N-甲基-2-[(4-甲基苯基)硫基]乙胺 | 115335-16-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: N-甲基-2-[(4-甲基苯基)硫基]乙胺
• 英文名称: N-methyl-2-<(4-methylphenyl)thio>ethanamine
• 英文别名: N-Methyl-2-[(4-methylphenyl)thio]ethanamine；N-methyl-2-(4-methylphenyl)sulfanylethanamine
• CAS: 115335-16-5
• 化学式: C₁₀H₁₅NS
• mdl: MFCD08691993
• 分子量: 181.302
• InChiKey: OKXZTCFMGIUXTB-UHFFFAOYSA-N

物化性质

• 沸点：
  273.7±23.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  S-1,1'-联-2-萘酚 、 N-甲基-2-[(4-甲基苯基)硫基]乙胺 在 三乙胺 、 三氯化磷 作用下， 以 甲苯 、 四氢呋喃 为溶剂， 以49%的产率得到(3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-methyl-(2-p-tolylsulfanyl-ethyl)-amine
  参考文献：
  名称：

  Design and synthesis of new bidentate phosphoramidite ligands for enantioselective copper-catalyzed conjugate addition of diethylzinc to enones

  摘要：

  Several thioaryl- and phosphino-phosphoramidite ligands have been synthesized from commercially available beta-aminoalcohols. This new family of bidentate ligands are highly active in the enantioselective copper-catalyzed conjugate addition of diethylzinc to both cyclic and acyclic enones showing moderate to good enantiomeric excesses of up to 81%. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.029
• 作为产物：
  描述：

  (2-p-Tolylsulfanyl-ethyl)-carbamic acid tert-butyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到N-甲基-2-[(4-甲基苯基)硫基]乙胺
  参考文献：
  名称：

  Design and synthesis of new bidentate phosphoramidite ligands for enantioselective copper-catalyzed conjugate addition of diethylzinc to enones

  摘要：

  Several thioaryl- and phosphino-phosphoramidite ligands have been synthesized from commercially available beta-aminoalcohols. This new family of bidentate ligands are highly active in the enantioselective copper-catalyzed conjugate addition of diethylzinc to both cyclic and acyclic enones showing moderate to good enantiomeric excesses of up to 81%. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.029

文献信息

• The use of 2-oxazolidinones as latent aziridine equivalents. 2. Aminoethylation of aromatic amines, phenols, and thiophenols
  作者：Graham S. Poindexter、Donald A. Owens、Peter L. Dolan、Edmund Woo

  DOI：10.1021/jo00049a037

  日期：1992.11

  The utility of 2-oxazolidinones 1 as latent, carboxylated aziridine functionalities was examined. Reaction of 2-oxazolidinone (1a), 3-methyl-2-oxazolidinone (1b), 3-(phenylmethyl)-2-oxazolidinone (1c), 3-phenyl-2-oxazolidinone (1d), 4,4-dimethyl-2-oxazolidinone (1e), and 5-ethyl-2-oxazolidinone (1f) with aromatic amine salts, phenol, or thiophenols at elevated temperatures (> 130-degrees-C) afforded aminoethylated adducts. The aminoethylation occurred with concomitant loss of carbon dioxide to furnish variously substituted N-aryl-1,2-ethanediamines 4, 1-(2-phenoxyethyl)-2-imidazolidinone (8), or 2-(arylthio)ethanamines 9 on reactions of 1 with aromatic amine salts, phenol, and thiophenols, respectively. Imidazolidinone 8 is believed to be a secondary reaction product resulting from the condensation of the initially formed 2-phenoxyethanamine with starting oxazolidinone 1a. The aminoethylation reaction did not proceed with aliphatic amine hydrochlorides or alkyl mercaptans. Preliminary mechanistic pathways for these ring openings were also investigated employing a specific, C-5 deuterium-labeled oxazolidinone 1b-d2. Ring-opening experiments of 1b-d2 with N-methylaniline hydrochloride suggest reaction can occur through either a dioxazolinium 5 and/or an aziridinium 6 intermediate. In contrast, reaction of 1b-d2 with thiophenol suggests ring-opening to proceed only via the dioxazolinium pathway.
• MAJEWSKI, EUGENIUSZ;ANDRUSKI, RYSZARD;ZIMINSKA, ZOFIA;BAL, STANISLAW
  作者：MAJEWSKI, EUGENIUSZ、ANDRUSKI, RYSZARD、ZIMINSKA, ZOFIA、BAL, STANISLAW

  DOI：——

  日期：——
• US8658655B2
  申请人：——

  公开号：US8658655B2

  公开（公告）日：2014-02-25