N-benzyl-2-(1H-indol-3-yl)-N-methylethan-1-amine | 14120-99-1

• 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-2-(1H-indol-3-yl)-N-methylethan-1-amine
• 英文别名: N-benzyl-2-(1H-indol-3-yl)-N-methylethanamine
• CAS: 14120-99-1
• 化学式: C₁₈H₂₀N₂
• 分子量: 264.37
• InChiKey: SULYXIDYHIHCJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  429.009±33.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.122±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-(1H-indol-3-yl)-N-methylethan-1-amine 在 aluminum (III) chloride 、 Selectfluor 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 0.5h， 以90%的产率得到3-[2-(N-benzyl-N-methylamino)ethyl]-3-fluoro-2-oxoindole
  参考文献：
  名称：

  通过直接氟化N，N-二烷基类色胺合成3- [2-（N，N-二烷基氨基）乙基] -3-氟代吲哚的简便方法

  摘要：

  已开发出一种合成具有碱性胺基团的3-氟羟吲哚衍生物的实用方法，该方法涉及在路易斯酸存在下，Selectfluor TM介导的N，N-二烷基色胺的氧化氟化。将该方法应用于抗偏头痛药物利扎曲普坦（rizatriptan），得到相应的3-氟羟吲哚，其是潜在的含氟药物候选物。

  DOI：

  10.1016/j.jfluchem.2010.12.014
• 作为产物：
  描述：

  2-(1H-indol-3-yl)-N-methyl-N-benzyl acetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以52 %的产率得到N-benzyl-2-(1H-indol-3-yl)-N-methylethan-1-amine
  参考文献：
  名称：

  [EN] NOVEL BENZYLTRYPTAMINE COMPOUNDS
  [FR] NOUVEAUX COMPOSÉS DE BENZYLTRYPTAMINE

  摘要：

  There is disclosed a compound of Formula (I): and any pharmaceutically acceptable salt or zwitterion thereof; wherein: R is hydrogen, methyl or ethyl; R1is hydrogen or C1-C2alkoxy; R2is methyl or a C2-C4group which may be saturated or unsaturated, branched or linear; and R3, R4, R5and R6each are independently selected from hydrogen, hydroxyl, halogen, methyl optionally substituted with hydroxy, methoxy, ethoxy, and a saturated or unsaturated C2-C3that may be optionally substituted with hydroxyl, with the provisos that: (i) at least two of R4, R5, R6and R7must be hydrogen, and (ii) R3, R4, R5and R6may be selected such that an adjacent pair thereof join to form a ring having at least 5 members. The compound of Formula (I) is believed useful in treating a disease or disorder in a subject which may be alleviated by a 5HT2A agonist (e.g., CNS disorders and one or more symptoms of any one of depression, alcoholism, tobacco addiction, cocaine addiction, inflammation, cluster headache and PTSD in a subject).

  公开号：

  WO2023070228A1

文献信息

• Tandem synthesis of <i>N</i>-methylated tertiary amines <i>via</i> three-component coupling of carbonyl compounds, amines, and methanol
  作者：Ishani Borthakur、Sameer Srivastava、Saloni Kumari、Sabuj Kundu

  DOI：10.1039/d2cc03115a

  日期：——

  An Ir-catalyzed tandem synthesis of various N-methylated tertiary amines from three-component coupling of carbonyl compounds, amines, and methanol following reductive amination/N-methylation is reported for the first time. A wide array of substrates with tolerance of different functional groups was demonstrated. The protocol was extended to the synthesis of N-methyl containing pharmaceutically important

  首次报道了还原胺化/ N-甲基化后由羰基化合物、胺和甲醇的三组分偶联合成各种N-甲基化叔胺的 Ir 催化串联合成。展示了具有不同官能团耐受性的多种底物。该方案扩展到合成含有N-甲基的药学上重要的药物分子。基于各种控制实验和不同的分析技术（如 NMR、IR 和 ESI-MS）提出了可能的催化循环。
• Investigations into the mechanism of lactamization of lactones yielding in a novel route to biologically active tryptamine derivatives
  作者：Michael Decker、Thi Thanh Huyen Nguyen、Jochen Lehmann

  DOI：10.1016/j.tet.2004.03.073

  日期：2004.5

  The mechanism of lactamization of corresponding lactones was investigated by means of gas chromatography and synthesis of possible intermediates as references. Lactones react with amines via the amino acid with subsequent elimination of water to the corresponding lactams. In the first step, also hydroxyamides are in equilibrium with the lactones and amines, respectively, which are not able to form the amide though. This mechanism opens a new approach for the synthesis of N-beta-disubstituted tryptamines. (C) 2004 Elsevier Ltd. All rights reserved.
• A facile procedure for synthesis of 3-[2-(N,N-dialkylamino)ethyl]-3-fluorooxindoles by direct fluorination of N,N-dialkyltryptamines
  作者：Takayuki Seki、Tomoya Fujiwara、Yoshio Takeuchi

  DOI：10.1016/j.jfluchem.2010.12.014

  日期：2011.3

  A practical procedure for the synthesis of 3-fluorooxindole derivatives having basic amine moieties was developed, which involves Selectfluor™-mediated oxidative fluorination of N,N-dialkyltryptamines in the presence of Lewis acid. This procedure was applied to an antimigraine drug, rizatriptan, to afford the corresponding 3-fluorooxindole, which is a potential fluorine-containing drug candidate.

  已开发出一种合成具有碱性胺基团的3-氟羟吲哚衍生物的实用方法，该方法涉及在路易斯酸存在下，Selectfluor TM介导的N，N-二烷基色胺的氧化氟化。将该方法应用于抗偏头痛药物利扎曲普坦（rizatriptan），得到相应的3-氟羟吲哚，其是潜在的含氟药物候选物。
• [EN] NOVEL BENZYLTRYPTAMINE COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS DE BENZYLTRYPTAMINE
  申请人：[en]REUNION NEUROSCIENCE CANADA INC.

  公开号：WO2023070228A1

  公开（公告）日：2023-05-04

  There is disclosed a compound of Formula (I): and any pharmaceutically acceptable salt or zwitterion thereof; wherein: R is hydrogen, methyl or ethyl; R1is hydrogen or C1-C2alkoxy; R2is methyl or a C2-C4group which may be saturated or unsaturated, branched or linear; and R3, R4, R5and R6each are independently selected from hydrogen, hydroxyl, halogen, methyl optionally substituted with hydroxy, methoxy, ethoxy, and a saturated or unsaturated C2-C3that may be optionally substituted with hydroxyl, with the provisos that: (i) at least two of R4, R5, R6and R7must be hydrogen, and (ii) R3, R4, R5and R6may be selected such that an adjacent pair thereof join to form a ring having at least 5 members. The compound of Formula (I) is believed useful in treating a disease or disorder in a subject which may be alleviated by a 5HT2A agonist (e.g., CNS disorders and one or more symptoms of any one of depression, alcoholism, tobacco addiction, cocaine addiction, inflammation, cluster headache and PTSD in a subject).