3-(2-(methylamino)ethyl)-3-reverse-prenyl-N-prenyl oxindole | 1280171-18-7

• 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: 3-(2-(methylamino)ethyl)-3-reverse-prenyl-N-prenyl oxindole
• 英文别名: 3-[2-(Methylamino)ethyl]-3-(2-methylbut-3-en-2-yl)-1-(3-methylbut-2-enyl)indol-2-one；3-[2-(methylamino)ethyl]-3-(2-methylbut-3-en-2-yl)-1-(3-methylbut-2-enyl)indol-2-one
• CAS: 1280171-18-7
• 化学式: C₂₁H₃₀N₂O
• 分子量: 326.482
• InChiKey: NELMFVMHQPQCQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-(methylamino)ethyl)-3-reverse-prenyl-N-prenyl oxindole 在 alane N,N-dimethylethylamine complex 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以54%的产率得到(+/-)-1-methyl-3a-(2-methylbut-3-en-2-yl)-8-(3-methylbut-2-enyl)-1,2,3,3a-tetrahydropyrrolo[2,3-b]indole
  参考文献：
  名称：

  Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy

  摘要：

  A concise and practical strategy to obtain C3 reverse-prenylated pyrrolidinoindoline scaffold has been executed in 28.8% overall yield. The key conjugative step involved a Booker-Milburn-Feudoloff reaction involving an NCS-mediated activation of indole, followed by coupling to C(5) dimethylallylalcohol. This linchpin step proceeded in 74% yield. The overall sequence proceeded in five steps from commercially available N-methyltryptamine with a single protection-deprotection operation and a single redox manipulation. Mechanistic insights of NCS activation, and an ensuing rearrangement of the isoprene unit were gained by rationally varying the C3 substituent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.020
• 作为产物：
  描述：

  ethyl 2-(1H-indole-3-yl)ethylcarbamate 在 1,4-二甲基哌嗪 、 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 sodium hydride 、 caesium carbonate 、 苯硫酚 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 7.75h， 生成 3-(2-(methylamino)ethyl)-3-reverse-prenyl-N-prenyl oxindole
  参考文献：
  名称：

  Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy

  摘要：

  A concise and practical strategy to obtain C3 reverse-prenylated pyrrolidinoindoline scaffold has been executed in 28.8% overall yield. The key conjugative step involved a Booker-Milburn-Feudoloff reaction involving an NCS-mediated activation of indole, followed by coupling to C(5) dimethylallylalcohol. This linchpin step proceeded in 74% yield. The overall sequence proceeded in five steps from commercially available N-methyltryptamine with a single protection-deprotection operation and a single redox manipulation. Mechanistic insights of NCS activation, and an ensuing rearrangement of the isoprene unit were gained by rationally varying the C3 substituent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.020

文献信息

• Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy
  作者：Vasily A. Ignatenko、Ping Zhang、Rajesh Viswanathan

  DOI：10.1016/j.tetlet.2011.01.020

  日期：2011.3

  A concise and practical strategy to obtain C3 reverse-prenylated pyrrolidinoindoline scaffold has been executed in 28.8% overall yield. The key conjugative step involved a Booker-Milburn-Feudoloff reaction involving an NCS-mediated activation of indole, followed by coupling to C(5) dimethylallylalcohol. This linchpin step proceeded in 74% yield. The overall sequence proceeded in five steps from commercially available N-methyltryptamine with a single protection-deprotection operation and a single redox manipulation. Mechanistic insights of NCS activation, and an ensuing rearrangement of the isoprene unit were gained by rationally varying the C3 substituent. (C) 2011 Elsevier Ltd. All rights reserved.