2-甲氧基-6-(1'-羟基戊基)苯酚 | 92759-34-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-甲氧基-6-(1'-羟基戊基)苯酚
• 英文名称: 2-Methoxy-6-(1'-hydroxypentyl)phenol
• 英文别名: 2-Methoxy-5-(1-hydroxypentyl)phenol；2-(1-Hydroxypentyl)-6-methoxyphenol
• CAS: 92759-34-7
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: DNBQSKNMTLHTFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲氧基-6-(1'-羟基戊基)苯酚 在 5percent Pd/C potassium nitrososulfonate 、 氢气 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 生成 异兰,异索兰
  参考文献：
  名称：

  Isolation, Synthesis, and Structure−Activity Relationships of Bioactive Benzoquinones from Miconia lepidota from the Suriname Rainforest

  摘要：

  Bioactivity-directed fractionation of an EtOAc extract from the leaves of Miconia lepidota afforded the two benzoquinones 2-methoxy-6-heptyl-1,4-benzoquinone (1) and 2-methoxy-6-pentyl-1,4-benzoquinone (primin) (2). This is the first reported isolation of 1. Both quinones 1 and 2 exhibited activity toward mutant yeast strains based on Saccharomyces cerevisiae, indicative of their cytotoxicity and potential anticancer activity. A number of previously synthesized and new analogues were prepared and tested in the same strains. Compounds 1, 2, 2-methoxy-6-butyl-1,4-benzoquinone (5), and 2-methoxy-6-decyl-1,4-benzoquinone (6) were tested in two cytotoxicity assays. In the M109 tumor cell lines, quinones 1, 2, and 6 had an IC50 value of 10 mug/mL. In the A2780 cell line, compounds 1, 2 and 5 had IC50 values of 7.9, 2.9, and 3.2 mug/mL, respectively.

  DOI：

  10.1021/np000219r
• 作为产物：
  描述：

  1-(3-methoxyphenyl)pentan-1-ol 生成 2-甲氧基-6-(1'-羟基戊基)苯酚
  参考文献：
  名称：

  One-Pot Ortho Hydroxylations of 2-(1-Hydroxyalkyl)naphthalenes and (1-Hydroxyalkyl)benzenes

  摘要：

  2-(1- 羟基烷基)-1,4,5,8(或 1,4,5,6,8)-四(或五)甲氧基萘和 2-(1-羟基烷基)-1,4-二甲氧基苯的 3-位羟基化是通过一锅程序完成的。同样的步骤也适用于没有甲氧基取代基的 2-(1-羟基烷基)萘和(1-羟基烷基)苯。

  DOI：

  10.1246/bcsj.61.1221

文献信息

• Ortho Lithiation of 2-Hydroxymethyl-1,4,5,6,8-pentamethoxynaphthalene, a Supplement
  作者：Yasuhiro Tanoue、Akira Terada

  DOI：10.1246/bcsj.64.2295

  日期：1991.7

  The structures of the products in our previous report “One-Pot Ortho Hydroxylations of 2-(1-Hydroxyalkyl)-naphthalenes and (1-Hydroxyalkyl)benzenes” were reexamined by 13CNMR spectra and part of our previous interpretation will be corrected here. The lithiations of 2-(1-hydroxyalkyl)-1,4,5,6,8-pentamethoxynaphthalenes occurred at the 7-position, and not at the 3-position as we reported.

  我们之前的报告“2-(1-羟基烷基)-萘和 (1-羟基烷基)苯的一锅邻羟基化”中的产物结构通过 13CNMR 光谱进行了重新检查，我们之前的部分解释将在此处更正。2-(1-羟烷基)-1,4,5,6,8-五甲氧基萘的锂化发生在 7 位，而不是我们报道的 3 位。
• Koenig, Wilfried A.; Faasch, Holger; Heitsch, Holger, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1993, vol. 48, # 3, p. 387 - 393
  作者：Koenig, Wilfried A.、Faasch, Holger、Heitsch, Holger、Colberg, Cornelia、Hausen, Bjoern M.

  DOI：——

  日期：——
• Arogba, Sunday S., Organic Preparations and Procedures International, 1991, vol. 23, # 5, p. 639 - 644
  作者：Arogba, Sunday S.

  DOI：——

  日期：——
• TANOUE, YASUHIRO;TERADA, AKIRA;SETO, IWAO;UMEZU, YASUO;TSUGE, OTOHIKO, BULL. CHEM. SOC. JAP., 61,(1988) N 4, 1221-1224
  作者：TANOUE, YASUHIRO、TERADA, AKIRA、SETO, IWAO、UMEZU, YASUO、TSUGE, OTOHIKO

  DOI：——

  日期：——
• Isolation, Synthesis, and Structure−Activity Relationships of Bioactive Benzoquinones from <i>Miconia lepidota</i> from the Suriname Rainforest
  作者：A. A. Leslie Gunatilaka、John M. Berger、Randy Evans、James S. Miller、Jan H. Wisse、Kim M. Neddermann、Isia Bursuker、David G. I. Kingston

  DOI：10.1021/np000219r

  日期：2001.1.1

  Bioactivity-directed fractionation of an EtOAc extract from the leaves of Miconia lepidota afforded the two benzoquinones 2-methoxy-6-heptyl-1,4-benzoquinone (1) and 2-methoxy-6-pentyl-1,4-benzoquinone (primin) (2). This is the first reported isolation of 1. Both quinones 1 and 2 exhibited activity toward mutant yeast strains based on Saccharomyces cerevisiae, indicative of their cytotoxicity and potential anticancer activity. A number of previously synthesized and new analogues were prepared and tested in the same strains. Compounds 1, 2, 2-methoxy-6-butyl-1,4-benzoquinone (5), and 2-methoxy-6-decyl-1,4-benzoquinone (6) were tested in two cytotoxicity assays. In the M109 tumor cell lines, quinones 1, 2, and 6 had an IC50 value of 10 mug/mL. In the A2780 cell line, compounds 1, 2 and 5 had IC50 values of 7.9, 2.9, and 3.2 mug/mL, respectively.