2,2,2-trichloro-N-[1-(2,4,6-trimethylphenyl)allyl]acetamide | 1332888-00-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,2,2-trichloro-N-[1-(2,4,6-trimethylphenyl)allyl]acetamide
• CAS: 1332888-00-2
• 化学式: C₁₄H₁₆Cl₃NO
• 分子量: 320.646
• InChiKey: NPOCMOFJIDAYAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloro-N-[1-(2,4,6-trimethylphenyl)allyl]acetamide 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以87%的产率得到1-(2,4,6-trimethylphenyl)prop-2-en-1-amine
  参考文献：
  名称：

  An efficient enzymatic approach to (S)-1-aryl-allylamines

  摘要：

  A range of 1-aryl-allylamines were prepared in moderate to excellent enantioselectivity (ee 63.5%-> 99.9%) using lipase B from a Candida antarctica catalyzed resolution of racemic amines. This is the first time that CaLB has been used for the resolution of 1-aryl-allylamines. Racemic amines were prepared starting from aromatic aldehydes with a [3,3]-sigmatropic rearrangement of the acyclic imidates as the key step followed by trichloroacetamidate hydrolysis. Aldehydes were converted into acrylic esters using Knoevenagel reaction. After reduction, the corresponding alcohols were used for the preparation of trichloroacetimidates, which were then used in an Overman rearrangement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.004
• 作为产物：
  描述：

  (E)-3-mesitylprop-2-en-1-ol 在 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 24.25h， 生成 2,2,2-trichloro-N-[1-(2,4,6-trimethylphenyl)allyl]acetamide
  参考文献：
  名称：

  An efficient enzymatic approach to (S)-1-aryl-allylamines

  摘要：

  A range of 1-aryl-allylamines were prepared in moderate to excellent enantioselectivity (ee 63.5%-> 99.9%) using lipase B from a Candida antarctica catalyzed resolution of racemic amines. This is the first time that CaLB has been used for the resolution of 1-aryl-allylamines. Racemic amines were prepared starting from aromatic aldehydes with a [3,3]-sigmatropic rearrangement of the acyclic imidates as the key step followed by trichloroacetamidate hydrolysis. Aldehydes were converted into acrylic esters using Knoevenagel reaction. After reduction, the corresponding alcohols were used for the preparation of trichloroacetimidates, which were then used in an Overman rearrangement. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.004

文献信息

• Determination of the Absolute Configuration of (<i>S</i> )-<i>N</i> -(1-Aryl-allyl)-3,5-dinitrobenzamides and Their Elution Order on Brush-Type Chiral Stationary Phases
  作者：Anamarija Knežević、Jurica Novak、Gennaro Pescitelli、Vladimir Vinković

  DOI：10.1002/ejoc.201800346

  日期：2018.8.7

  (S‐DNBs) was prepared using enzymatic resolution and chiral chromatography. Enzymatic resolution of corresponding 1‐aryl‐allylamines using Candida antarctica lipase B (CaLB) was efficient for amines with no steric hindrance near the stereogenic center and S‐DNB amides were prepared by acylation of the obtained S‐amine. When steric effects interrupted enzymatic resolution, racemic DNB amides were resolved

  使用酶拆分和手性色谱法制备了一系列 10 种对映体纯 (S)-N-(1-芳基-烯丙基)-3, 5-二硝基苯甲酰胺 (S-DNB)。使用南极念珠菌脂肪酶 B (CaLB) 对相应的 1-芳基烯丙胺进行酶促拆分对于在立体中心附近没有空间位阻的胺是有效的，并且通过酰化获得的 S-胺制备 S-DNB 酰胺。当空间效应中断酶促拆分时，使用我们实验室开发的刷式手性柱 (CSP-A) 拆分外消旋 DNB 酰胺。先前报道的 CaLB 在胺的动力学拆分中的行为被认为是确定绝对构型 (AC) 的起点。使用制备的 DNB 酰胺在 CSP-A 和商业 Whelk-O1 柱上的洗脱顺序并与（S）-胺酰化后获得的 DNB 酰胺进行比较，预计制备的 S-DNB 酰胺的 AC。实验电子圆二色性 (ECD) 光谱与通过代表性化合物的构象分析和 ECD 计算获得的光谱之间的比较使我们能够验证制备的 DNB 酰胺的 AC。