(-)-2-Methyl-1-[(1S)-1-phenylethyl]-1H-pyrrole | 358340-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (-)-2-Methyl-1-[(1S)-1-phenylethyl]-1H-pyrrole
• 英文别名: 2-methyl-1-[(1S)-1-phenylethyl]-1H-pyrrole；2-methyl-1-[(1S)-1-phenylethyl]pyrrole
• CAS: 358340-68-8
• 化学式: C₁₃H₁₅N
• 分子量: 185.269
• InChiKey: CLZJWJQQDGPSAJ-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (-)-2-Methyl-1-[(1S)-1-phenylethyl]-1H-pyrrole 在 lithium aluminium tetrahydride 、 三氯氧磷 作用下， 以 乙醚 、 正戊烷 、 苯 为溶剂， 反应 82.0h， 生成 (1S,2R)-2-((5-methyl-1-((1S)-1-phenylethyl)-1H-pyrrol-2-yl)methylamino)-1-phenylpropan-1-ol
  参考文献：
  名称：

  Synthesis of novel norephedrine-based chiral ligands with multiple stereogenic centers and their application in enantioselective addition of diethylzinc to aldehyde and chalcone

  摘要：

  Novel norephedrine-based chiral ligands with multiple stereogenic centers were conveniently prepared from norephedrine and N-substituted pyrrole. These novel chiral ligands were used to catalyze the enantioselective addition of diethylzinc to aldehydes and to chalcone in high yields and with good to high enantioselectivities. The absolute configuration of products was found to be affected by the stereogenic centers on the norephedrine part of the novel chiral ligands. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.005
• 作为产物：
  描述：

  2-甲基吡咯 、 (S)-(-)- α-甲基苄胺 在 indium(III) tris[bis(trifluoromethanesulfonyl)amide] 作用下， 以 1,4-二氧六环 为溶剂， 反应 40.0h， 以73%的产率得到(-)-2-Methyl-1-[(1S)-1-phenylethyl]-1H-pyrrole
  参考文献：
  名称：

  吡咯与胺的铟催化形式N-芳基化和N-烷基化

  摘要：

  在铟路易斯酸催化下，N-未取代吡咯的氮原子被伯胺的氮原子取代，从而产生N-芳基和N-烷基吡咯。这种将碳骨架正式引入吡咯氮原子的系统显示出独特的选择性：即使在类似的H-N（吲哚基）部分共存时，只有H-N（吡咯基）单元也会经历N-芳基化和N-烷基化。并且芳基-卤素键保持完整。这些明显不同于典型的方法，这取决于以有机卤化物为底物的CN（吡咯基）键形成反应。从吡咯N-保护-脱保护化学的观点来看，值得注意的是，吡咯氮原子上的甲基可以被除去，尽管是正式的方式。

  DOI：

  10.1002/adsc.201600656

文献信息

• Conversion of homochiral amines, β-amino alcohols and α-amino acids to their chiral 2-substituted pyrrole derivatives
  作者：Ayhan S. Demir、Idris M. Akhmedov、Özge Şeşenoglu、Onur Alptürk、Sinem Apaydın、Zuhal Gerçek、Nezire Ibrahimzade

  DOI：10.1039/b008317h

  日期：——

  The conversion of the amino group of chiral amines, amino alcohols, amino acids and their esters into chiral 2-substituted pyrrole derivatives with various halogeno enones is described. The conversion works in good yield and without racemization. The synthesis of 2-phenylpyrrole derivatives was possible with amino alcohols but not with amino acids or their esters.

  介绍了将手性胺、氨基醇、氨基酸及其酯的氨基基团转化为具有各种卤代烯酮的手性2-取代吡咯衍生物的方法。该转化在良好产率下进行，且不会发生消旋化。氨基醇能够合成2-苯基吡咯衍生物，而氨基酸或其酯则不能。
• Metal Triflates-Catalyzed Conjugate Addition of Homochiral Pyrroles to α,β-Unsaturated Esters
  作者：Canan Ünaleroglu、Baris Temelli、Ayhan S. Demir

  DOI：10.1055/s-2004-831195

  日期：——

  The Friedel-Crafts reaction of homochiral pyrrole derivatives with α,β-unsaturated esters catalyzed by metal triflates furnished conjugate addition products. The best yields were obtained by using yttrium triflate and methyl 4-phenyl-2-oxobut-3-enoate (2a). The addition worked regioselectively at C-5 of pyrrole. The diastereoisomers were separated by column chromatography.

  在金属三氟甲磺酸盐催化下，纯手性吡咯衍生物与α,β-不饱和酯发生傅克反应，生成共轭加成产物。使用三氟甲磺酸钇和 4-苯基-2-氧代丁-3-烯酸甲酯 (2a) 获得了最佳产率。该加成在吡咯的 C-5 处区域选择性地起作用。通过柱色谱法分离非对映异构体。
• The synthesis of chiral 5-methylene pyrrol-2(5H)-ones via photooxygenation of homochiral 2-methylpyrrole derivatives
  作者：Ayhan S. Demir、Feray Aydogan、Idris M. Akhmedov

  DOI：10.1016/s0957-4166(02)00140-4

  日期：2002.4

  Homochiral 2-methylpyrrole derivatives are synthesized in high yields starting from chiral amines, amino alcohols and amino acid esters. The photooxygenation of these pyrrole derivatives in the presence of a photosensitiser furnishes the corresponding alpha,beta,gamma,delta-unsaturated gamma-lactams as the major products in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of novel norephedrine-based chiral ligands with multiple stereogenic centers and their application in enantioselective addition of diethylzinc to aldehyde and chalcone
  作者：Canan Unaleroglu、A. Ebru Aydin、Ayhan S. Demir

  DOI：10.1016/j.tetasy.2006.02.005

  日期：2006.3

  Novel norephedrine-based chiral ligands with multiple stereogenic centers were conveniently prepared from norephedrine and N-substituted pyrrole. These novel chiral ligands were used to catalyze the enantioselective addition of diethylzinc to aldehydes and to chalcone in high yields and with good to high enantioselectivities. The absolute configuration of products was found to be affected by the stereogenic centers on the norephedrine part of the novel chiral ligands. (c) 2006 Elsevier Ltd. All rights reserved.
• Indium-Catalyzed Formal N-Arylation and N-Alkylation of Pyrroles with Amines
  作者：Kyohei Yonekura、Kenji Oki、Teruhisa Tsuchimoto

  DOI：10.1002/adsc.201600656

  日期：2016.9.15

  indium Lewis acid catalysis, a nitrogen atom of N‐unsubstituted pyrroles was replaced with a nitrogen atom of primary amines, thereby producing N‐aryl‐ and N‐alkylpyrroles. This system formally introducing such carbon frameworks to the pyrrole nitrogen atom shows unique selectivity: only the H−N(pyrrolyl) unit undergoes the N‐arylation and N‐alkylation even in the coexistence of a similar H−N(indolyl)

  在铟路易斯酸催化下，N-未取代吡咯的氮原子被伯胺的氮原子取代，从而产生N-芳基和N-烷基吡咯。这种将碳骨架正式引入吡咯氮原子的系统显示出独特的选择性：即使在类似的H-N（吲哚基）部分共存时，只有H-N（吡咯基）单元也会经历N-芳基化和N-烷基化。并且芳基-卤素键保持完整。这些明显不同于典型的方法，这取决于以有机卤化物为底物的CN（吡咯基）键形成反应。从吡咯N-保护-脱保护化学的观点来看，值得注意的是，吡咯氮原子上的甲基可以被除去，尽管是正式的方式。