1,2,3,4-tetrahydro-6-(2-hydroxyethyl)-1,1,4,4-tetramethyl-5,7-dinitronaphthalene | 134288-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,3,4-tetrahydro-6-(2-hydroxyethyl)-1,1,4,4-tetramethyl-5,7-dinitronaphthalene
• 英文别名: 2-(5,5,8,8-Tetramethyl-1,3-dinitro-6,7-dihydronaphthalen-2-yl)ethanol
• CAS: 134288-15-6
• 化学式: C₁₆H₂₂N₂O₅
• 分子量: 322.361
• InChiKey: LPFFQDGKFOZYRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-6-(2-hydroxyethyl)-1,1,4,4-tetramethyl-5,7-dinitronaphthalene 在 palladium on activated charcoal 2,6-二甲基吡啶 、 lithium aluminium tetrahydride 、 锂硼氢 、 tris(triphenylphosphine)ruthenium(II) chloride 、 铁粉 、 碳酸氢钠 、 sodium carbonate 、 溶剂黄146 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 46.5h， 生成 (S,R)-1,3,4,5,7,8,10,11,12,13-decahydro-4-(hydroxymethyl)-8,10,10,13,13-pentamethyl-7-(1-methylethyl)-6H-benzo<1,4>diazonino<7,6,5-cd>indol-6-one
  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：

  1,1,4,4,6-五甲基-1,2,3,4-四氢化萘 在 硫酸 、 硝酸 、 苄基三甲基氢氧化铵 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 1,2,3,4-tetrahydro-6-(2-hydroxyethyl)-1,1,4,4-tetramethyl-5,7-dinitronaphthalene
  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.