2-Deuterio-N-phenylethylamine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-Deuterio-N-phenylethylamine
• 英文别名: N-(2-deuterioethyl)aniline
• 化学式: C₈H₁₁N
• 分子量: 122.174
• InChiKey: OJGMBLNIHDZDGS-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(2-氯乙基)苯胺 生成 2-Deuterio-N-phenylethylamine
  参考文献：
  名称：

  Naphthalene-catalysed reductive opening of aziridines with lithium: A direct preparation of n-lithio-2-lithioalkylamines

  摘要：

  The reductive opening of N-phenylaziridine (1) with an excess of lithium powder in the presence of a catalytic amount (5 molar %) of naphthalene at -78-degrees-C leads to the corresponding N-lithio-2-lithioethylamine (2), which by reaction with different electrophiles (water, deuterium oxide, dimethyl disulphide, pivalaldehyde or cyclohexanone) affords the expected produces 3. The same process applied to N-cyclohexylaziridine fails. the reaction also works with the chiral aziridine 4 yielding the chiral deuteriated amine 5, through the corresponding chiral dianionic intermediate.

  DOI：

  10.1016/0040-4039(93)85032-r

文献信息

• Functionalized Organolithium Compounds by DTBB-Catalyzed Sulfur-Lithium Exchange
  作者：Francisco Foubelo、Ana Gutiérrez、Miguel Yus

  DOI：10.1055/s-1999-3426

  日期：1999.3

  The successive reaction of β- or γ-hydroxy or amino phenyl thioethers (1, 4) with butyllithium and an excess of lithium powder in the presence of a catalytic amount of DTBB in THF at - 78 °C leads to the formation of the corresponding β-γ-functionalized organolithium compounds 2 or 5, respectively, which by treatment with different electrophiles [D2O, t-BuCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO] at temperatures ranging between - 78 °C and room temperature yields, after hydrolysis with water, the expected functionalized alcohols or amines 3 or 6, respectively, in a completely regioselective manner.

  β-或γ-羟基或氨基苯硫醚（1, 4）与丁基锂和过量锂粉在催化量的DTBB存在下，在-78°C的THF中连续反应，分别生成相应的β-γ-功能化有机锂化合物2或5。这些化合物与不同的亲电试剂[D2O, t-BuCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO]在-78°C至室温范围内的温度下处理后，经水解，以完全区域选择性的方式分别得到预期的功能化醇或胺3或6。
• β-Functionalised organolithium compounds through a sulfur-lithium exchange
  作者：Francisco Foubelo、Ana Gutiérrez、Miguel Yus

  DOI：10.1016/s0040-4039(97)01008-3

  日期：1997.7

  The successive reaction of different β-hydroxy or β-amino thioethers 1a-d with n-butyl-lithium and an excess of lithium powder and a catalytic amount of DTBB in THF at −78°C leads to the formation of the corresponding β-functionalised organolithium compounds 2a-d, which by reaction with several electrophiles [D2O, ButCHO, PhCHO, Me2CO, (CH2)5CO] at temperatures ranging between −78 and 20°C yields,

  不同的β-羟基或β-氨基硫醚1a-d与正丁基锂，过量的锂粉和催化量的DTBB在-78°C的THF中连续反应导致形成相应的β-官能化有机锂化合物2A-d ，其通过与亲电子数[d反应2 O，卜吨CHO，苯甲醛中，Me 2 CO，（CH 2）5 CO]在温度范围-78至20℃之间的产率，用水解后水，预期的功能化醇或胺3aa-de（区域选择性）。
• N,2-Dilithioalkylamines from Aziridines by Naphthalene-Catalyzed Reductive Opening. Synthetic Applications
  作者：Juan Almena、Francisco Foubelo、Miguel Yus

  DOI：10.1021/jo00090a044

  日期：1994.6

  The reductive opening of aziridines 1a-c with lithium in the presence of a catalytic amount of naphthalene at -78 degrees C led to the corresponding dianionic intermediates 2a-c, which are stable species under these reaction conditions and react with electrophilic reagents [H2O, D2O, Me(2)S(2), Bu(t)CHO, PhCHO, Me(2)CO, (CH2)(5)CO, (EtO)(2)CO, CH2=CHCO(2)Me, PhCON(CH2)(4), PhCH=NPh, MeI, and CH2=CHCH2Br] to give, after hydrolysis with water, the corresponding difunctionalized compounds 3-5. When the reductive opening and the reaction with electrophiles [H2O, D2O, CH2=CHCH2Br, Me(2)CO, (c-C3H5)(2)CO] were carried out on chiral aziridines 8 and 9, enantiomerically pure difunctionalized compounds 12 were obtained with same stereochemistry, independently of the stereochemistry of diastereomeric starting aziridines 8 and 9.
• Naphthalene-catalysed reductive opening of aziridines with lithium: A direct preparation of n-lithio-2-lithioalkylamines
  作者：Juan Almena、Francisco Foubelo、Miguel Yus

  DOI：10.1016/0040-4039(93)85032-r

  日期：1993.3

  The reductive opening of N-phenylaziridine (1) with an excess of lithium powder in the presence of a catalytic amount (5 molar %) of naphthalene at -78-degrees-C leads to the corresponding N-lithio-2-lithioethylamine (2), which by reaction with different electrophiles (water, deuterium oxide, dimethyl disulphide, pivalaldehyde or cyclohexanone) affords the expected produces 3. The same process applied to N-cyclohexylaziridine fails. the reaction also works with the chiral aziridine 4 yielding the chiral deuteriated amine 5, through the corresponding chiral dianionic intermediate.