5-(8-Hydroxy-naphthalen-1-yloxy)-1,2,3,4-tetrahydro-naphthalene-1,8-diol | 328005-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(8-Hydroxy-naphthalen-1-yloxy)-1,2,3,4-tetrahydro-naphthalene-1,8-diol
• 英文别名: 5-(8-Hydroxynaphthalen-1-yl)oxy-1,2,3,4-tetrahydronaphthalene-1,8-diol
• CAS: 328005-58-9
• 化学式: C₂₀H₁₈O₄
• 分子量: 322.361
• InChiKey: QTGIHUYFIPNSNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(8-Hydroxy-naphthalen-1-yloxy)-1,2,3,4-tetrahydro-naphthalene-1,8-diol 在 碘苯二乙酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 0.5h， 以87%的产率得到(+/-)-8-hydroxy-1-oxo-1,4,5,6,7,8-hexahydronaphthalene-4-spiro-2'-naphthol[1'',8''-de][1',3']dioxin
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxypreussomerin A and palmarumycin CP1 and related naphthoquinone spiroketals

  摘要：

  Oxidative cyclization of bis-hydroxynaphthyl ethers allows concise total syntheses of palmarumycin CP1 and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1-tetralone (8). Polymer-bound triphenyl phosphine was found to be a superior reagent for the rapid preparation of a small library of palmarumycin analogs. Preliminary biological evaluation of naphthoquinone spiroketals against MCF-7 and MDA-MB-231 human breast cancer cells revealed several low-micromolar growth inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00936-4
• 作为产物：
  描述：

  5-hydroxy-8-methoxy-1,2,3,4-tetrahydronaphthalene-1-spiro-2'-dioxolane 在 copper(I) oxide 、 lithium aluminium tetrahydride 、 三溴化硼 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 吡啶 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 47.0h， 生成 5-(8-Hydroxy-naphthalen-1-yloxy)-1,2,3,4-tetrahydro-naphthalene-1,8-diol
  参考文献：
  名称：

  Synthesis and biological evaluation of deoxypreussomerin A and palmarumycin CP1 and related naphthoquinone spiroketals

  摘要：

  Oxidative cyclization of bis-hydroxynaphthyl ethers allows concise total syntheses of palmarumycin CP1 and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1-tetralone (8). Polymer-bound triphenyl phosphine was found to be a superior reagent for the rapid preparation of a small library of palmarumycin analogs. Preliminary biological evaluation of naphthoquinone spiroketals against MCF-7 and MDA-MB-231 human breast cancer cells revealed several low-micromolar growth inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00936-4

文献信息

• Synthesis and biological evaluation of deoxypreussomerin A and palmarumycin CP1 and related naphthoquinone spiroketals
  作者：Peter Wipf、Jae-Kyu Jung、Sonia Rodrı́guez、John S Lazo

  DOI：10.1016/s0040-4020(00)00936-4

  日期：2001.1

  Oxidative cyclization of bis-hydroxynaphthyl ethers allows concise total syntheses of palmarumycin CP1 and deoxypreussomerin A in 8-9 steps and 15-35% overall yield from 5-hydroxy-8-methoxy-1-tetralone (8). Polymer-bound triphenyl phosphine was found to be a superior reagent for the rapid preparation of a small library of palmarumycin analogs. Preliminary biological evaluation of naphthoquinone spiroketals against MCF-7 and MDA-MB-231 human breast cancer cells revealed several low-micromolar growth inhibitors. (C) 2000 Elsevier Science Ltd. All rights reserved.