorides, aldehydes, enones, allylic and alkynyl halides, activated alkynes, nitro olefins and alkylidenemalonates providing polyfunctional molecules in excellent yields. Similarly, zinc organometallics at the a position to the nitrogen of cyclic imides were prepared by the zinc insertion to cyclic alpha-chloromethyl (or alpha-chloroethyl) imides. After their transmetalation to the corresponding copper organometallic ((R1CO)2NCH(R)(Cu(CN)ZnCl); R = Me or H), they were reacted with allylic and alkynyl halides and ethyl propiolate affording polyfunctional imides. The reaction of cyclic N-(chloromethyl)imides with aldehydes in the presence of chromium(II) chloride in THF furnishes protected amino alcohols in 36-95% yield.

  DOI：

  10.1021/jo00055a010

文献信息

• Crotonsäure-phenacylester und ihre Verwendung als Linker
  申请人：ORPEGEN Pharma GmbH

  公开号：EP0575779A1

  公开（公告）日：1993-12-29

  Die Erfindung betrifft neue Crotonsäure-phenacylesterverbindungen und ihre Verwendung zum Aufbau von Festphasensystemen für Festphasenreaktionen, insbesondere zur Festphasensynthese von Peptiden, Glykopeptiden oder Proteinen.

  本发明涉及新的巴豆酸苯甲酰酯化合物及其在构建固相反应固相体系中的用途，特别是用于肽、糖肽或蛋白质的固相合成。
• I₂-Catalyzed Regioselective Oxo- and Hydroxy-acyloxylation of Alkenes and Enol Ethers: A Facile Access to α-Acyloxyketones, Esters, and Diol Derivatives
  作者：Rambabu N. Reddi、Pragati K. Prasad、Arumugam Sudalai

  DOI：10.1021/ol5027393

  日期：2014.11.7

  I-2-catalyzed oxo-acyloxylation of alkenes and enol ethers with carboxylic acids providing for the high yield synthesis of a-acyloxyketones and esters is described. This unprecedented regioselective oxidative process employs TBHP and Et3N in stoichiometric amounts under metal-free conditions in DMSO as solvent. Additionally, I-2-catalysis allows the direct hydroxy-acyloxylation of alkenes with the sequential addition of BH3 center dot SMe2 leading to monoprotected diol derivatives in excellent yields.
• Cu(I)-Catalyzed Reductive Aldol Cyclizations:  Diastereo- and Enantioselective Synthesis of β-Hydroxylactones
  作者：Hon Wai Lam、Pekka M. Joensuu

  DOI：10.1021/ol051649h

  日期：2005.9.1

  Copper bisphosphine complexes catalyze the intramolecular reductive aldol reaction of alpha,beta-unsaturated esters with ketones, affording five-and six-membered beta-hydroxylactones in high stereoselectivities. Utilization of chiral nonracemic bisphosphines render the cyclizations enantioselective.
• Knochel Paul, Chou Tso-Sheng, Jubert Carole, Rajagopal Duddu, J. Org. Chem., 58 (1993) N 3, S 588-599
  作者：Knochel Paul, Chou Tso-Sheng, Jubert Carole, Rajagopal Duddu

  DOI：——

  日期：——
• US7732416B2
  申请人：——

  公开号：US7732416B2

  公开（公告）日：2010-06-08