4-(N-methylamino)-6,7-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylbenzo)indole | 134288-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 4-(N-methylamino)-6,7-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylbenzo)indole
• 英文别名: N,6,6,9,9-pentamethyl-7,8-dihydro-1H-benzo[g]indol-4-amine
• CAS: 134288-20-3
• 化学式: C₁₇H₂₄N₂
• 分子量: 256.391
• InChiKey: ADEMYOMXKSPDJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(N-methylamino)-6,7-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylbenzo)indole 在 2,6-二甲基吡啶 、 sodium carbonate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 ethyl (S)-3-(4-(methyl(1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-6,7-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylbenzo)-1H-indol-3-yl)-2-oximidopropionate
  参考文献：
  名称：

  Synthesis of a tetramethyl analog of teleocidin

  摘要：

  A simplified tetramethyl analogue 3 of Teleocidin B-4 (1) has been synthesized from dinitrotoluene 6 via indole 4. The valine moiety of analogue 3 was provided by the coupling of (N-methylamino)indole 16 derived from 4 with the triflate of (R)-2-hydroxyvaleric acid benzyl ester, and the tryptophanyl portion was constructed by alkylation of the resulting (S)-N-valylindole 17 with ethyl (3-bromo-2-oximido)propionate to give the oxime 18. After reduction to the diastereomeric amines 20 and 21, closure to the 9-membered lactam-esters 24 and 23 (respectively) was accomplished using BOP. Separation and reduction of the esters led to teleocidin analogue 3 and its epimeric alcohol 25, respectively.

  DOI：

  10.1021/jo00015a026
• 作为产物：
  描述：

  1,2,3,4-tetrahydro-1,1,4,4,6-pentamethyl-5,7-dinitronaphthalene 在 palladium on activated charcoal lithium aluminium tetrahydride 、 tris(triphenylphosphine)ruthenium(II) chloride 、 苄基三甲基氢氧化铵 、 铁粉 、 碳酸氢钠 、 溶剂黄146 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 31.5h， 生成 4-(N-methylamino)-6,7-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylbenzo)indole
  参考文献：
  名称：

  Synthesis of a tetramethyl analog of teleocidin

  摘要：

  A simplified tetramethyl analogue 3 of Teleocidin B-4 (1) has been synthesized from dinitrotoluene 6 via indole 4. The valine moiety of analogue 3 was provided by the coupling of (N-methylamino)indole 16 derived from 4 with the triflate of (R)-2-hydroxyvaleric acid benzyl ester, and the tryptophanyl portion was constructed by alkylation of the resulting (S)-N-valylindole 17 with ethyl (3-bromo-2-oximido)propionate to give the oxime 18. After reduction to the diastereomeric amines 20 and 21, closure to the 9-membered lactam-esters 24 and 23 (respectively) was accomplished using BOP. Separation and reduction of the esters led to teleocidin analogue 3 and its epimeric alcohol 25, respectively.

  DOI：

  10.1021/jo00015a026

文献信息

• WEBB, ROBERT R. (II);VENUTI, MICHAEL C.;EIGENBROT, CHARLES, J. ORG. CHEM., 56,(1991) N5, C. 4706-4713
  作者：WEBB, ROBERT R. (II)、VENUTI, MICHAEL C.、EIGENBROT, CHARLES

  DOI：——

  日期：——
• Synthesis of a tetramethyl analog of teleocidin
  作者：Robert R. Webb、Michael C. Venuti、Charles Eigenbrot

  DOI：10.1021/jo00015a026

  日期：1991.7

  A simplified tetramethyl analogue 3 of Teleocidin B-4 (1) has been synthesized from dinitrotoluene 6 via indole 4. The valine moiety of analogue 3 was provided by the coupling of (N-methylamino)indole 16 derived from 4 with the triflate of (R)-2-hydroxyvaleric acid benzyl ester, and the tryptophanyl portion was constructed by alkylation of the resulting (S)-N-valylindole 17 with ethyl (3-bromo-2-oximido)propionate to give the oxime 18. After reduction to the diastereomeric amines 20 and 21, closure to the 9-membered lactam-esters 24 and 23 (respectively) was accomplished using BOP. Separation and reduction of the esters led to teleocidin analogue 3 and its epimeric alcohol 25, respectively.