6-Methoxyphenanthrene-9-carboxylic acid | 22519-10-4

• 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: 6-Methoxyphenanthrene-9-carboxylic acid
• 英文别名: 6-Methoxy-phenanthren-9-carbonsaeure；3-Methoxy-phenanthren-10-carbonsaeure；3-Methoxy-phenanthren-carbonsaeure-(10)
• CAS: 22519-10-4
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: IREAUGZXYMJCNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Methoxyphenanthrene-9-carboxylic acid 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 、 三氟化硼乙醚 作用下， 生成 9-Chloromethyl-6-methoxyphenanthren
  参考文献：
  名称：

  Shah,D.O.; Trivedi,K.N., Indian Journal of Chemistry, 1975, vol. 13, p. 1272 - 1274

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-3-(2-Aminophenyl)-2-(4-methoxyphenyl)-2-propenoic acid 在 盐酸 、 亚硝酸正戊酯 、 乙醇 作用下， 生成 6-Methoxyphenanthrene-9-carboxylic acid
  参考文献：
  名称：

  Studies in the Phenanthrene Series. VII. 3-Hydroxyacetylphenanthrenes and Amino Ketones and Alcohols Derived from Them. Hydroxyaminophenanthrenes¹

  摘要：

  DOI：

  10.1021/ja01323a028

文献信息

• Synthesis of analogues of cryptopleurine
  作者：S. Foldeak

  DOI：10.1016/s0040-4020(01)97758-0

  日期：1971.1

  New analogues of cryptopleurine with different aromatic methoxyl and chloro substituents have been synthesized. Intermediate isomeric 1-hydroxyphenanthro[9.10b]quinolizidines have been isolated and characterized. Yields in the Pschorr reaction have been improved by the novel use of sulphite ion. Some of the compounds have been found to have antifungal activity.

  已经合成了具有不同的芳族甲氧基和氯取代基的隐叶嘌呤的新类似物。中间异构体1-羟基菲[9.10 b ]喹啉z已被分离和表征。通过新使用亚硫酸根离子可以提高Pschorr反应的收率。已经发现一些化合物具有抗真菌活性。
• Kessar, S. V.; Nadir, U. K.; Gupta, Y. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 1, p. 1 - 3
  作者：Kessar, S. V.、Nadir, U. K.、Gupta, Y. P.、Pahwa, P. S.、Singh, Paramjit

  DOI：——

  日期：——
• Pschorr; Wolfes; Buckow, Chemische Berichte, 1900, vol. 33, p. 165
  作者：Pschorr、Wolfes、Buckow

  DOI：——

  日期：——
• Soluble Catalysts for Improved Pschorr Cyclizations
  作者：Frederick W. Wassmundt、William F. Kiesman

  DOI：10.1021/jo00106a034

  日期：1995.1

  Several improved catalysts for the Pschorr phenanthrene synthesis have been discovered; all are soluble substances which initiate free-radical reactions by electron donation and thereby shorten the reaction time and increase the yield. One technique with K4Fe(CN)(6) in water produced phenanthrene-9-carboxylic acid (6a) in 87% yield, but its application did not extend to substituted examples where the diazonium salt is less soluble in water. A more general procedure with ferrocene in acetone produced not only 6a but also substituted examples 6b-f in yields of 88-94%. A modification which avoids the isolation of diazonium salts was developed for occasional synthetic use.
• KESSAR, S. V.;NADIR, U. K.;GUPTA, Y. P.;PAHWA, P. S.;SINGH, PARAMJIT, INDIAN J. CHEM., 1981, 20, N 1, 1-3
  作者：KESSAR, S. V.、NADIR, U. K.、GUPTA, Y. P.、PAHWA, P. S.、SINGH, PARAMJIT

  DOI：——

  日期：——