(E)-methyl 2-acetylhex-4-enoate | 103185-14-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (E)-methyl 2-acetylhex-4-enoate
• 英文别名: methyl (E)-2-acetylhex-4-enoate
• CAS: 103185-14-4
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: HRIIIARODJZKNK-SNAWJCMRSA-N

物化性质

• 沸点：
  214.3±20.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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)-methyl 2-acetylhex-4-enoate 在 polymer-supported selenium bromide resin 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 2-methyl-5-vinyl-4,5-dihydrofuran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Polymer-supported selenium-induced electrophilic cyclization: solid-phase synthesis of poly-substituted dihydrofurans and tetrahydrofurans

  摘要：

  Poly-substituted dihydrofurans and tetrahydrofurans have been synthesized through polymer-supported selenium-induced intramolecular electrophilic cyclization, followed by selenoxide syn-elimination or novel nucleophilic substitution cleavage of selenium resin with good yields and purities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.042
• 作为产物：
  描述：

  (E)-2-丁烯基乙酸酯 、 Na-Salz des Acetessigsaeure-methylester 在 四(三苯基膦)钯 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以54%的产率得到(E)-methyl 2-acetylhex-4-enoate
  参考文献：
  名称：

  Fluorinated allylic alcohols as building blocks

  摘要：

  A theoretical study on the carbocationic reactivity of 2-fluoroallylic alcohols and derivatives explains some experimental findings. An outline is also given of synthetic approaches towards fluoroallylic amines and more complex carbon skeletons starting with fluoroallylic alcohols.

  DOI：

  10.1016/0022-1139(94)00415-c

文献信息

• Copper(I) promoted CC bond forming reactions: direct activation of allyl alcohols
  作者：Jubaraj.B. Baruah、Ashoka G. Samuelson

  DOI：10.1016/0022-328x(89)87015-9

  日期：1989.2

  Allylic alcohols, acetates, carbonates and chlorides can be activated by copper(I) salts towards nucleophilic substitution by carbon nucleophiles under relatively mild conditions.

  烯丙醇，乙酸盐，碳酸盐和氯化物可以在相对温和的条件下被铜（I）盐活化，以被碳亲核试剂亲核取代。
• Palladium-catalyzed desulfinylative C–C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters
  作者：Chandra M. Rao Volla、Srinivas Reddy Dubbaka、Pierre Vogel

  DOI：10.1016/j.tet.2008.11.007

  日期：2009.1

  (E)-but-2-enesulfonyl chlorides have been used as electrophilic partners in desulfinylative palladium-catalyzed C–C coupling with Grignard reagents and sodium salts of dimethyl malonate and methyl acetoacetate. Neopentyl alk-2-ene sulfonates can also be used as electrophilic partners in desulfinylative allylic arylations and allylic alkylations. The regioselectivity of the allylic arylation and alkylation depends

  2-甲基丙-2-烯-，丙-2-烯-，1-甲基丙-2-烯-和（E）-丁-2-烯磺酰氯已被用作脱亚磺酰基钯催化的CC的亲电子伙伴与格氏试剂和丙二酸二甲酯和乙酰乙酸甲酯的钠盐偶合。新戊基烷基-2-烯磺酸盐也可以用作脱亚磺酰基烯丙基芳基化和烯丙基烷基化中的亲电子伙伴。烯丙基芳基化和烷基化的区域选择性取决于催化剂的性质。与PdCl 2（PhCN）2一起，使用1-甲基丙-2-烯-或（E）-丁-2-烯磺酰氯以高区域选择性形成（E）-巴豆基衍生物。
• An Intramolecular Prins Double Cyclization Catalyzed by Silyl Triflates¹
  作者：Michael E. Jung、Steve Angelica、Derin C. D'Amico

  DOI：10.1021/jo971337v

  日期：1997.12.1

  Several intramolecular Prins double cyclizations are reported. The 2-alkyl 5-hepten-1,2-diols and their analogues, 9-11, were prepared and oxidized to the aldehydes 6-8 under Swern conditions. Treatment of these alpha-hydroxy aldehydes with TBSOTf and a hindered base gave the products of an intramolecular Prins double cyclization, namely the 7-(silyloxy)-2-oxabicyclo[2.2.1]heptanes, 17-19, in 84-92% yield. These compounds were formed as single diastereomers with only the anti silyl ethers being obtained. The cyclizations occur when five-membered rings are being formed and when the initially formed cation is highly stabilized. Other substrates do not cyclize, e.g., when the alpha-hydroxy aldehydes 20-22, prepared from 26-28, are treated under similar conditions, none of the corresponding cyclization products, 23-25, were obtained.
• Effective activation of allylic etherrs by boron oxide in palladium catalyzed allylic alkylation
  作者：Xiyan Lu、Xiaohui Jiang

  DOI：10.1016/0022-328x(89)85259-3

  日期：1989.1
• KUROSAWA HIDEO, J. CHEM. SOC. DALTON TRANS., 1979, NO 6, 939-943
  作者：KUROSAWA HIDEO

  DOI：——

  日期：——