2-methyl-3-isopropyl-3-heptyl 3-oxobutanoate | 125640-99-5

• 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-methyl-3-isopropyl-3-heptyl 3-oxobutanoate
• 英文别名: (2-methyl-3-propan-2-ylheptan-3-yl) 3-oxobutanoate
• CAS: 125640-99-5
• 化学式: C₁₅H₂₈O₃
• 分子量: 256.386
• InChiKey: LILSIIGXGWACEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  273.5±8.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-methyl-3-isopropyl-3-heptyl 3-oxobutanoate 在 氢氧化钾 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 生成 2-methyl-3-isopropyl-3-heptyl diazoacetate
  参考文献：
  名称：

  Doyle, Michael P.; Bagheri, Vahid; Wandless, Thomas J., Journal of the American Chemical Society, 1990, vol. 112, # 5, p. 1906 - 1912

  摘要：

  DOI：
• 作为产物：
  描述：

  双乙烯酮 、 2-methyl-3-isopropylheptane-3-ol 在 sodium acetate 作用下， 反应 1.5h， 以59%的产率得到2-methyl-3-isopropyl-3-heptyl 3-oxobutanoate
  参考文献：
  名称：

  Doyle, Michael P.; Bagheri, Vahid; Wandless, Thomas J., Journal of the American Chemical Society, 1990, vol. 112, # 5, p. 1906 - 1912

  摘要：

  DOI：

文献信息

• Electronic and steric control in carbon-hydrogen insertion reactions of diazoacetoacetates catalyzed by dirhodium(II) carboxylates and carboxamides
  作者：Michael P. Doyle、Larry J. Westrum、Wendelmoed N. E. Wolthuis、Marjorie M. See、William P. Boone、Vahid Bagheri、Matthew M. Pearson

  DOI：10.1021/ja00056a021

  日期：1993.2

  Carboxylate and carboxamide ligands on dirhodium(II) catalysts can provide enormous regiocontrol in carbon-hydrogen insertion reactions of diazoacetate esters. Whereas 2,3,4-trimethyl-3-pentyl diazoacetoacetate (1) forms gamma-lactone products from insertion into primary and tertiary C-H bonds in a statistical distribution (61:39) with dirhodium(II) tetrakis(perfluorobutyrate), only tertiary C-H insertion is observed with dirhodium(II) tetraacetamide. Similar results are obtained with 2-methyl-2-octyl diazoacetoacetate (3), where competition for insertion exists between secondary and primary C-H bonds and electronic factors govern regioselection. However, with 2-methyl-3-isopropyl-3-heptyl diazoacetoacetate (2) and 2-methyl-1-phenyl-2-propyl diazoacetoacetate (4), product distributions from C-H insertion are invariant with the dirhodium(II) ligands; insertion into a secondary C-H bond is favored over tertiary C-H insertion with 2 (95:5), and insertion into a primary C-H bond is preferred to benzylic secondary C-H insertion with 4 (70:30). In such cases, which are amenable to analyses by MM2 calculations, regioselectivity is determined by conformational preferences for which C-H insertion selectivity can be as random as that found with 2 and 4. When only one C-H bond site is available for insertion to form a five-membered ring product, only one gamma-lactone is observed from reactions catalyzed by dirhodium(II) tetraacetate, and that product is not necessarily the one predicted by presumed electronic preferences.