spiro[2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-3,5'-3,4-dihydro-2H-naphthalene]-1',8'-dione | 328005-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: spiro[2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-3,5'-3,4-dihydro-2H-naphthalene]-1',8'-dione
• CAS: 328005-52-3
• 化学式: C₂₀H₁₄O₄
• 分子量: 318.329
• InChiKey: MULJGIPMHSPAJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  spiro[2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-3,5'-3,4-dihydro-2H-naphthalene]-1',8'-dione 在 manganese(IV) oxide 、 4-diphenylphosphinopolystyrene 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 8-(furan-3-ylmethoxy)-1-oxo-1,4-dihydronaphthalene-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：

  (+/-)-8-hydroxy-1-oxo-1,4,5,6,7,8-hexahydronaphthalene-4-spiro-2'-naphthol[1'',8''-de][1',3']dioxin 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以32 mg的产率得到spiro[2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5,7,9(13),10-pentaene-3,5'-3,4-dihydro-2H-naphthalene]-1',8'-dione
  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.