1,3-dibromo-5,6,7,8-tetrahydronaphthalen-2-ol | 861332-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,3-dibromo-5,6,7,8-tetrahydronaphthalen-2-ol
• 英文别名: 1,3-dibromo-5,6,7,8-tetrahydro-[2]naphthol；5.7-Dibrom-tetralol-(6)；5.7-Dibrom-6-oxy-1.2.3.4-tetrahydro-naphthalin；5.7-Dibrom-6-oxy-tetralin；1,3-Dibrom-5,6,7,8-tetrahydro-[2]naphthol
• CAS: 861332-56-1
• 化学式: C₁₀H₁₀Br₂O
• 分子量: 305.997
• InChiKey: UXHJZXXORPMTLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  苄异腈 、 1,3-dibromo-5,6,7,8-tetrahydronaphthalen-2-ol 在 potassium phosphate 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 以81%的产率得到6-bromo-2,3-diphenyl-7,8,9,10-tetrahydronaphtho[2',3':4,5]furo[2,3-b]pyrazine
  参考文献：
  名称：

  Porous Organic Polymer-Derived Nanopalladium Catalysts for Chemoselective Synthesis of Antitumor Benzofuro[2,3-b]pyrazine from 2-Bromophenol and Isonitriles

  摘要：

  An efficient strategy for the synthesis of benzofuro[2,3-b]pyrazines was developed. These tricyclic scaffolds were formed through a multistep cascade sequence, which includes double insertion of isonitriles and chemoselective bicyclization. In this reaction, a nanopalladium was used as a recyclable catalyst. Product 3w exhibited excellent anticancer activity toward T-24 (IC50 = 12.5 +/- 0.9 mu M) and HeLa (IC50 = 14.7 +/- 1.6 mu M) cells. We also explored the action mechanism of 3w on T-24 cells.

  DOI：

  10.1021/acs.orglett.9b01230
• 作为产物：
  描述：

  5,6,7,8-四氢-2-萘酚 在 四氯化碳 、 溴 作用下， 生成 1,3-dibromo-5,6,7,8-tetrahydronaphthalen-2-ol
  参考文献：
  名称：

  Schroeter, Justus Liebigs Annalen der Chemie, 1922, vol. 426, p. 132

  摘要：

  DOI：

文献信息

• Preparation of <i>o</i>-Fluorophenols from Nonaromatic Precursors: Mechanistic Considerations for Adaptation to Fluorine-18 Radiolabeling
  作者：Norio Yasui、Christopher G. Mayne、John A. Katzenellenbogen

  DOI：10.1021/acs.orglett.5b02640

  日期：2015.11.20

  The preparation of fluorine-18 labeled o-fluorophenols at high specific activity is challenging and requires use of [F-18]fluoride ion as the radioisotope source. As a novel, alternative approach, we found that treatment of alpha-diazocyclohexenones with Selectfluor and Et3N center dot 3HF followed by HF elimination and tautomerization afforded o-fluorophenols regioselectively and rapidly. To adapt this chemistry to F-18 radiolabeling, using bromine electrophiles in place of Selectfluor gave the o-fluorophenol via an alpha-bromo-alpha-fluoroketone intermediate in lower but still reasonable yields.
• Selander,H.; Nilsson,J.L.G., Acta Chemica Scandinavica (1947), 1971, vol. 25, p. 1175 - 1181
  作者：Selander,H.、Nilsson,J.L.G.

  DOI：——

  日期：——
• Jakes, Collection of Czechoslovak Chemical Communications, vol. 1, p. 250
  作者：Jakes

  DOI：——

  日期：——
• Jakes, Collection of Czechoslovak Chemical Communications, vol. 1, p. 250,255
  作者：Jakes

  DOI：——

  日期：——