3-Acetoxy-2-methylene-undecanoic acid methyl ester | 594835-16-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-Acetoxy-2-methylene-undecanoic acid methyl ester
• 英文别名: Undecanoic acid, 3-(acetyloxy)-2-methylene-, methyl ester；methyl 3-acetyloxy-2-methylideneundecanoate
• CAS: 594835-16-2
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: OQKRYSSAJQLEBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sodium 4-methylbenzenesulfinate 、 3-Acetoxy-2-methylene-undecanoic acid methyl ester 在 1-n-butyl-methylimidazolium tetrafluoroborate 作用下， 反应 3.0h， 以90%的产率得到(E)-2-(Toluene-4-sulfonylmethyl)-undec-2-enoic acid methyl ester
  参考文献：
  名称：

  Preparation of substituted allyl acetates and sulfones from Baylis–Hillman adducts in ionic liquid media

  摘要：

  Reactions of potassium acetate and the sodium salt of p-toluenesulfinic acid with acetates of Baylis-Hillman adducts produce substituted allyl acetates and allyl sulfones respectively. Ionic liquids are utilized in place of conventional solvents. (C) 2003 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(03)01073-6

文献信息

• Basavaiah, Deevi; Reddy, Ravi Mallikarjuna, Journal of Chemical Research, Miniprint, 2001, # 9, p. 947 - 956
  作者：Basavaiah, Deevi、Reddy, Ravi Mallikarjuna

  DOI：——

  日期：——
• Palladium-Catalyzed Cross-Coupling of Baylis−Hillman Acetate Adducts with Organosilanes
  作者：George W. Kabalka、Gang Dong、Bollu Venkataiah、Chunlan Chen

  DOI：10.1021/jo051177k

  日期：2005.11.1

  A cross-coupling reaction between acetates of Baylis-Hillman adducts and organosilanes is described. A nonconventional solvent poly(ethylene glycol) (PEG) is used as the reaction medium.
• Baylis–Hillman chemistry: a one pot cross-coupling/allylboration reaction
  作者：George W. Kabalka、Bollu Venkataiah、Gang Dong

  DOI：10.1016/j.tetlet.2005.04.055

  日期：2005.6

  A one pot sequential cross-coupling/allylboration is described. Baylis-Hillman acetate adducts couple with bis(pinacolato)diboron to form substituted allylboronates, which react with aldehydes in the presence of a silica supported BF3 catalyst to form highly functionalized homoallylic alcohols in excellent yields. (c) 2005 Elsevier Ltd. All rights reserved.
• Pd-Catalyzed Cross-Coupling of Baylis−Hillman Acetate Adducts with Bis(pinacolato)diboron:  An Efficient Route to Functionalized Allyl Borates
  作者：George W. Kabalka、Bollu Venkataiah、Gang Dong

  DOI：10.1021/jo0492618

  日期：2004.8.1

  The cross-coupling of Baylis-Hillman acetate adducts and bis(pinacolato)diboron proceeds readily in high yields in the presence of palladium catalyst to produce 3-substituted-2-alkoxycarbonyl allylboronates. These allylboronates can be transformed to stable allyl trifluoroborate salts by addition of excess aqueous KHF2. Both the allylboronate and allyltrifluoroborate derivatives react with aldehydes to afford functionalized homoallylic alcohols stereo-selectively.
• Palladium-Catalyzed Regio- and Stereoselective Cross-Coupling of Baylis-Hillman Adducts and Bimetals:  A Novel Method for the Synthesis of Substituted Allylsilanes and Allylgermanes
  作者：George W. Kabalka、Bollu Venkataiah、Gang Dong

  DOI：10.1021/om0492451

  日期：2005.2.1

  Cross-coupling reactions between Baylis-Hillman acetate adducts and bimetallic reagents (Si-Si, Ge-Ge) catalyzed by a phosphine-free palladium complex are described. 3-Substituted-2-carbonylallylsilanes and allylgermanes were isolated in high yields. The cross-coupling reactions are regio- and stereoselective.