N-thioacetyl-β-(3,4-dimethoxyphenyl)-ethylamine | 91564-56-6

• 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: N-thioacetyl-β-(3,4-dimethoxyphenyl)-ethylamine
• 英文别名: Ethanethioamide, N-[2-(3,4-dimethoxyphenyl)ethyl]-；N-[2-(3,4-dimethoxyphenyl)ethyl]ethanethioamide
• CAS: 91564-56-6
• 化学式: C₁₂H₁₇NO₂S
• 分子量: 239.338
• InChiKey: UDMBOSTYDIEKFC-UHFFFAOYSA-N

物化性质

• 熔点：
  100-102 °C
• 沸点：
  350.8±52.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-thioacetyl-β-(3,4-dimethoxyphenyl)-ethylamine 在 镍 作用下， 生成 2-乙酰基-6,7-二甲氧基-1-亚甲基-1,2,3,4-四氢异喹啉
  参考文献：
  名称：

  π-Cyclization reactions of thio N-acyliminium ions for heterocyclic synthesis

  摘要：

  Thio N-acyliminium ions are readily generated from the reaction of thioamides with bromoacetyl chloride. In the presence of tethered pi-nucleophiles, cyclization occurs to give S,N-acetals which can be further converted into various alkaloid skeletons. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00902-2
• 作为产物：
  描述：

  N-[2-(3,4-二甲氧基苯基)乙基]苯甲酰胺 在 劳森试剂 、 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.25h， 生成 N-thioacetyl-β-(3,4-dimethoxyphenyl)-ethylamine
  参考文献：
  名称：

  Lete, Esther; Collado, M. Isabel; Sotomayor, Nuria, Journal of Heterocyclic Chemistry, 1995, vol. 32, # 6, p. 1751 - 1758

  摘要：

  DOI：

文献信息

• Synthesis and spectroscopic studies of some hydrogenated thiazolo[2,3- a ]isoquinolines
  作者：Maria D Rozwadowska、Agnieszka Sulima

  DOI：10.1016/s0040-4020(01)00224-1

  日期：2001.4

  4-dihydroisoquinoline derivatives under the action of α-mercapto alkanoic acids or ethylene sulfide, respectively. In the synthesis of compounds 2 and 5 isothiocarbostril (13) and N-thioacetyl-β-phenylethylamine derivatives (14), respectively, were also used as substrates and treated with bromoacetic acid derivatives. Spectral characteristics (IR, 1H, 13C NMR and MS) of compounds 1–12 are presented.

  二氢-5- ħ -噻唑并[2,3-一个]异喹啉酮（1 - 6）和四氢-5- ħ -噻唑并[2,3一]异喹啉（7 - 12）已经从下3,4-二氢异喹啉衍生物制备α-巯基链烷酸或亚乙基硫的作用。在化合物2和5的合成中，异硫脲化合物（13）和N-硫代乙酰基-β-苯乙胺衍生物（14）也分别用作底物，并用溴乙酸衍生物处理。光谱特性（IR，1 H，给出了化合物1 – 12的13 C NMR和MS）。
• A One-Pot Bicycloannulation Method for the Synthesis of Tetrahydroisoquinoline Systems
  作者：Albert Padwa、L. Scott Beall、Todd M. Heidelbaugh、Bing Liu、Scott M. Sheehan

  DOI：10.1021/jo991742h

  日期：2000.5.1

  A highly effective method for the synthesis of the core indolo[2,3-a]quinolizidine skeleton found in yohimbine is described. The reaction of N-monosubstituted thioamides with bromoalkenoyl chlorides furnishes thioisomunchnones as transient 1,3-dipoles that undergo ready intramolecular cycloaddition across the tethered pi-bond to give thio-bicycloannulated products in a one-pot operation. The stereochemical outcome of the intramolecular reaction is the consequence of an endo cycloaddition of the neighboring-bond across the transient thioisomunchnone dipole. A major limitation of the method is that when a hydrogen is present in the alpha-position of the thioamide the initially formed thio-N-acyliminium ion undergoes proton loss to produce a S ,N-ketene acetal at a faster rate than dipole formation. Treatment of tetrahydro-beta-carboline-1-thione with 2-bromooct-7-enoyl chloride followed by reductive removal of sulfur from the cycloadduct resulted in the formation of (+/-)-alloyahimbanone. Attempts to cycloadd the thioisomunchnone dipole across several nucleophilic-bonds failed, and instead, products derived from cyclization of the pi-bond onto the initially formed thio-N-acyliminium ion were formed. The resulting N,S-ketals were further converted into several tetrahydroisoquinoline alkaloids in good yield.