3-hydroxyphenanthro[4,3-b][1]benzothiophene | 485824-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-hydroxyphenanthro[4,3-b][1]benzothiophene
• 英文别名: 3-Thiapentacyclo[11.8.0.02,10.04,9.016,21]henicosa-1(13),2(10),4,6,8,11,14,16(21),17,19-decaen-18-ol
• CAS: 485824-30-4
• 化学式: C₂₀H₁₂OS
• 分子量: 300.381
• InChiKey: ZHHRYFZHNXGERN-UHFFFAOYSA-N

物化性质

• 沸点：
  582.0±23.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxyphenanthro[4,3-b][1]benzothiophene 在 sodium tetrahydroborate 、 potassium dihydrogenphosphate 、 potassium nitrososulfonate 、 Adogen-464 、 氧气 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 63.0h， 生成 trans-3,4-dihydroxy-3,4-dihydrophenanthro[4,3-b][1]benzothiophene
  参考文献：
  名称：

  Synthesis of Dihydrodiol Metabolites Implicated in the Mechanism of Carcinogenesis of Phenanthro[4,3-b][1]benzothiophene and Phenanthro[3,4-b][1]benzothiophene, the Polycyclic Sulfur Heterocycles with a “Fjord” Structure

  摘要：

  Dihydrodiols, which are potential proximate carcinogens of phenanthro[4,3-b][1]benzothiophene (3) and phenanthro[3,4-b] [1]benzothiophene (4) and possess a "fjord" structure, were synthesized. The dihydrodiols synthesized were trans-3,4-dihydroxy-3,4-dihydrophenanthro[4,3-b] [1]benzothiophene (5) and trans-3,4-dihydroxy-3,4-dihydrophenanthro [3,4-b] [ 11 benzothiophene (6). The precursors to the dihydrodiols 5 and 6 were 3-methoxyphenanthro[4,3-b][1]benzothiophene (11) and 3-methoxyphenanthro[3,4-b][1]benzothiophene (16). Compound 11 was obtained via Suzuki cross-coupling reaction of easily accessible starting materials. However, this synthetic strategy utilizing Suzuki reaction for the preparation of 16 was comparatively less productive than that described previously due to time-consuming synthesis of the starting material(s), and extremely poor yield associated with cyclization of the epoxide 15 to 16. The methoxy derivatives 11 and 16 were converted to the corresponding dihydrodiols 5 and 6 by a sequence involving demethylation, oxidation, and reduction. The trans-stereochemistry of the dihydrodiols was established by H-1 NMR, which indicated a large coupling constant between vicinal carbinol protons. The UV spectra of the dihydrodiols 5 and 6 are presented.

  DOI：

  10.1021/jo020493l
• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲醛 在 氢氧化钾 、 四(三苯基膦)钯 、 甲烷磺酸 、 三溴化硼 、 cesium fluoride 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 67.0h， 生成 3-hydroxyphenanthro[4,3-b][1]benzothiophene
  参考文献：
  名称：

  Synthesis of Dihydrodiol Metabolites Implicated in the Mechanism of Carcinogenesis of Phenanthro[4,3-b][1]benzothiophene and Phenanthro[3,4-b][1]benzothiophene, the Polycyclic Sulfur Heterocycles with a “Fjord” Structure

  摘要：

  Dihydrodiols, which are potential proximate carcinogens of phenanthro[4,3-b][1]benzothiophene (3) and phenanthro[3,4-b] [1]benzothiophene (4) and possess a "fjord" structure, were synthesized. The dihydrodiols synthesized were trans-3,4-dihydroxy-3,4-dihydrophenanthro[4,3-b] [1]benzothiophene (5) and trans-3,4-dihydroxy-3,4-dihydrophenanthro [3,4-b] [ 11 benzothiophene (6). The precursors to the dihydrodiols 5 and 6 were 3-methoxyphenanthro[4,3-b][1]benzothiophene (11) and 3-methoxyphenanthro[3,4-b][1]benzothiophene (16). Compound 11 was obtained via Suzuki cross-coupling reaction of easily accessible starting materials. However, this synthetic strategy utilizing Suzuki reaction for the preparation of 16 was comparatively less productive than that described previously due to time-consuming synthesis of the starting material(s), and extremely poor yield associated with cyclization of the epoxide 15 to 16. The methoxy derivatives 11 and 16 were converted to the corresponding dihydrodiols 5 and 6 by a sequence involving demethylation, oxidation, and reduction. The trans-stereochemistry of the dihydrodiols was established by H-1 NMR, which indicated a large coupling constant between vicinal carbinol protons. The UV spectra of the dihydrodiols 5 and 6 are presented.

  DOI：

  10.1021/jo020493l

文献信息

• Synthesis of Dihydrodiol Metabolites Implicated in the Mechanism of Carcinogenesis of Phenanthro[4,3-<i>b</i>][1]benzothiophene and Phenanthro[3,4-<i>b</i>][1]benzothiophene, the Polycyclic Sulfur Heterocycles with a “Fjord” Structure
  作者：Subodh Kumar

  DOI：10.1021/jo020493l

  日期：2002.12.1

  Dihydrodiols, which are potential proximate carcinogens of phenanthro[4,3-b][1]benzothiophene (3) and phenanthro[3,4-b] [1]benzothiophene (4) and possess a "fjord" structure, were synthesized. The dihydrodiols synthesized were trans-3,4-dihydroxy-3,4-dihydrophenanthro[4,3-b] [1]benzothiophene (5) and trans-3,4-dihydroxy-3,4-dihydrophenanthro [3,4-b] [ 11 benzothiophene (6). The precursors to the dihydrodiols 5 and 6 were 3-methoxyphenanthro[4,3-b][1]benzothiophene (11) and 3-methoxyphenanthro[3,4-b][1]benzothiophene (16). Compound 11 was obtained via Suzuki cross-coupling reaction of easily accessible starting materials. However, this synthetic strategy utilizing Suzuki reaction for the preparation of 16 was comparatively less productive than that described previously due to time-consuming synthesis of the starting material(s), and extremely poor yield associated with cyclization of the epoxide 15 to 16. The methoxy derivatives 11 and 16 were converted to the corresponding dihydrodiols 5 and 6 by a sequence involving demethylation, oxidation, and reduction. The trans-stereochemistry of the dihydrodiols was established by H-1 NMR, which indicated a large coupling constant between vicinal carbinol protons. The UV spectra of the dihydrodiols 5 and 6 are presented.