8-hydroxy-5-(8'-hydroxynaphthalen-1'-yloxy)-1,2,3,4-tetrahydronaphthalene-1-spiro-2''-dioxolane | 328005-53-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-hydroxy-5-(8'-hydroxynaphthalen-1'-yloxy)-1,2,3,4-tetrahydronaphthalene-1-spiro-2''-dioxolane
• 英文别名: 4'-(8-hydroxynaphthalen-1-yl)oxyspiro[1,3-dioxolane-2,8'-6,7-dihydro-5H-naphthalene]-1'-ol
• CAS: 328005-53-4
• 化学式: C₂₂H₂₀O₅
• 分子量: 364.398
• InChiKey: FDAVMENFFGKZFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-hydroxy-5-(8'-hydroxynaphthalen-1'-yloxy)-1,2,3,4-tetrahydronaphthalene-1-spiro-2''-dioxolane 在 碘苯二乙酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 2.0h， 以75%的产率得到1-oxo-1,4,5,6,7,8-hexahydronaphthalene-4-spiro-2'-naphthoy[1'',8''-de][1',3']dioxin-8-spiro-2'''-dioxolane
  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：

  在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以96%的产率得到8-hydroxy-5-(8'-hydroxynaphthalen-1'-yloxy)-1,2,3,4-tetrahydronaphthalene-1-spiro-2''-dioxolane
  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.