1,2,4-trimethoxy-5-n-pentylbenzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2,4-trimethoxy-5-n-pentylbenzene
• 英文别名: 1,2,4-trimethoxy-5-pentylbenzene
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: NTKCKBHCNPVXJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,4-trimethoxy-5-n-pentylbenzene 在 三甲基氯硅烷 、 四甲基乙二胺 、 仲丁基锂 、 三溴化硼 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 水 、 乙腈 为溶剂， 反应 8.67h， 生成 6-methyl-5-pentylbenzene-1,2,4-triol
  参考文献：
  名称：

  Alkylbenzoquinone Involved in Development of Cellular Slime Molds

  摘要：

  The structure of the prespore-cell-promoting factor from Dictyostelium discoideum was determined to be 2-hydroxy-5-methyl-6-pentylbenzoquinone. The synthetic compound has prespore-cell-promoting activity similar to the natural one, with half-maximal induction at a concentration as low as 40 pM. It was also found that the factor induces aggregation in an aggregation-deficient mutant of a related species, Polysphodilium violaceum. Both these activities are sensitive to positional isomerism with the 6-methyl-5-pentyl isomer showing no detectable activity.

  DOI：

  10.1021/ol5014119
• 作为产物：
  描述：

  2,4,5-三甲氧基苯甲酸 在 三乙基硅烷 、 四丙基高钌酸铵 、 硼烷四氢呋喃络合物 、 三氟甲磺酸三甲基硅酯 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 1,2,4-trimethoxy-5-n-pentylbenzene
  参考文献：
  名称：

  Alkylbenzoquinone Involved in Development of Cellular Slime Molds

  摘要：

  The structure of the prespore-cell-promoting factor from Dictyostelium discoideum was determined to be 2-hydroxy-5-methyl-6-pentylbenzoquinone. The synthetic compound has prespore-cell-promoting activity similar to the natural one, with half-maximal induction at a concentration as low as 40 pM. It was also found that the factor induces aggregation in an aggregation-deficient mutant of a related species, Polysphodilium violaceum. Both these activities are sensitive to positional isomerism with the 6-methyl-5-pentyl isomer showing no detectable activity.

  DOI：

  10.1021/ol5014119

文献信息

• Cruz, Adriana; Garduno, Leticia; Salazar, Maria, Medicinal Chemistry Research, 2001, vol. 10, # 9, p. 587 - 595
  作者：Cruz, Adriana、Garduno, Leticia、Salazar, Maria、Martinez, Elizdath、Diaz, Francisco、Chamorro, German、Tamariz, Joaquin

  DOI：——

  日期：——
• Alkylbenzoquinone Involved in Development of Cellular Slime Molds
  作者：Yoshiaki Takaya、Rie Hotta、Kenshu Fujiwara、Risa Otani、Yurika Uchiyama、Mizuki Sakakibara、Eri Fukuda、Masatake Niwa、Kei Inouye、Akiko A. Oohata

  DOI：10.1021/ol5014119

  日期：2014.7.18

  The structure of the prespore-cell-promoting factor from Dictyostelium discoideum was determined to be 2-hydroxy-5-methyl-6-pentylbenzoquinone. The synthetic compound has prespore-cell-promoting activity similar to the natural one, with half-maximal induction at a concentration as low as 40 pM. It was also found that the factor induces aggregation in an aggregation-deficient mutant of a related species, Polysphodilium violaceum. Both these activities are sensitive to positional isomerism with the 6-methyl-5-pentyl isomer showing no detectable activity.