3-庚基-1,2-苯二酚 | 117788-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 3-庚基-1,2-苯二酚
• 英文名称: 3-heptylcatechol
• 英文别名: 3-heptylbenzene-1,2-diol；3-heptyl-pyrocatechol；2.3-Dihydroxy-1-heptyl-benzol；3-Heptyl-brenzcatechin
• CAS: 117788-50-8
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: VDSNRFLNTUUEME-UHFFFAOYSA-N

物化性质

• 沸点：
  332.7±22.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-furan-2-ylnonan-1-ol 在 palladium on activated charcoal 盐酸 、 manganese(IV) oxide 、 氢气 、 lithium perchlorate 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 苯 为溶剂， 25.0~45.0 ℃ 、101.33 kPa 条件下， 反应 52.0h， 生成 3-庚基-1,2-苯二酚
  参考文献：
  名称：

  Synthesis of 3-Alkylcatechols via Intramolecular Cyclization

  摘要：

  描述了2-烷酰基-2,5-二甲氧基四氢呋喃4与水性酸的分子内环化反应。通过在1M盐酸存在下煮沸化合物4的二恶烷溶液，通常能够获得3-烷基儿茶酚7，产率良好。此外，当化合物4的二恶烷溶液用0.1 M盐酸处理时，还能获得良到高产率的4,5-二氧代烷醛6。

  DOI：

  10.1055/s-1990-26889

文献信息

• Scope and Limitations of Lithium-Ethylenediamine-THF-Mediated Cleavage at the α-Position of Aromatics: Deprotection of Aryl Methyl Ethers and Benzyl Ethers under Mild Conditions
  作者：Takeshi Sugai、Takeyuki Shindo、Yasuaki Fukuyama

  DOI：10.1055/s-2004-815977

  日期：——

  and limitation of lithium-ethylenediamine-THF-mediated reductive bond cleavage at the α-position of aromatics were examined. Very mild conditions such as lithium metal (5 equiv) and ethylenediamine (7 equiv) in oxygen-free THF were quite effective for the demethylation of aromatic ethers even at as low as -10 °C. Allyl benzyl ethers were also deprotected under these conditions with very little change

  考察了锂-乙二胺-THF介导的芳烃α位还原键断裂的范围和局限性。即使在低至 -10 °C 的条件下，无氧 THF 中的锂金属（5 equiv）和乙二胺（7 equiv）等非常温和的条件对芳族醚的去甲基化也非常有效。烯丙基苄基醚也在这些条件下脱保护，烯丙醇部分几乎没有变化。通过这项研究，开发了 2,6-二甲基苄基 (m-xylylmethyl, MXM) 基团作为苄基的替代物，在上述还原条件下易于裂解。
• A quantitative structure-activity relationship for antitumor activity of long-chain phenols from Ginkgo biloba L.
  作者：Hideji ITOKAWA、Nobuo TOTSUKA、Keisuke NAKAHARA、Manaby MAEZURU、Koichi TAKEYA、Miyuki KONDO、Mutsumi INAMATSU、Hiroshi MORITA

  DOI：10.1248/cpb.37.1619

  日期：——

  With the aim of obtaining compounds with strong antitumor activity, a quantitative structure-activity relationship (QSAR) of antitumor phenolic compounds (long-chain phenols) was derived using the Hansch-Fujita equation. The ED50 values against Chinese hamster V-79 cells were analyzed in terms of log P as the hydrophobic parameter and the energy of the lowest unoccupied molecular orbital (ELUMO) calculated by using the modified neglect of differential overlap (MNDO) method as the electronic parameter, by means of multiple regression analysis. It was found that the activities mainly depended on log P (an optimum log P of 8.3) and a low-lying ELUMO value. 4-Undecylcatechol, selected on the basis of the above results, exhibited strong antitumor activity against Sarcoma 180 ascites and P-388 lymphocytic leukemia.

  为了获得具有强抗肿瘤活性的化合物，利用Hansch-Fujita方程导出了抗肿瘤酚类化合物（长链酚）的定量构效关系（QSAR）。通过多重回归分析，分析了针对中国仓鼠V-79细胞的ED50值，考虑了疏水参数log P和通过改良的差分重叠忽略（MNDO）方法计算的最低未占分子轨道能量（ELUMO）作为电子参数。研究发现，活性主要依赖于log P（最佳log P为8.3）和较低的ELUMO值。基于上述结果选择的4-十一烷基儿茶酚，对肉瘤180腹水和P-388淋巴细胞白血病展现出了强抗肿瘤活性。
• 215. Some derivatives of catechol and pyrogallol. Part I
  作者：Robert D. Haworth、David Woodcock

  DOI：10.1039/jr9460000999

  日期：——
• US4011181A
  申请人：——

  公开号：US4011181A

  公开（公告）日：1977-03-08
• Synthesis of 3-Alkylcatechols via Intramolecular Cyclization
  作者：Tetsuo Miyakoshi、Hiroyasu Togashi

  DOI：10.1055/s-1990-26889

  日期：——

  The intramolecular cyclization of 2-alkanoyl-2,5-dimethoxytetrahydrofurans 4 with aqueous acid is described. 3-Alkylcatechols 7 were prepared in generally good yields by boiling the dioxane solution of compounds 4 in the presence of 1M hydrochloric acid. In addition, 4,5-dioxoalkanals 6 were obtained in good to high yields when the dioxane solution of compounds 4 was treated with 0.1 M hydrochloric acid.

  描述了2-烷酰基-2,5-二甲氧基四氢呋喃4与水性酸的分子内环化反应。通过在1M盐酸存在下煮沸化合物4的二恶烷溶液，通常能够获得3-烷基儿茶酚7，产率良好。此外，当化合物4的二恶烷溶液用0.1 M盐酸处理时，还能获得良到高产率的4,5-二氧代烷醛6。