N',N'-(Boc)2-tryptamine | 195191-59-4

• 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',N'-(Boc)2-tryptamine
• 英文别名: N¹⁰-(di(tert-butoxycarbonyl))tryptamine；N^b,N^b-di-(tert-butoxycarbonyl)tryptamine；1,3-Bis(1,1-dimethylethyl) 2-[2-(1H-indol-3-yl)ethyl]imidodicarbonate；tert-butyl N-[2-(1H-indol-3-yl)ethyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate
• CAS: 195191-59-4
• 化学式: C₂₀H₂₈N₂O₄
• 分子量: 360.453
• InChiKey: IVGCDZNZSXAXSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N',N'-(Boc)2-tryptamine 在 碳酸氢钠 、 Selectfluor 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 以73%的产率得到
  参考文献：
  名称：

  Synthetic Studies on the Fluorinated Analogs for the Putative Oxindole-Type Metabolites of 5-Halotryptamines

  摘要：

  The suitably protected precursors for direct fluorination, N(b)-Boc di-protected 5-fluorotryptamine (13), N(b)-acetyl-N(b)-Boc protected 5-halotryptamines (15a-c), were treated with Selectfluor (TM) in MeCN/water in the presence of NaHCO(3) to give the corresponding 3-fluorooxindoles 14 and 16a-c in good yields. Removal of the protecting groups of 14 and 16a-c produced (3,5-difluorooxindol-3-yl)ethylamine (8) and N-acetyl-(3-fluoro-5-halooxindol-3-yl)ethylamines (9a-c) in excellent yields, respectively. These compounds are potentially non-epimerizable analogs for the putative metabolites of 5-fluorotryptamine (6) and N(b)-acetyl-5-halotryptamines (7a-c).

  DOI：

  10.3987/com-08-s(d)70
• 作为产物：
  描述：

  N,N-双叔丁氧羰基-N-烯丙胺 在 palladium diacetate 、 三(三苯基膦)羰基氢化铑 、 氢气 、 三苯基膦 、 三(邻甲基苯基)磷 作用下， 以 三乙胺 、 甲苯 、 乙腈 为溶剂， 70.0 ℃ 、2.07 MPa 条件下， 反应 70.0h， 生成 N',N'-(Boc)2-tryptamine
  参考文献：
  名称：

  Indoles from o-Haloanilines:  Syntheses of Tryptamines and Tryptophols via Regioselective Hydroformylation of Functionalized Anilines

  摘要：

  DOI：

  10.1021/jo9711798

文献信息

• Mild Deprotection of<i>tert</i>‐Butyl Carbamates of NH‐Heteroarenes under Basic Conditions
  作者：Manas Chakrabarty、Taraknath Kundu、Yoshihiro Harigaya

  DOI：10.1080/00397910600634480

  日期：2006.6

  Abstract Aqueous methanolic potassium carbonate under reflux has been demonstrated to be a highly effective deprotective agent for the tert‐butyl carbamates of indoles, indazoles, carbazole, thiazoloindole, and pyrrole. The method is a mild one and is particularly expeditious for NH‐heteroarenes bearing electron‐withdrawing groups.

  摘要 回流下的甲醇碳酸钾水溶液已被证明是吲哚、吲唑、咔唑、噻唑并吲哚和吡咯的氨基甲酸叔丁酯的高效脱保护剂。该方法是一种温和的方法，尤其适用于带有吸电子基团的 NH-杂芳烃。
• A Procedure for Transforming Indoles into Indolequinones
  作者：Andrew S. Eastabrook、Christy Wang、Emma K. Davison、Jonathan Sperry

  DOI：10.1021/jo502509s

  日期：2015.1.16

  A procedure that converts a series of structurally diverse, readily available indole derivatives to their corresponding indolequinones is described. The three-step route commences with an iridium catalyzed C-H borylation to give a 7-borylindole that upon oxidationhydrolysis affords the 7-hydroxyindole. Subsequent oxidation provides the indolequinone.
• Palladium-catalyzed synthesis of tryptamines and tryptamine homologues: synthesis of psilocin
  作者：Chunmei Hu、Hua Qin、Yuxin Cui、Yanxing Jia

  DOI：10.1016/j.tet.2009.09.050

  日期：2009.11

  A new Pd-catalyzed method for the synthesis of tryptamines is developed, and its applications to the synthesis of Corey's aspidophytine tryptamine 15 and psilocin 20 are also described. (C) 2009 Elsevier Ltd. All rights reserved.
• Indoles from <i>o</i>-Haloanilines:  Syntheses of Tryptamines and Tryptophols <i>via</i> Regioselective Hydroformylation of Functionalized Anilines
  作者：Yong Dong、Carl A. Busacca

  DOI：10.1021/jo9711798

  日期：1997.9.1
• Synthetic Studies on the Fluorinated Analogs for the Putative Oxindole-Type Metabolites of 5-Halotryptamines
  作者：Yoshio Takeuchi、Tomoya Fujiwara、Masaru Miura、Takayuki Seki

  DOI：10.3987/com-08-s(d)70

  日期：——

  The suitably protected precursors for direct fluorination, N(b)-Boc di-protected 5-fluorotryptamine (13), N(b)-acetyl-N(b)-Boc protected 5-halotryptamines (15a-c), were treated with Selectfluor (TM) in MeCN/water in the presence of NaHCO(3) to give the corresponding 3-fluorooxindoles 14 and 16a-c in good yields. Removal of the protecting groups of 14 and 16a-c produced (3,5-difluorooxindol-3-yl)ethylamine (8) and N-acetyl-(3-fluoro-5-halooxindol-3-yl)ethylamines (9a-c) in excellent yields, respectively. These compounds are potentially non-epimerizable analogs for the putative metabolites of 5-fluorotryptamine (6) and N(b)-acetyl-5-halotryptamines (7a-c).