5-tert-Butyl-2,2-dimethyl-1-hydroxylpyrrolidine | 62020-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 5-tert-Butyl-2,2-dimethyl-1-hydroxylpyrrolidine
• 英文别名: 2-tert-Butyl-5,5-dimethyl-1-hydroxypyrrolidine；5-tert-Butyl-2,2-dimethylpyrrolidin-1-ol；5-tert-butyl-1-hydroxy-2,2-dimethylpyrrolidine
• CAS: 62020-89-7
• 化学式: C₁₀H₂₁NO
• 分子量: 171.283
• InChiKey: NMODNNVXGIUAGU-UHFFFAOYSA-N

物化性质

• 沸点：
  115-119 °C(Press: 0.01 Torr)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-tert-Butyl-2,2-dimethyl-1-hydroxylpyrrolidine 在 Cu-acetate 、 氨 、 氧气 作用下， 以 乙醇 为溶剂， 以65%的产率得到2-tert-Butyl-5,5-dimethyl-1-pyrroline N-oxide
  参考文献：
  名称：

  Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes

  摘要：

  The 1.3 dipolar cycloaddition of alkynes 4-6 with acyclic nitrones 1-3, 23 and 24 as well as with cyclic nitrones 27 is studied. As was found for the reaction of the aldonitrones 1-3 an increased portion of 5-regioisomers is formed with increasing steric demand of either of the two substituents, the C-alkyl substituent R2 and the N-alkyl substituent R1. Thus the conclusion is drawn that cycloaddition of 1-3 proceeds not only via transition states arising from Z-nitrones but also via transition states developing from E-nitrones, although in the ground-state the Z-isomer is favored to a considerable extent. In this context steric destabilization of the transition states is discussed qualitatively.

  DOI：

  10.1016/s0040-4020(01)88127-8
• 作为产物：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 在 ammonium hydroxide 、 lithium aluminium tetrahydride 、 氧气 、 copper diacetate 作用下， 以 乙醚 为溶剂， 反应 1.5h， 生成 5-tert-Butyl-2,2-dimethyl-1-hydroxylpyrrolidine
  参考文献：
  名称：

  新的 2-取代吡咯啉-N-氧化物：自由基自旋加合物的 EPR 溶剂研究

  摘要：

  制备了 10 个取代的 5,5-二甲基-1-吡咯啉-N-氧化物以及母体氮烯自旋阱（DMPO）：5,5-二甲基-1-吡咯啉-N-氧化物、2,5,5-三甲基-1-吡咯啉-N-氧化物、2-叔丁基-5,5-二甲基-1-吡咯啉-N-氧化物、2-苯基-5,5-二甲基-1-吡咯啉-N-氧化物、2-d5 -苯基-5,5-二甲基-1-吡咯啉-N-氧化物, 2-苯基-5,5-二甲基-1-吡咯啉-N-氧化物-硝酰基-13 C, 2-(4-氟苯基)-5, 5-二甲基-1-吡咯啉-N-氧化物、2-(4-氯苯基)-5,5-二甲基-1-吡咯啉-N-氧化物、2-(4-叔丁基苯基)-5,5-二甲基- 1-吡咯啉-N-氧化物、2-(4-甲基苯基-5,5-二甲基-1-吡咯啉-N-氧化物)和2-(2-甲基苯基)-5,5-二甲基-1-吡咯啉-N-氧化物。获得了这些新型环状硝酮的分析（即 EPR 级）样品，并通过（除其他方法外）1H

  DOI：

  10.1002/mrc.1260321203

文献信息

• BLACK D. S. C.; BOSCACCI A. B., AUSTRAL. J. CHEM. <AJCH-AS>, 1976, 29, NO 11, 2511-2524
  作者：BLACK D. S. C.、 BOSCACCI A. B.

  DOI：——

  日期：——
• Steric effects on regioselectivity in 1.3-Dipolar cycloaddition of C,N-dialyl nitrones with acceptor-substituted alkynes
  作者：Hans Günter Aurich、Michael Franzke、Hans Peter Kesselheim、Markus Rohr

  DOI：10.1016/s0040-4020(01)88127-8

  日期：——

  The 1.3 dipolar cycloaddition of alkynes 4-6 with acyclic nitrones 1-3, 23 and 24 as well as with cyclic nitrones 27 is studied. As was found for the reaction of the aldonitrones 1-3 an increased portion of 5-regioisomers is formed with increasing steric demand of either of the two substituents, the C-alkyl substituent R2 and the N-alkyl substituent R1. Thus the conclusion is drawn that cycloaddition of 1-3 proceeds not only via transition states arising from Z-nitrones but also via transition states developing from E-nitrones, although in the ground-state the Z-isomer is favored to a considerable extent. In this context steric destabilization of the transition states is discussed qualitatively.
• New 2-substituted pyrroline-N-oxides: An EPR solvent study of the radical spin adducts
  作者：Edward G. Janzen、Yong-Kang Zhang、D. Lawrence Haire

  DOI：10.1002/mrc.1260321203

  日期：1994.12

  water) were measured and the solvent effect on these parameters was evaluated. It was found that for the various 2‐substituted DMPO‐type spin adducts both the nitrogen and β‐hydrogen EPR hyperfine splittings correlated linearly (r2 ⩾ 0.90) with typical solvent polarity parameters such as ET(30). The correlation between the nitrogen and β‐hydrogen hyperfine splitting constants were even more linear (r2

  制备了 10 个取代的 5,5-二甲基-1-吡咯啉-N-氧化物以及母体氮烯自旋阱（DMPO）：5,5-二甲基-1-吡咯啉-N-氧化物、2,5,5-三甲基-1-吡咯啉-N-氧化物、2-叔丁基-5,5-二甲基-1-吡咯啉-N-氧化物、2-苯基-5,5-二甲基-1-吡咯啉-N-氧化物、2-d5 -苯基-5,5-二甲基-1-吡咯啉-N-氧化物, 2-苯基-5,5-二甲基-1-吡咯啉-N-氧化物-硝酰基-13 C, 2-(4-氟苯基)-5, 5-二甲基-1-吡咯啉-N-氧化物、2-(4-氯苯基)-5,5-二甲基-1-吡咯啉-N-氧化物、2-(4-叔丁基苯基)-5,5-二甲基- 1-吡咯啉-N-氧化物、2-(4-甲基苯基-5,5-二甲基-1-吡咯啉-N-氧化物)和2-(2-甲基苯基)-5,5-二甲基-1-吡咯啉-N-氧化物。获得了这些新型环状硝酮的分析（即 EPR 级）样品，并通过（除其他方法外）1H