2-<1-(6-Methoxynaphthyl)>ethyl Methanesulfonate | 145627-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-<1-(6-Methoxynaphthyl)>ethyl Methanesulfonate
• 英文别名: 2-(6-Methoxynaphthalen-1-yl)ethyl methanesulfonate
• CAS: 145627-74-3
• 化学式: C₁₄H₁₆O₄S
• 分子量: 280.345
• InChiKey: GRDVXIHBOIUGGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-<1-(6-Methoxynaphthyl)>ethyl Methanesulfonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以99%的产率得到2-<1-(6-Methoxynaphthyl)>ethyl Iodide
  参考文献：
  名称：

  Synthesis of the active dihydrodiol and diol epoxide metabolites of the steroid-related carcinogen 15,16-dihydrocyclopenta[a]phenanthrene and its 11-methyl derivative

  摘要：

  Cyclopenta[a]phenanthrenes are a class of environmentally occurring carcinogens that are structurally related to sterols. While the parent hydrocarbon is biologically inactive, its 11-methyl and 17-keto derivatives are relatively potent carcinogens. Recent research has identified trans-3,4-dihydrodiol metabolites as the metabolic precursors of the corresponding anti- and/or syn-diol epoxides, implicated as the ultimate carcinogenic forms that bind to DNA. We now report the synthesis of the trans-3,4-dihydrodiol derivatives of cyclcopenta[a]phenanthrene and 11-methylcyclopenta[a]phenanthrene, 3a and 3b, respectively, and the corresponding anti- and syn-diol epoxides of each of these hydrocarbons, 4a, 4b and 5a, 5b, respectively. Syntheses of the analogous trans-3,4-dihydrodiol metabolites of the 17-keto derivatives of cyclopenta[a]phenanthrene and 11-methylcyclopenta[a]phenanthrene are described in the accompanying paper.

  DOI：

  10.1021/jo00054a017
• 作为产物：
  描述：

  2-<1-(6-methoxynaphthyl)>ethanol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到2-<1-(6-Methoxynaphthyl)>ethyl Methanesulfonate
  参考文献：
  名称：

  Synthesis of the active dihydrodiol and diol epoxide metabolites of the steroid-related carcinogen 15,16-dihydrocyclopenta[a]phenanthrene and its 11-methyl derivative

  摘要：

  Cyclopenta[a]phenanthrenes are a class of environmentally occurring carcinogens that are structurally related to sterols. While the parent hydrocarbon is biologically inactive, its 11-methyl and 17-keto derivatives are relatively potent carcinogens. Recent research has identified trans-3,4-dihydrodiol metabolites as the metabolic precursors of the corresponding anti- and/or syn-diol epoxides, implicated as the ultimate carcinogenic forms that bind to DNA. We now report the synthesis of the trans-3,4-dihydrodiol derivatives of cyclcopenta[a]phenanthrene and 11-methylcyclopenta[a]phenanthrene, 3a and 3b, respectively, and the corresponding anti- and syn-diol epoxides of each of these hydrocarbons, 4a, 4b and 5a, 5b, respectively. Syntheses of the analogous trans-3,4-dihydrodiol metabolites of the 17-keto derivatives of cyclopenta[a]phenanthrene and 11-methylcyclopenta[a]phenanthrene are described in the accompanying paper.

  DOI：

  10.1021/jo00054a017

文献信息

• Synthesis of the active dihydrodiol and diol epoxide metabolites of the steroid-related carcinogen 15,16-dihydrocyclopenta[a]phenanthrene and its 11-methyl derivative
  作者：Robert J. Young、Cecilia Cortez、Ernestina Luna、Hongmee Lee、Ronald G. Harvey

  DOI：10.1021/jo00054a017

  日期：1993.1

  Cyclopenta[a]phenanthrenes are a class of environmentally occurring carcinogens that are structurally related to sterols. While the parent hydrocarbon is biologically inactive, its 11-methyl and 17-keto derivatives are relatively potent carcinogens. Recent research has identified trans-3,4-dihydrodiol metabolites as the metabolic precursors of the corresponding anti- and/or syn-diol epoxides, implicated as the ultimate carcinogenic forms that bind to DNA. We now report the synthesis of the trans-3,4-dihydrodiol derivatives of cyclcopenta[a]phenanthrene and 11-methylcyclopenta[a]phenanthrene, 3a and 3b, respectively, and the corresponding anti- and syn-diol epoxides of each of these hydrocarbons, 4a, 4b and 5a, 5b, respectively. Syntheses of the analogous trans-3,4-dihydrodiol metabolites of the 17-keto derivatives of cyclopenta[a]phenanthrene and 11-methylcyclopenta[a]phenanthrene are described in the accompanying paper.