tert-butyl (2-((5-methoxy-1H-indol-3-yl)methyl)phenyl)carbamate | 890408-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (2-((5-methoxy-1H-indol-3-yl)methyl)phenyl)carbamate
• 英文别名: tert-butyl N-[2-[(5-methoxy-1H-indol-3-yl)methyl]phenyl]carbamate
• CAS: 890408-53-4
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: TVICMINITCCLKP-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：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-methylbut-3-en-2-yl carbonate 、 tert-butyl (2-((5-methoxy-1H-indol-3-yl)methyl)phenyl)carbamate 在 三乙基硼 、 potassium tert-butylate 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 (±)-9-(dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl)-9H-carbazole 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 5.67h， 以88%的产率得到(±)-(5aR,10bS)-tert-butyl 9-methoxy-10b-(2-methylbut-3-en-2-yl)-5a,6,10b,11-tetrahydro-5H-indolo[2,3-b]quinoline-5-carboxylate
  参考文献：
  名称：

  Ir-Catalyzed Reverse Prenylation of 3-Substituted Indoles: Total Synthesis of (+)-Aszonalenin and (−)-Brevicompanine B

  摘要：

  The selective reverse prenylation of 3-substituted-1H-indoles at C3 is described. The iridium-catalyzed reaction proceeds with high branched to linear selectivity (>20:1) for a variety of indoles. In addition, a diastereoselective reverse prenylation of tryptophan methyl ester is disclosed, and its synthetic utility is demonstrated in the synthesis of (+)-aszonalenin and (-)-brevicompanine B.

  DOI：

  10.1021/ja509893s
• 作为产物：
  描述：

  邻氨基苯甲醇 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 生成 tert-butyl (2-((5-methoxy-1H-indol-3-yl)methyl)phenyl)carbamate
  参考文献：
  名称：

  Palladium-Catalyzed Enantioselective C-3 Allylation of 3-Substituted-1H-Indoles Using Trialkylboranes

  摘要：

  We have developed a new enantioselective C-3 allylation of 3-substituted indoles using allyl alcohol and trialkylboranes. Asymmetric syntheses of 3,3-disubstituted indolines and indolenines in enantiomeric excesses up to 90% have been achieved using the bulky borane 9-BBN-C6H13 as the promoter of the reaction. The dependence of the selectivity on the nature of the borane suggests that the boron reagent has a role beyond promoting ionization of the allyl alcohol. A protocol for oxidation of indolenines to oxindoles has also been developed and led to a formal synthesis of (-)-phenserine.

  DOI：

  10.1021/ja0608139