ethyl 5-<1'-(tert-butoxycarbonyl)indol-3'-yl>pentanoate | 141972-24-9

• 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 5-<1'-(tert-butoxycarbonyl)indol-3'-yl>pentanoate
• 英文别名: 3-(4-ethoxycarbonyl-butyl)-indole-1-carboxylic acid tert-butyl ester；tert-butyl 3-(5-ethoxy-5-oxopentyl)indole-1-carboxylate
• CAS: 141972-24-9
• 化学式: C₂₀H₂₇NO₄
• 分子量: 345.439
• InChiKey: IROQWIKKLMIZEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-<1'-(tert-butoxycarbonyl)indol-3'-yl>pentanoate 在 四氯化碳 、 lithium cyclohexylisopropylamide 作用下， 生成 ethyl 5-<1'-(tert-butoxycarbonyl)indol-3'-yl>-2-chloropentanoate
  参考文献：
  名称：

  Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 2. Photocyclisation of halogenoacetyl tryptophol derivatives and α-chloro indol-3-ylalkanoate esters

  摘要：

  Irradiation of the trichloroacetates 2, 4 and 5, derived from the corresponding tryptophols, in methanolic acetonitrile results in photocyclisation to the indole 4-position, and the formation of the pyrrolobenzoxocines 9-11. Attempted photocyclisation of the 'reversed' alpha-chloro esters 15a, 15b and 18 was thwarted by readily occurring elimination of HCl, although the dimethyl compound 15c did cyclise to give the cycloheptaindole 20 upon irradiation in acetonitrile.

  DOI：

  10.1039/p19920000813
• 作为产物：
  描述：

  5-(1H-indol-3-yl)pentanoic acid 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 ethyl 5-<1'-(tert-butoxycarbonyl)indol-3'-yl>pentanoate
  参考文献：
  名称：

  Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 2. Photocyclisation of halogenoacetyl tryptophol derivatives and α-chloro indol-3-ylalkanoate esters

  摘要：

  Irradiation of the trichloroacetates 2, 4 and 5, derived from the corresponding tryptophols, in methanolic acetonitrile results in photocyclisation to the indole 4-position, and the formation of the pyrrolobenzoxocines 9-11. Attempted photocyclisation of the 'reversed' alpha-chloro esters 15a, 15b and 18 was thwarted by readily occurring elimination of HCl, although the dimethyl compound 15c did cyclise to give the cycloheptaindole 20 upon irradiation in acetonitrile.

  DOI：

  10.1039/p19920000813

文献信息

• Enantioselective α-Arylation of Aldehydes via Organo-SOMO Catalysis. An Ortho-Selective Arylation Reaction Based on an Open-Shell Pathway
  作者：Jay C. Conrad、Jongrock Kong、Brian N. Laforteza、David W. C. MacMillan

  DOI：10.1021/ja9026902

  日期：2009.8.26

  The intramolecular alpha-arylation of aldehydes has been accomplished using singly occupied molecular orbital (SOMO) catalysis. Selective oxidation of chiral enamines (formed by the condensation of an aldehyde and a secondary amine catalyst) leads to the formation of a 3pi-electron radical species. These chiral SOMO-activated radical cations undergo enantioselective reaction with an array of pendent

  醛的分子内α-芳基化已使用单占分子轨道（SOMO）催化完成。手性烯胺（由醛和仲胺催化剂缩合形成）的选择性氧化导致形成 3pi 电子自由基物种。这些手性 SOMO 活化的自由基阳离子与一系列悬垂的富电子芳烃和杂环进行对映选择性反应，从而有效地提供环状 α-芳基醛产物（10 个例子：> 或 = 70% 产率和 > 或 = 90% ee）。根据我们的自由基机制，当在苯甲醚底物的邻位或对位芳基化之间进行选择时，我们发现芳基化选择性地在邻位进行。