methyl (2Z)-3-(furan-2-yl)-2-methylprop-2-enoate | 85673-23-0

• 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: methyl (2Z)-3-(furan-2-yl)-2-methylprop-2-enoate
• 英文别名: methyl (Z)-3-(2-furfuryl)-2-methyl-2-propenoate；(Z)-methyl 3-(2-furyl)-2-methylprop-2-enoate；methyl 3-(2-furyl)-2-methylprop-2-enoate；methyl (Z)-2-methyl-3-(2-furyl)propenoate；methyl (Z)-3-(furan-2-yl)-2-methylprop-2-enoate
• CAS: 85673-23-0
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: WUWDAOLJZHBHPV-SREVYHEPSA-N

物化性质

• 沸点：
  228.8±15.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-(acetoxy(furan-2-yl)methyl)acrylate 在 palladium diacetate 、 甲酸 、 三乙胺 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以65%的产率得到methyl (2Z)-3-(furan-2-yl)-2-methylprop-2-enoate
  参考文献：
  名称：

  Palladium catalysed regio and stereoselective reduction of Baylis-Hillman coupling products derived allylic acetates

  摘要：

  Acetates derived front a variety of the Baylis-Hillman products undergo reduction with HCOOH in the presence of Et3N. Pd(OAc)(2), and dppe (or tri-isopropylphosphite) to yield the corresponding trisubstituted Z-olefins in good yields displaying high regio and stereoselectivity. (C) 1998 Published by Elsevier Science Ltd. All lights reserved.

  DOI：

  10.1016/s0040-4039(98)01049-1

文献信息

• Part I: The Development of the Catalytic Wittig Reaction
  作者：Christopher J. O'Brien、Zachary S. Nixon、Andrew J. Holohan、Stephen R. Kunkel、Jennifer L. Tellez、Bryan J. Doonan、Emma E. Coyle、Florie Lavigne、Lauren J. Kang、Katherine C. Przeworski

  DOI：10.1002/chem.201301444

  日期：2013.11.4

  developed the first catalytic (in phosphane) Wittig reaction (CWR). The utilization of an organosilane was pivotal for success as it allowed for the chemoselective reduction of a phosphane oxide. Protocol optimization evaluated the phosphane oxide precatalyst structure, loading, organosilane, temperature, solvent, and base. These studies demonstrated that to maintain viable catalytic performance it was

  我们开发了第一个催化（在膦中）维蒂希反应（CWR）。有机硅烷的使用对于成功至关重要，因为它可以使氧化膦的化学选择性还原。方案优化评估了氧化膦预催化剂的结构，负载量，有机硅烷，温度，溶剂和碱。这些研究表明，要保持可行的催化性能，必须使用1型环状氧化膦预催化剂。最初的底物研究以碳酸钠为碱，进一步的实验确定了N，N-二异丙基乙胺（DIPEA）作为可溶性替代品。DIPEA的使用提高了易用性，拓宽了底物范围，并降低了催化剂前负荷。优化的方案与烷基，芳基和杂环（呋喃基，吲哚基，吡啶基，吡咯基和噻吩基）醛兼容，可通过使用预催化剂以中等至高产率（60-96％）生产二取代和三取代的烯烃。负载量为4-10 mol％。动力学E / Z选择性通常为66:34；通过膦介导的异构化事件实现了对二取代的α，β-不饱和产物的完全E选择性。CWR用于合成54，这是抗阿尔茨海默病药物盐酸多奈哌齐的已知前体，以克为单位（12.2
• Breaking the Ring through a Room Temperature Catalytic Wittig Reaction
  作者：Christopher J. O'Brien、Florie Lavigne、Emma E. Coyle、Andrew J. Holohan、Bryan J. Doonan

  DOI：10.1002/chem.201300546

  日期：2013.5.3

  One ring no longer rules them all: Employment of 2.5–10 mol % of 4‐nitrobenzoic acid with phenylsilane led to the development of a room temperature catalytic Wittig reaction (see scheme). Moreover, these enhanced reduction conditions also facilitated the use of acyclic phosphine oxides as catalysts for the first time. A series of alkenes were produced in moderate to high yield and selectivity.

  一个环不再完全统治一切：用2.5-10 mol％的4-硝基苯甲酸与苯基硅烷一起使用导致了室温催化Wittig反应的发展（参见方案）。此外，这些增强的还原条件还促进了首次将无环氧化膦用作催化剂。以中等至高收率和选择性生产了一系列烯烃。
• Reductive dehydroxylation of Baylis–Hillman adducts with low-valent titanium reagent: syntheses of stereoselective trisubstituted alkenes
  作者：Uma Shadakshari、Sandip K Nayak

  DOI：10.1016/s0040-4020(01)00333-7

  日期：2001.5

  The Baylis–Hillman adducts prepared from aromatic aldehydes and methyl acrylate underwent smooth dehydroxylation with concomitant olefin isomerisation with low-valent titanium reagent to provide the trisubstituted alkenes with high (E)-selectivity.

  由芳族醛和丙烯酸甲酯制得的Baylis-Hillman加合物经过顺畅的脱羟基反应，并伴随有低价钛试剂的烯烃异构化反应，从而为三取代烯烃提供了高（E）选择性。
• Dandarova, Miloslava; Kovac, Jaroslav; Vegh, Daniel, Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 12, p. 3412 - 3417
  作者：Dandarova, Miloslava、Kovac, Jaroslav、Vegh, Daniel、Zvak, Vladimir

  DOI：——

  日期：——
• Palladium catalysed regio and stereoselective reduction of Baylis-Hillman coupling products derived allylic acetates
  作者：Kandaswamy Pachamuthu、Yashwant D. Vankar

  DOI：10.1016/s0040-4039(98)01049-1

  日期：1998.7

  Acetates derived front a variety of the Baylis-Hillman products undergo reduction with HCOOH in the presence of Et3N. Pd(OAc)(2), and dppe (or tri-isopropylphosphite) to yield the corresponding trisubstituted Z-olefins in good yields displaying high regio and stereoselectivity. (C) 1998 Published by Elsevier Science Ltd. All lights reserved.