N-benzyl-3-(1H-indol-3-yl)propan-1-amine | 87400-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-benzyl-3-(1H-indol-3-yl)propan-1-amine
• 英文别名: N-benzyl-3-(3-indolyl)propylamine
• CAS: 87400-38-2
• 化学式: C₁₈H₂₀N₂
• mdl: MFCD00421507
• 分子量: 264.37
• InChiKey: LLYSVXLWCQNOSB-UHFFFAOYSA-N

物化性质

• 沸点：
  456.8±33.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-(1H-indol-3-yl)propan-1-amine 在 劳森试剂 、 盐酸 、 sodium hydroxide 、 次氯酸叔丁酯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 22.41h， 生成 methyl 3-benzyl-2-thioxo-2,3,4,5,6,11-hexahydro-1H-azocino[4,5-b]indole-1-carboxylate
  参考文献：
  名称：

  Syntheses of 5a‘-homo-Vinblastine and Congeners Designed to Establish Structural Determinants for Isolation of Atropisomers

  摘要：

  The syntheses of 5a'-homo-vinblastine (3a) and its C-20' methyl congener 62a were achieved. In contrast to vinblastine, these compounds did not allow isolation of atropisomers because of their lower conformational inversion barrier. However, annelation of a six-membered ring to the conformationally mobile D'-piperidine ring provided an isolated atropisomer 81a, which could be converted to its lower energy conformation 65a on heating. The 5a'-homo-vinblastine congeners 3a, 62a, and 65a showed vinblastine-like inhibition of tubulin polymerization and cytotoxicity to L1210 leukemia cells, albeit at lower potency for the latter activity, than that found with the corresponding compounds in the vinblastine series.

  DOI：

  10.1021/jo000249z
• 作为产物：
  描述：

  3-吲哚丙酸 在 lithium aluminium tetrahydride 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 N-benzyl-3-(1H-indol-3-yl)propan-1-amine
  参考文献：
  名称：

  碘化物/ H 2 O 2催化的分子内氧化胺合成3,2'-吡咯烷基磺酰吲哚。

  摘要：

  实现了碘化铵/过氧化氢介导的3-氨基烷基-2-氧吲哚的分子内氧化胺化作用，以中等至高收率提供了相应的3,2'-吡咯烷基磺基螺硫醇及其6-或7-元类似物。该无金属工艺具有非常温和的反应条件，无毒且易于处理的过氧化氢作为清洁氧化剂。

  DOI：

  10.3390/molecules23092265

文献信息

• Syntheses of Strychnine, Norfluorocurarine, Dehydrodesacetylretuline, and Valparicine Enabled by Intramolecular Cycloadditions of Zincke Aldehydes
  作者：David B. C. Martin、Lucas Q. Nguyen、Christopher D. Vanderwal

  DOI：10.1021/jo2020246

  日期：2012.1.6

  base-mediated intramolecular Diels–Alder cycloadditions of tryptamine-derived Zincke aldehydes is described. This important complexity-generating transformation provides the tetracyclic core of many indole monoterpene alkaloids in only three steps from commercially available starting materials and played a key role in short syntheses of norfluorocurarine (five steps), dehydrodesacetylretuline (six steps), valparicine

  描述了由色胺衍生的锌醛的碱基介导的分子内Diels-Alder环加成反应的完整过程。这项重要的复杂性转化过程可从市售起始原料仅三步即可提供许多吲哚单萜生物碱的四环核，并且在正氟尿嘧啶的短合成（五步），脱氢脱乙酰基苯甲酸（六步），瓦尔帕比星（七步）的短合成中发挥了关键作用。 ，和士的宁（六个步骤）。还讨论了该反应的合理机理可能性，产物令人惊讶地容易的二聚化，以及在特定条件下出乎意料的环还原以再生锌酮醛。
• Catalytic Radical Process for Enantioselective Amination of C(sp ³ )−H Bonds
  作者：Chaoqun Li、Kai Lang、Hongjian Lu、Yang Hu、Xin Cui、Lukasz Wojtas、X. Peter Zhang

  DOI：10.1002/anie.201808923

  日期：2018.12.17

  system involving CoII -based metalloradical catalysis is effective in activating sulfamoyl azides for enantioselective radical 1,6-amination of C(sp3 )-H bonds, affording six-membered chiral heterocyclic sulfamides in high yields with excellent enantioselectivities. The CoII -catalyzed C-H amination features an unusual degree of functional-group tolerance and chemoselectivity. The unique reactivity

  一种涉及基于CoII的金属自由基催化的新型催化自由基体系可有效活化氨磺酰叠氮化物，以对C(sp3)-H键进行对映选择性自由基1,6-胺化，以高产率提供具有优异对映选择性的六元手性杂环磺酰胺。CoII 催化的 CH 胺化具有异常程度的官能团耐受性和化学选择性。独特的反应性和立体选择性归因于潜在的逐步自由基途径。所得光学活性环状磺酰胺可以很容易地转化为合成上有用的手性1,3-二胺衍生物，而不损失对映体纯度。
• DURGARYAN, A. K.;MELIK-OGANDZHANYAN, A. S.;POGOSYAN, S. A.;ARZANUNTS, EH.+, ARM. XIM. ZH., 1983, 36, N 5, 317-323
  作者：DURGARYAN, A. K.、MELIK-OGANDZHANYAN, A. S.、POGOSYAN, S. A.、ARZANUNTS, EH.+

  DOI：——

  日期：——
• Syntheses of 5a‘-<i>h</i><i>omo</i>-Vinblastine and Congeners Designed to Establish Structural Determinants for Isolation of Atropisomers
  作者：Martin E. Kuehne、Scott D. Cowen、Feng Xu、Linda S. Borman

  DOI：10.1021/jo000249z

  日期：2001.8.1

  The syntheses of 5a'-homo-vinblastine (3a) and its C-20' methyl congener 62a were achieved. In contrast to vinblastine, these compounds did not allow isolation of atropisomers because of their lower conformational inversion barrier. However, annelation of a six-membered ring to the conformationally mobile D'-piperidine ring provided an isolated atropisomer 81a, which could be converted to its lower energy conformation 65a on heating. The 5a'-homo-vinblastine congeners 3a, 62a, and 65a showed vinblastine-like inhibition of tubulin polymerization and cytotoxicity to L1210 leukemia cells, albeit at lower potency for the latter activity, than that found with the corresponding compounds in the vinblastine series.
• Iodide/H2O2 Catalyzed Intramolecular Oxidative Amination for the Synthesis of 3,2′-Pyrrolidinyl Spirooxindoles
  作者：Yu-Ting Gao、Xiao-Yang Jin、Qi Liu、An-Di Liu、Liang Cheng、Dong Wang、Li Liu

  DOI：10.3390/molecules23092265

  日期：——

  An ammonium iodide/hydrogen peroxide-mediated intramolecular oxidative amination of 3-aminoalkyl-2-oxindoles was achieved, affording the corresponding 3,2'-pyrrolidinyl spirooxindoles and their 6- or 7-membered analogous in moderate to high yields. This metal-free procedure features very mild reaction conditions, non-toxicity and easily handled hydrogen peroxide as a clean oxidant.

  实现了碘化铵/过氧化氢介导的3-氨基烷基-2-氧吲哚的分子内氧化胺化作用，以中等至高收率提供了相应的3,2'-吡咯烷基磺基螺硫醇及其6-或7-元类似物。该无金属工艺具有非常温和的反应条件，无毒且易于处理的过氧化氢作为清洁氧化剂。