2-isopropyl-3-methyl-crotonic acid methyl ester | 109899-43-6

• 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: 2-isopropyl-3-methyl-crotonic acid methyl ester
• 英文别名: 2-Isopropyl-3-methyl-crotonsaeure-methylester；Methyl 2-isopropyl-3-methyl-2-butenoate；methyl 3-methyl-2-propan-2-ylbut-2-enoate
• CAS: 109899-43-6
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: RYHBZBYZQYPQSY-UHFFFAOYSA-N

物化性质

• 沸点：
  48 °C(Press: 5 Torr)
• 密度：
  0.9054 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-isopropyl-3-methyl-crotonic acid methyl ester 在 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以72%的产率得到2-isopropyl-3-methyl-crotonic acid
  参考文献：
  名称：

  Axially chiral thioamides of acrylic acid: correlated and uncorrelated internal rotations

  摘要：

  In acrylic thioamides (Scheme 1), two intramolecular motions are possible: thiocarbonyl-nitrogen (=C-N) and alkenyl-carbonyl (=C-C=) rotations. Since the two mobile molecular fragments can interact by steric and by resonance effects, we intended to demonstrate the existence of correlated in addition to the above uncorrelated motions. For each of the three thioamides chosen, at least two of the four stereoisomers were enriched by crystallization and by liquid chromatography on nonracemic sorbents. Thereby axial chirality of acrylic thioamides was proven for the first time. Thermal equilibrations were monitored quantitatively by time-dependent H-1 NMR spectroscopy in the presence of a nonracemic additive, a method which, to our knowledge, has not previously been described. These kinetic results were evaluated by a simulation program with reference to uncorrelated and correlated rotations (Figs. 4-6). We have shown that all of these motions occur in thioamide 14. The enantiomers of thioamide 13 do not interconvert directly. However, indirect, two-step enantiomerizations in 13 have been proven one of the two steps consisting of correlated rotations. The latter are, therefore, possible in acrylic thioamides, a class of compounds which differ considerably from the molecules for which correlated motions were hitherto known. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00373-5
• 作为产物：
  描述：

  methyl 2-isopropyl-3-methylbutanoate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 4.0h， 生成 2-isopropyl-3-methyl-crotonic acid methyl ester
  参考文献：
  名称：

  Furuhata, Akimichi; Hirano, Masachika; Fujimoto, Izumi, Agricultural and Biological Chemistry, 1987, vol. 51, # 6, p. 1633 - 1640

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Visible-Light-Driven Carboxylation of Aryl and Alkenyl Triflates by Using Photoredox Catalysts
  作者：Katsuya Shimomaki、Tomoya Nakajima、Joaquim Caner、Naoyuki Toriumi、Nobuharu Iwasawa

  DOI：10.1021/acs.orglett.9b01340

  日期：2019.6.21

  A visible-light-driven carboxylation of aryl and alkenyl triflates with CO2 is developed by using a combination of Pd and photoredox catalysts. This reaction proceeds under mild conditions and can be applied to a wide range of substrates including acyclic alkenyl triflates.

  通过使用Pd和光氧化还原催化剂的组合，可见光驱动的芳基和烯基三氟甲磺酸酯与CO 2的羧化反应。该反应在温和的条件下进行，可用于多种底物，包括无环烯基三氟甲磺酸酯。
• The Rearrangement of α,α'-Dibromoketones¹
  作者：R. B. Wagner、James A. Moore

  DOI：10.1021/ja01158a085

  日期：1950.2
• FURUHATA, AKIMICHI;HIRANO, MASACHIKA;FUJIMOTO, IZUMI;MATSUI, MASANAO, AGR. AND BIOL. CHEM., 51,(1987) N 6, 1633-1640
  作者：FURUHATA, AKIMICHI、HIRANO, MASACHIKA、FUJIMOTO, IZUMI、MATSUI, MASANAO

  DOI：——

  日期：——
• Furuhata, Akimichi; Hirano, Masachika; Fujimoto, Izumi, Agricultural and Biological Chemistry, 1987, vol. 51, # 6, p. 1633 - 1640
  作者：Furuhata, Akimichi、Hirano, Masachika、Fujimoto, Izumi、Matsui, Masano

  DOI：——

  日期：——
• Axially chiral thioamides of acrylic acid: correlated and uncorrelated internal rotations
  作者：Margit Kuttenberger、Markus Frieser、Martin Hofweber、Albrecht Mannschreck

  DOI：10.1016/s0957-4166(98)00373-5

  日期：1998.10

  In acrylic thioamides (Scheme 1), two intramolecular motions are possible: thiocarbonyl-nitrogen (=C-N) and alkenyl-carbonyl (=C-C=) rotations. Since the two mobile molecular fragments can interact by steric and by resonance effects, we intended to demonstrate the existence of correlated in addition to the above uncorrelated motions. For each of the three thioamides chosen, at least two of the four stereoisomers were enriched by crystallization and by liquid chromatography on nonracemic sorbents. Thereby axial chirality of acrylic thioamides was proven for the first time. Thermal equilibrations were monitored quantitatively by time-dependent H-1 NMR spectroscopy in the presence of a nonracemic additive, a method which, to our knowledge, has not previously been described. These kinetic results were evaluated by a simulation program with reference to uncorrelated and correlated rotations (Figs. 4-6). We have shown that all of these motions occur in thioamide 14. The enantiomers of thioamide 13 do not interconvert directly. However, indirect, two-step enantiomerizations in 13 have been proven one of the two steps consisting of correlated rotations. The latter are, therefore, possible in acrylic thioamides, a class of compounds which differ considerably from the molecules for which correlated motions were hitherto known. (C) 1998 Elsevier Science Ltd. All rights reserved.