2-[(4-Dimethylamino-benzyl)-methyl-amino]-ethanol | 151696-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(4-Dimethylamino-benzyl)-methyl-amino]-ethanol
• 英文别名: 2-[[4-(Dimethylamino)benzyl](methyl)amino]ethanol；2-[[4-(dimethylamino)phenyl]methyl-methylamino]ethanol
• CAS: 151696-87-6
• 化学式: C₁₂H₂₀N₂O
• 分子量: 208.304
• InChiKey: PBOYVMOCTSNNAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(4-Dimethylamino-benzyl)-methyl-amino]-ethanol 在 铜 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 18.0h， 生成 3-Acetyl-3-(4-(N,N-dimethylamino)benzyl)-4-methylmorpholin-2-one
  参考文献：
  名称：

  Applications of Stevens [1,2]-Shifts of Cyclic Ammonium Ylides. A Route to Morpholin-2-ones

  摘要：

  2-(N,N-Dialkylamino)ethyl diazoacetoacetates 2 were prepared in two steps from readily available ethanolamines 1. When heated in the presence of catalytic Cu, the substrates cleanly formed morpholinones 3, presumably via the intermediacy of copper carbenoids and cyclic ammonium ylides. In most cases involving benzylic or allylic migrating groups, ylide [1,2]-shift occurred in good yield (55-80%). In the case of benzhydryl containing substrate 2g, only dimer 4 was isolated. Simple alkyl groups failed to undergo the rearrangement, with the exception of tert-butyl case 2i, which furnished morpholinone 3i in low yield. Substituted allylic case 2l gave only [1,2]-shift product 3l, with no evidence for competing [2,3]-shift to give 3l'. Diazoacetates 2n-p also underwent conversion to morpholinones 3n-p in 19-64% yield with Cu(acac)(2) catalysis.

  DOI：

  10.1021/jo00099a041
• 作为产物：
  描述：

  2-(4-(二甲基氨基)苯基)-3-甲基恶唑烷 在 萘 、 lithium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.67h， 生成 2-[(4-Dimethylamino-benzyl)-methyl-amino]-ethanol
  参考文献：
  名称：

  α-氨基取代的芳基甲基锂有机金属化合物的产生和反应性

  摘要：

  开链和环状α - N，N-二烷基氨基取代的苄基烷基醚1a - f的还原裂解，分散有Li金属和催化量的萘在THF中，可以轻松获得各种α- N，N -二烷基氨基取代的苄基锂衍生物。这些有机金属与各种亲电试剂的反应以令人满意的产率提供了预期的产物。

  DOI：

  10.1016/s0040-4020(00)00303-3

文献信息

• Reductive cleavage of N-substituted 2-aryl-1,3-oxazolidines: generation of .alpha.-amino-substituted carbanions
  作者：Ugo Azzena、Giovanni Melloni、Cristina Nigra

  DOI：10.1021/jo00076a033

  日期：1993.11

  The behavior of several N-substituted 2-aryl-1,3-oxazolidines has been investigated under conditions of electron transfer from alkali metals in aprotic solvents. The reduction led to the regioselective cleavage of the benzylic carbon-oxygen bond, with formation of the corresponding N-substituted benzylamino alcohols in good yields. Investigation of the mechanism of this reductive cleavage, with the aid of labeling experiments, showed the intermediate formation of alpha-tertiary amino-substituted carbanions.
• West F. G., Naidu B. N., J. Org. Chem, 59 (1994) N 20, S 6051-6056
  作者：West F. G., Naidu B. N.

  DOI：——

  日期：——
• Applications of Stevens [1,2]-Shifts of Cyclic Ammonium Ylides. A Route to Morpholin-2-ones
  作者：F. G. West、B. N. Naidu

  DOI：10.1021/jo00099a041

  日期：1994.10

  2-(N,N-Dialkylamino)ethyl diazoacetoacetates 2 were prepared in two steps from readily available ethanolamines 1. When heated in the presence of catalytic Cu, the substrates cleanly formed morpholinones 3, presumably via the intermediacy of copper carbenoids and cyclic ammonium ylides. In most cases involving benzylic or allylic migrating groups, ylide [1,2]-shift occurred in good yield (55-80%). In the case of benzhydryl containing substrate 2g, only dimer 4 was isolated. Simple alkyl groups failed to undergo the rearrangement, with the exception of tert-butyl case 2i, which furnished morpholinone 3i in low yield. Substituted allylic case 2l gave only [1,2]-shift product 3l, with no evidence for competing [2,3]-shift to give 3l'. Diazoacetates 2n-p also underwent conversion to morpholinones 3n-p in 19-64% yield with Cu(acac)(2) catalysis.
• Generation and Reactivity of α-Amino-Substituted Arylmethyllithium Organometallics
  作者：Ugo Azzena、Luciano Pilo、Elisabetta Piras

  DOI：10.1016/s0040-4020(00)00303-3

  日期：2000.6

  Reductive cleavage of open chain and cyclic α-N,N-dialkylamino-substituted benzyl alkyl ethers 1a–f with a dispersion of Li metal and a catalytic amount of naphthalene in THF, allowed easy access to a wide array of α-N,N-dialkylamino-substituted benzyllithium derivatives. Reaction of these organometallics with various electrophiles afforded the expected products in satisfactory yields.

  开链和环状α - N，N-二烷基氨基取代的苄基烷基醚1a - f的还原裂解，分散有Li金属和催化量的萘在THF中，可以轻松获得各种α- N，N -二烷基氨基取代的苄基锂衍生物。这些有机金属与各种亲电试剂的反应以令人满意的产率提供了预期的产物。