O-Octylbutyrolactim

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: O-Octylbutyrolactim
• 英文别名: 5-octoxy-3,4-dihydro-2H-pyrrole
• 化学式: C₁₂H₂₃NO
• 分子量: 197.321
• InChiKey: IRZCXKWEMFGJIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙氧基-4,5-二氢-3H-吡咯 、 辛醇 以 苯 为溶剂， 反应 20.0h， 以84.8%的产率得到O-Octylbutyrolactim
  参考文献：
  名称：

  The Effect of Ring Size on Tetrahedral Displacement Reactions of Cyclic Imidates. Synthesis of O-(Fluoroalkyl)lactim and Higher O-Alkyllactims from Lower O-Alkyllactims

  摘要：

  A recently developed synthesis of 2-(perfluoroalkyl)ethanols (R(F)CH(2)CH(2)OH) is based on heating 2-(perfluoroalkyl)-1-iodoethanes R(F)CH(2)CH(2)I with an amide, e.g., N-methylformamide or a lactam, 2-pyrrolidinone. The presumed O-[2-(perfluoroalkyl)ethyl]lactim intermediates have now been prepared in good to excellent yields (60-90%) by heating a lower molecular mass O-alkyllactim with a higher-boiling alcohol, e.g., with R(F)CH(2)CH(2)OH, to displace the lower boiling alcohol. Competitive rate experiments showed that a 7-membered O-methyllactim reacted four to five times faster than did the 5-membered O-methyllactim. This difference is attributed to increased eclipsing strain, commonly called ''I-strain''. In a ''planar'' 5-membered lactim ring, the engendered eclipsing strain appears to be greater than in the more flexible 7-membered ring. Reactant ratio and reaction conditions also affected the yield of lactim ether. Preparatively, reaction of C6F13CH2CH2OH (3) with O-ethylbutyrolactim (6) gave O-[2-(perfluorohexyl)ethyl]butyrolactim (7) in an 89.2% yield (on unrecovered 3) at 67.9% conversion. Yield was limited by dealkylation and condensation reactions that occurred during long heating times. By contrast, alcohol 3 with O-methylcaprolactim (10) gave 7-membered O-[2-(F-hexyl)ethyl]caprolactim (11) in 98% yield at 90% conversion.

  DOI：

  10.1021/jo00092a028

文献信息

• Brace Neal O., Davidson Barbara C., Shellhamer Dale F., Daniels Mirna, J. Org. Chem, 59 (1994) N 13, S 3670-3675
  作者：Brace Neal O., Davidson Barbara C., Shellhamer Dale F., Daniels Mirna

  DOI：——

  日期：——
• The Effect of Ring Size on Tetrahedral Displacement Reactions of Cyclic Imidates. Synthesis of O-(Fluoroalkyl)lactim and Higher O-Alkyllactims from Lower O-Alkyllactims
  作者：Neal O. Brace、Barbara C. Davidson、Dale F. Shellhamer、Mirna Daniels

  DOI：10.1021/jo00092a028

  日期：1994.7

  A recently developed synthesis of 2-(perfluoroalkyl)ethanols (R(F)CH(2)CH(2)OH) is based on heating 2-(perfluoroalkyl)-1-iodoethanes R(F)CH(2)CH(2)I with an amide, e.g., N-methylformamide or a lactam, 2-pyrrolidinone. The presumed O-[2-(perfluoroalkyl)ethyl]lactim intermediates have now been prepared in good to excellent yields (60-90%) by heating a lower molecular mass O-alkyllactim with a higher-boiling alcohol, e.g., with R(F)CH(2)CH(2)OH, to displace the lower boiling alcohol. Competitive rate experiments showed that a 7-membered O-methyllactim reacted four to five times faster than did the 5-membered O-methyllactim. This difference is attributed to increased eclipsing strain, commonly called ''I-strain''. In a ''planar'' 5-membered lactim ring, the engendered eclipsing strain appears to be greater than in the more flexible 7-membered ring. Reactant ratio and reaction conditions also affected the yield of lactim ether. Preparatively, reaction of C6F13CH2CH2OH (3) with O-ethylbutyrolactim (6) gave O-[2-(perfluorohexyl)ethyl]butyrolactim (7) in an 89.2% yield (on unrecovered 3) at 67.9% conversion. Yield was limited by dealkylation and condensation reactions that occurred during long heating times. By contrast, alcohol 3 with O-methylcaprolactim (10) gave 7-membered O-[2-(F-hexyl)ethyl]caprolactim (11) in 98% yield at 90% conversion.