2-Methoxycarbonylmethyl-6-methyl-2,3,4,5-tetrahydropyridine 1-oxide | 113410-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-Methoxycarbonylmethyl-6-methyl-2,3,4,5-tetrahydropyridine 1-oxide
• 英文别名: Methyl 2-(6-methyl-1-oxido-2,3,4,5-tetrahydropyridin-1-ium-2-yl)acetate
• CAS: 113410-53-0
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: PLGLMAYLUBWJMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methoxycarbonylmethyl-6-methyl-2,3,4,5-tetrahydropyridine 1-oxide 以 溶剂黄146 、 甲苯 为溶剂， 反应 9.0h， 生成 [(3bS,7S)-1-(4-Chloro-phenyl)-3,3b-dimethyl-8-oxo-3b,4,5,6,7,8-hexahydro-1H-1,2,7a-triaza-cyclopenta[a]inden-7-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Bowman, W. Russell; Davies, Roy V.; Slawin, Alexandra M. Z., Journal of the Chemical Society. Perkin transactions I, 1997, # 2, p. 155 - 161

  摘要：

  DOI：
• 作为产物：
  描述：

  5-oxohexanal 在 盐酸羟胺 、 sodium acetate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 2-Methoxycarbonylmethyl-6-methyl-2,3,4,5-tetrahydropyridine 1-oxide
  参考文献：
  名称：

  X = Y - ZH systems as potential 1,3-dipoles part 35. Generation of nitrones from oximes. Class 3 processes. Tandem intramolecular michael addition (1,3-azaprotio cyclotransfer) - intermolecular 1,3-dipolar cycloaddition reactions.

  摘要：

  Aldoximes and ketoximes possessing gamma- or delta-alkenyl substituents undergo thermal conversion to 5- and 6- membered cyclic nitrones via a 1,3-azaprotio cyclotransfer, a 2n + 2-sigma + 2-pi concerted process, rather than a Michael addition. The reactions can be performed as a tandem nitrone formation-cycloaddition sequence or, if required, the intermediate nitrones can be isolated. The cycloadditions usually proceed via an exo-transition state and show both regio- and diastereofacial-specificity. Preliminary attempts at chiral induction via a menthyl auxiliary are reported.

  DOI：

  10.1016/s0040-4020(01)89883-5

文献信息

• Tandem intramolecular Michael addition and 1,3-dipolar cycloaddition reactions of oximes; versatile new carbon–carbon bond forming methodology
  作者：Paul Armstrong、Ronald Grigg、Sivagnanasundram Surendrakumar、William J. Warnock

  DOI：10.1039/c39870001327

  日期：——

  Oximes undergo intramolecular Michael addition to proximate electronegative alkenes, generating cyclic nitrones which can be trapped inter- and intra-molecularly in 1,3-dipolar cycloaddition reactions taking place either separately or in tandem.

  肟经过分子内迈克尔加成反应，形成邻近的负电性烯烃，生成环状硝酮，可被分子间和分子内捕获在分别或串联发生的1,3-偶极环加成反应中。
• ARMSTRONG, PAUL;GRIGG, RONALD;SURENDRAKUMAR, SIVAGNANASUNDRAM;WARNOCK, WI+, J. CHEM. SOC. CHEM. COMMUN.,(1987) N 17, 1327-1328
  作者：ARMSTRONG, PAUL、GRIGG, RONALD、SURENDRAKUMAR, SIVAGNANASUNDRAM、WARNOCK, WI+

  DOI：——

  日期：——
• Bowman, W. Russell; Davies, Roy V.; Slawin, Alexandra M. Z., Journal of the Chemical Society. Perkin transactions I, 1997, # 2, p. 155 - 161
  作者：Bowman, W. Russell、Davies, Roy V.、Slawin, Alexandra M. Z.、Sohal, Gian S.、Titman, Roger B.、Wilkins, David J.

  DOI：——

  日期：——
• X = Y - ZH systems as potential 1,3-dipoles part 35. Generation of nitrones from oximes. Class 3 processes. Tandem intramolecular michael addition (1,3-azaprotio cyclotransfer) - intermolecular 1,3-dipolar cycloaddition reactions.
  作者：Ronald Grigg、Jasothara Markandu、Trevor Perrior、Sivagnanasundram Surendrakumar、William J. Warnock

  DOI：10.1016/s0040-4020(01)89883-5

  日期：1992.1

  Aldoximes and ketoximes possessing gamma- or delta-alkenyl substituents undergo thermal conversion to 5- and 6- membered cyclic nitrones via a 1,3-azaprotio cyclotransfer, a 2n + 2-sigma + 2-pi concerted process, rather than a Michael addition. The reactions can be performed as a tandem nitrone formation-cycloaddition sequence or, if required, the intermediate nitrones can be isolated. The cycloadditions usually proceed via an exo-transition state and show both regio- and diastereofacial-specificity. Preliminary attempts at chiral induction via a menthyl auxiliary are reported.