5-amino-7-(ethoxycarbamoyl)-6-(2-hydroxyethyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene hydrochloride | 134288-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-amino-7-(ethoxycarbamoyl)-6-(2-hydroxyethyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene hydrochloride
• CAS: 134288-19-0
• 化学式: C₁₉H₃₀N₂O₃*ClH
• 分子量: 370.92
• InChiKey: RFECEJXGXXBMLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  84.58
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-amino-7-(ethoxycarbamoyl)-6-(2-hydroxyethyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene hydrochloride 在 tris(triphenylphosphine)ruthenium(II) chloride 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以78%的产率得到4-(ethoxycarbamoyl)-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
• 作为产物：
  描述：

  1,1,4,4,6-五甲基-1,2,3,4-四氢化萘 在 palladium on activated charcoal 硫酸 、 硝酸 、 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 、 1,2-二氯乙烷 为溶剂， 反应 30.0h， 生成 5-amino-7-(ethoxycarbamoyl)-6-(2-hydroxyethyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene hydrochloride
  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