1,2,3,4-tetrahydro-2-methylpyridine-1-carboxylic acid tert-butyl ester | 1257080-98-0

• 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: 1,2,3,4-tetrahydro-2-methylpyridine-1-carboxylic acid tert-butyl ester
• 英文别名: 1-Boc-2-methyl-1,2,3,4-tetrahydro-pyridine；tert-butyl 2-methyl-3,4-dihydro-2H-pyridine-1-carboxylate
• CAS: 1257080-98-0
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: RDLOVGLKQIICMT-UHFFFAOYSA-N

物化性质

• 沸点：
  264.7±23.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-2-methylpyridine-1-carboxylic acid tert-butyl ester 、 2-吡啶硼酸 在 [RhCl2(p-cymene)]2 、 copper(II) bis(trifluoromethanesulfonate) 、 silver(l) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以68%的产率得到
  参考文献：
  名称：

  钌催化的，杂原子导向的α-C–H活化/环状酰胺与硼酸的交叉偶联对（杂）芳基和烯基脱氢吡咯烷，脱氢哌啶和氮杂环丙烷进行区域控制的合成†

  摘要：

  描述了通过环酰胺的中间体合成α-芳基和烯基吡咯烷-，哌啶-和氮杂环庚烷衍生物。理想的结果是通过钌催化的，位点选择性的sp 2 C H活化/与芳基和烯基硼酸交叉偶联而实现的。区域选择性（α-SP 2 VS。α-SP 3 VS。β-SP 2 C-H官能化）是通过SP之间的速率差支配2和SP 3的钌金属和之间C-H活化和必要性螯合羰基导向基团。

  DOI：

  10.1039/c5ob02263k
• 作为产物：
  描述：

  Tert-butyl 2-methoxy-6-methylpiperidine-1-carboxylate 在 silica gel 作用下， 生成 1,2,3,4-tetrahydro-2-methylpyridine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  High regioselectivity in electrochemical α-methoxylation of N-protected cyclic amines

  摘要：

  N-Protecting groups of alpha-substituted cyclic amines strongly affected the regioselectivity in electrochemical methoxylation of these compounds. Namely, N-acyl derivatives were transformed into alpha'-methoxylated compounds, while N-cyano derivatives changed into alpha-methoxylated derivatives. Furthermore, Lewis acid catalyzed nucleophilic substitution of the alpha-methoxylated compounds protected with cyano group afforded alpha,alpha-disubstituted cyclic amines. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.060

文献信息

• High regioselectivity in electrochemical α-methoxylation of N-protected cyclic amines
  作者：Samuel S. Libendi、Yosuke Demizu、Yoshihiro Matsumura、Osamu Onomura

  DOI：10.1016/j.tet.2008.02.060

  日期：2008.4

  N-Protecting groups of alpha-substituted cyclic amines strongly affected the regioselectivity in electrochemical methoxylation of these compounds. Namely, N-acyl derivatives were transformed into alpha'-methoxylated compounds, while N-cyano derivatives changed into alpha-methoxylated derivatives. Furthermore, Lewis acid catalyzed nucleophilic substitution of the alpha-methoxylated compounds protected with cyano group afforded alpha,alpha-disubstituted cyclic amines. (c) 2008 Elsevier Ltd. All rights reserved.
• Regiocontrolled synthesis of (hetero)aryl and alkenyl dehydropyrrolidines, dehydropiperidines and azepenes by Ru-catalyzed, heteroatom-directed α-C–H activation/cross-coupling of cyclic enamides with boronic acids
  作者：Timothy K. Beng、Spencer Langevin、Hannah Braunstein、Monique Khim

  DOI：10.1039/c5ob02263k

  日期：——

  The synthesis of α-aryl and alkenyl pyrrolidine-, piperidine-, and azepane derivatives, through the intermediacy of cyclic enamides is described. The desired outcome is achieved through ruthenium-catalyzed, site-selective sp2 C–H activation/cross-coupling with aryl and alkenyl boronic acids. The regioselectivity (α-sp2vs. α-sp3vs. β-sp2 C–H functionalization) is governed by the rate differences between

  描述了通过环酰胺的中间体合成α-芳基和烯基吡咯烷-，哌啶-和氮杂环庚烷衍生物。理想的结果是通过钌催化的，位点选择性的sp 2 C H活化/与芳基和烯基硼酸交叉偶联而实现的。区域选择性（α-SP 2 VS。α-SP 3 VS。β-SP 2 C-H官能化）是通过SP之间的速率差支配2和SP 3的钌金属和之间C-H活化和必要性螯合羰基导向基团。