N-cinnamyl-8-aminomenthol | 235093-79-5

• 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-cinnamyl-8-aminomenthol
• 英文别名: (1R,2S,5R)-5-methyl-2-[2-[[(E)-3-phenylprop-2-enyl]amino]propan-2-yl]cyclohexan-1-ol
• CAS: 235093-79-5
• 化学式: C₁₉H₂₉NO
• 分子量: 287.445
• InChiKey: PLFNAZNODGIUJZ-JZPQVBBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-cinnamyl-8-aminomenthol 以 甲苯 为溶剂， 反应 300.0h， 生成 (1R,2S,5R)-5-Methyl-2-[1-methyl-1-((1R,2R,5R,6R,7S)-2-methyl-6-phenyl-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]dec-8-en-3-yl)-ethyl]-cyclohexanol
  参考文献：
  名称：

  对映体纯高取代四氢环氧异二氢吲哚的短非对映选择性合成

  摘要：

  描述了衍生自 (-)-氨基薄荷醇的 3-烯丙基-2-呋喃基-或 3-糠基-2-乙烯基取代的手性全氢-1,3-苯并恶嗪的非对映选择性分子内 Diels-Alder 反应。[4 + 2]...

  DOI：

  10.1021/jo991544q
• 作为产物：
  描述：

  (1R,2S,5R)-5-methyl-2-<1-methyl-1-(benzylamino)ethyl>cyclohexan-1-ol 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、1.01 MPa 条件下， 反应 48.0h， 生成 N-cinnamyl-8-aminomenthol
  参考文献：
  名称：

  Regio- and Stereoselective 5-exo Radical Cyclizations on a Chiral Perhydro-1,3-benzoxazine Moiety. An Access to Enantiopure 3-Alkylpyrrolidines

  摘要：

  Both enantiomers of chiral, nonracemic S-alkyl-substituted pyrolidines are prepared by diastereoselective 5-exo-trig cyclization on (-)-8-aminomenthol-derived perhydro-1,3-benzoxazines used as chiral auxiliaries, followed by elimination of the menthol appendage. The diastereoselective radical cyclization is promoted by tributyltin hydride and occurs on a 3-aza-5-hexenyl-type radical, leading to five-membered rings in high yield. The stereocontrol of the cyclization is strongly influenced by 1,3-allylic strain so that an appropriate substitution pattern on the olefin-acceptor and the presence of a vicinal stereocenter are crucial for achieving good diastereoselectivity. The enantiopure pyrrolidines are obtained in three steps with concomitant recovering of the starting (+)-pulegone auxiliary.

  DOI：

  10.1021/jo9816921

文献信息

• A Novel Synthesis of Enantiopure Octahydropyrrolo[3,4-b]pyrroles by Intramolecular [3 + 2] Dipolar Cycloaddition on Chiral Perhydro-1,3-benzoxazines
  作者：Rafael Pedrosa、Celia Andrés、Laura de las Heras、Javier Nieto

  DOI：10.1021/ol0261377

  日期：2002.7.1

  [GRAPHIC]Condensation of N-substituted glycines with chiral 3-allyl-2-formyl perhydro-1,3-benzoxazines forms an azomethine ylide that cyclizes to give octahydropyrrolo[3,4-b]pyrrole derivatives. The [3 + 2] dipolar cycloadditions are stereoespecific leading to a single diastereoisomer. The chemical yields are dependent on the reaction temperature and the presence or absence of a base.