5'-methoxy-8'-(8-methoxynaphthalen-1-yl)oxyspiro[1,3-dioxolane-2,4'-2,3-dihydro-1H-naphthalene] | 208346-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-methoxy-8'-(8-methoxynaphthalen-1-yl)oxyspiro[1,3-dioxolane-2,4'-2,3-dihydro-1H-naphthalene]
• CAS: 208346-34-3
• 化学式: C₂₄H₂₄O₅
• 分子量: 392.452
• InChiKey: PEXYSOBCBPMCJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5'-methoxy-8'-(8-methoxynaphthalen-1-yl)oxyspiro[1,3-dioxolane-2,4'-2,3-dihydro-1H-naphthalene] 在 sodium acetate 、 4-甲基苯磺酸吡啶 、 三溴化硼 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 水 、 丙酮 、 苯 为溶剂， 反应 85.0h， 生成
  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-3,4-dihydro-2H-naphthalen-1-one 在 copper(I) oxide 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 吡啶 、 苯 为溶剂， 反应 54.0h， 生成 5'-methoxy-8'-(8-methoxynaphthalen-1-yl)oxyspiro[1,3-dioxolane-2,4'-2,3-dihydro-1H-naphthalene]
  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

• Total Synthesis of Palmarumycin CP₁ and (±)-Deoxypreussomerin A
  作者：Peter Wipf、Jae-Kyu Jung

  DOI：10.1021/jo980576v

  日期：1998.5.1
• 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.