ethyl 2-(3-(2-(tert-butoxycarbonylamino)ethyl)-1H-indol-2-yl)acetate | 1152303-67-7

• 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: ethyl 2-(3-(2-(tert-butoxycarbonylamino)ethyl)-1H-indol-2-yl)acetate
• 英文别名: ethyl 2-[3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1H-indol-2-yl]acetate
• CAS: 1152303-67-7
• 化学式: C₁₉H₂₆N₂O₄
• 分子量: 346.426
• InChiKey: DRKHAKZEYOPGAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-(2-(tert-butoxycarbonylamino)ethyl)-1H-indol-2-yl)acetate 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 sodium tetrahydroborate 、 (2S,5S)-5-((1H-indol-3-yl)methyl)-2-tert-butyl-3-methylimidazolidin-4-one 、 乙醇 、 碳酸氢钠 、 三乙胺 、 三氟乙酸 、 三氯乙酸 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 77.0h， 生成 蕊木宁
  参考文献：
  名称：

  对映选择性Michael / Aza-Michael /环化有机胺到四环螺旋吲哚啉：Kopsinine和Aspidofractine的简明全合成

  摘要：

  AbstractKopsinine and related alkaloids are attractive synthetic targets because of their structural complexity and biological activities. An organocatalytic Michael addition/aza‐Michael addition/cyclization cascade sequence has been developed for the enantioselective preparation of tetracyclic spiroindolines from 2,3‐disubstituted indoles and propargyl aldehyde in moderate to good yields and good to excellent enantioselectivities. The synthetic value of these advanced structures has been demonstrated by the synthesis of kopsinine and related alkaloids. Key steps for the concise synthesis of these alkaloids included an efficient enantioselective construction of tetracyclic spiroindolines bearing a dienamino ester moiety and the organocatalyzed nucleophilic addition of a dienamino ester to acrolein.magnified image

  DOI：

  10.1002/adsc.201400363
• 作为产物：
  描述：

  2-((乙氧基碳硫代)硫代)乙酸乙酯 、 [2-(1H-吲哚-3-基)乙基]氨基甲酸叔丁酯 在 过氧化双月桂酰 作用下， 以 1,2-二氯乙烷 为溶剂， 以53%的产率得到ethyl 2-(3-(2-(tert-butoxycarbonylamino)ethyl)-1H-indol-2-yl)acetate
  参考文献：
  名称：

  氮杂并[4,5-的合成b ]吲哚酮通过的分子间自由基氧化性取代Ñ -Boc色胺†

  摘要：

  使用N- Boc保护的色胺上具有黄药酸酯氧化性芳族取代基的azepino [4,5- b ]吲哚酮衍生物的两步合成方法，使用过氧化二月桂酰 描述了作为引发剂和氧化剂的（DLP）。

  DOI：

  10.1039/b821260k

文献信息

• Synthesis of azepino[4,5-b]indolones via an intermolecular radical oxidative substitution of N-Boc tryptamine
  作者：Paul E. Reyes-Gutiérrez、Rubén O. Torres-Ochoa、Roberto Martínez、Luis D. Miranda

  DOI：10.1039/b821260k

  日期：——

  A two-step protocol for the synthesis of azepino[4,5-b]indolone derivatives featuring a xanthate radical oxidative aromatic substitution on the N-Boc protected tryptamine, using dilauroyl peroxide (DLP) as initiator and oxidant, is described.

  使用N- Boc保护的色胺上具有黄药酸酯氧化性芳族取代基的azepino [4,5- b ]吲哚酮衍生物的两步合成方法，使用过氧化二月桂酰 描述了作为引发剂和氧化剂的（DLP）。
• Enantioselective Intermolecular Formal [3 + 3] Cycloaddition of 2,3-Disubstituted Indoles with Acrolein
  作者：Jianbiao Huang、Long Zhao、Yong Liu、Weiguo Cao、Xiaoyu Wu

  DOI：10.1021/ol401809d

  日期：2013.9.6

  An expedient enantioselective synthesis of highly substituted hydrocarbazoles has been realized by an organocatalyzed formal [3 + 3] cycloaddition between acrolein and 2,3-disubstituted indoles. Tricyclic hydrocarbazoles were obtained from a broad range of 2,3-disubstituted indoles and acrolein in good to excellent yields and excellent enantioselectivites.
• Enantioselective Michael/aza-Michael/Cyclization Organocascade to Tetracyclic Spiroindolines: Concise Total Synthesis of Kopsinine and Aspidofractine
  作者：Xiaoyu Wu、Jianbiao Huang、Beibei Guo、Long Zhao、Yong Liu、Jie Chen、Weiguo Cao

  DOI：10.1002/adsc.201400363

  日期：2014.11.3

  AbstractKopsinine and related alkaloids are attractive synthetic targets because of their structural complexity and biological activities. An organocatalytic Michael addition/aza‐Michael addition/cyclization cascade sequence has been developed for the enantioselective preparation of tetracyclic spiroindolines from 2,3‐disubstituted indoles and propargyl aldehyde in moderate to good yields and good to excellent enantioselectivities. The synthetic value of these advanced structures has been demonstrated by the synthesis of kopsinine and related alkaloids. Key steps for the concise synthesis of these alkaloids included an efficient enantioselective construction of tetracyclic spiroindolines bearing a dienamino ester moiety and the organocatalyzed nucleophilic addition of a dienamino ester to acrolein.magnified image