(1H-吲哚-3-基)氨基甲酸叔丁酯 | 1199215-71-8

• 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
• 中文名称: (1H-吲哚-3-基)氨基甲酸叔丁酯
• 英文名称: tert-butyl 1H-indol-3-ylcarbamate
• 英文别名: N-Boc 3-aminoindole；tert-butyl N-(1H-indol-3-yl)carbamate
• CAS: 1199215-71-8
• 化学式: C₁₃H₁₆N₂O₂
• mdl: MFCD13248702
• 分子量: 232.282
• InChiKey: YIFUEEQYEIDYGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  350.4±15.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (1H-吲哚-3-基)氨基甲酸叔丁酯 在 盐酸 、 aluminum (III) chloride 、 氯化亚砜 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 13.0h， 生成 (4-methoxynaphthalen-1-yl)(5H-pyrimido[5,4-b]indol-4-yl)methanone
  参考文献：
  名称：

  Total Synthesis of 4-Azaeudistomin Y1 and Analogues by Inverse-Electron­Demand Diels-Alder Reactions of 3-Aminoindoles with 1,3,5-Triazines

  摘要：

  A new inverse-electron-demand Diels-Alder (IDA) reaction of 3-aminoindoles as dienophiles was developed for the efficient preparation of 4-aza-beta-carbolines in high yields. Because N-1-unprotected 3-aminoindoles show poor thermal stability, a one-pot protocol was developed that combines the removal of tert-butoxycarbonyl protecting groups with the IDA reaction. This protocol, using tert-butyl 1H-indol-3-ylcarbamates as reactants, gave the corresponding IDA products in excellent yields. The new IDA methodology was used in a total synthesis of 4-azaeudistomin Y-1, which was obtained in 57% overall yield in four steps. Moreover, the chemistry is suitable for the rapid preparation, through either Friedel-Crafts acylation or amide-formation reactions, of analogues that are useful for exploring structure-activity relationships at the C-1-position.

  DOI：

  10.1055/s-0032-1316857
• 作为产物：
  描述：

  3-吲哚甲酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 53.0h， 生成 (1H-吲哚-3-基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Total Synthesis of 4-Azaeudistomin Y1 and Analogues by Inverse-Electron­Demand Diels-Alder Reactions of 3-Aminoindoles with 1,3,5-Triazines

  摘要：

  A new inverse-electron-demand Diels-Alder (IDA) reaction of 3-aminoindoles as dienophiles was developed for the efficient preparation of 4-aza-beta-carbolines in high yields. Because N-1-unprotected 3-aminoindoles show poor thermal stability, a one-pot protocol was developed that combines the removal of tert-butoxycarbonyl protecting groups with the IDA reaction. This protocol, using tert-butyl 1H-indol-3-ylcarbamates as reactants, gave the corresponding IDA products in excellent yields. The new IDA methodology was used in a total synthesis of 4-azaeudistomin Y-1, which was obtained in 57% overall yield in four steps. Moreover, the chemistry is suitable for the rapid preparation, through either Friedel-Crafts acylation or amide-formation reactions, of analogues that are useful for exploring structure-activity relationships at the C-1-position.

  DOI：

  10.1055/s-0032-1316857

文献信息

• Chiral Phosphoric Acid Catalyzed Highly Enantioselective Friedel–Crafts Alkylation Reaction of C3-Substituted Indoles to β,γ-Unsaturated α-Ketimino Esters
  作者：Bo Bi、Qin-Xin Lou、Yu-Yang Ding、Sheng-Wei Chen、Sha-Sha Zhang、Wen-Hui Hu、Jun-Ling Zhao

  DOI：10.1021/ol5035222

  日期：2015.2.6

  A highly enantioselective C2 Friedel–Crafts alkylation reaction of 3-substituted indoles to β,γ-unsaturated α-ketimino esters has been developed. This reaction was efficiently catalyzed by a chiral phosphoric acid catalyst. The corresponding C2-substituted indole derivatives, bearing an α-ketimino ester motif, were obtained in moderate to high yields (up to 93%) and with high enantioselectivities (up

  已经开发出一种高度对映选择性的3取代的吲哚与β，γ-不饱和α-酮亚胺酸酯的C2 Friedel-Crafts烷基化反应。该反应被手性磷酸催化剂有效地催化。获得具有α-酮亚胺基酸酯基序的相应的C 2-取代的吲哚衍生物，其具有中等至高产率（高达93％）和高对映选择性（高达＞ 99％ee）。
• Three-component reaction involving metal-free heteroannulation of N-Boc-3-amido indole, aryl aldehydes, and aromatic alkynes under microwave conditions: synthesis of highly diversified δ-carbolines
  作者：Sudhir K. Sharma、Anil K. Mandadapu、Mohammad Saifuddin、Sahaj Gupta、Piyush K. Agarwal、Ashok K. Mandwal、Harsh M. Gauniyal、Bijoy Kundu

  DOI：10.1016/j.tetlet.2010.09.054

  日期：2010.11

  An efficient synthesis toward highly diversified delta-carbolines via one-pot multicomponent reaction using N-Boc-3-amido indoles, aryl aldehydes, and aromatic terminal alkynes under microwave conditions has been described. (C) 2010 Elsevier Ltd. All rights reserved.
• CN117049995
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  公开号：——

  公开（公告）日：——