4-(2,6,10-trimethyl-1,3,5,9-undecatetraenyl)benzoic acid | 161695-17-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-(2,6,10-trimethyl-1,3,5,9-undecatetraenyl)benzoic acid
• 英文别名: 4-[(1E,3E,5E)-2,6,10-trimethylundeca-1,3,5,9-tetraenyl]benzoic acid
• CAS: 161695-17-6
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: QVNMGMBKZGQNEZ-JOWUDUDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2,6,10-trimethyl-1,3,5,9-undecatetraenyl)benzoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以84%的产率得到p-(2,6,10-trimethylundecyl)benzoic acid
  参考文献：
  名称：

  乙基-(2-甲基-3-氧代丙基)-和对-(2-甲基-3-氧代-1-丙烯基)苯甲酸酯：制备和用于合成对-(正聚异戊二烯基)苯甲酸的生物活性衍生物

  摘要：

  已开发出制备标题化合物的新方法。饱和 (1) 和不饱和 (2) 醛酯，它们很容易通过 Pd 催化的 4-溴苯甲酸乙酯与甲烯丙醇的反应以及 4-甲酰基苯甲酸乙酯与丙醛的羟醛缩合反应而获得，它们是具有战略意义的中间体，可用于合成。将一些合成化合物的体外试验结果与其体内药理作用的已知数据进行比较。

  DOI：

  10.1007/bf00698894
• 作为产物：
  描述：

  (E)-methyl 3-(4-formylphenyl)-2-methylacrylate 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 高氯酸 、 水 、 silica gel 、 potassium carbonate 、 pyridinium chlorochromate 、 silver(l) oxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 4-(2,6,10-trimethyl-1,3,5,9-undecatetraenyl)benzoic acid
  参考文献：
  名称：

  A novel approach to the synthesis of benzoic and cinnamic acid derivatives with nor-isoprenoid substituents

  摘要：

  A novel strategy for the synthesis of 4-(nor-polyprenyl)-substituted benzoic acids and their esters of the general formula 1 as well as their vinylogs of the type 2, based on the use of terephthalic aldehyde (3) and its tetramethyl acetal (13), is elaborated. The carbonyl groups in dialdehydes 3 and 12 can be selectively involved in the reaction sequences leading to the introduction of both aliphatic and functional substituents in positions 1 and 4 of the benzene ring.

  DOI：

  10.1007/bf00698948

文献信息

• The synthesis of 4-(2,6,10-trimethyl-1,3,5,9-undecatetraenyl)benzoic acid based on alkoxy alkene-acetal condensation
  作者：G. V. Kryshtal'、G. M. Zhdankina、E. P. Serebryakov

  DOI：10.1007/bf00698949

  日期：1993.5

  10-Trimethyl-1,3,5,9-undecatetraenyl)benzoic acid (1) was synthesized starting from ethyl 4-formylbenzoate (2) and linalool. The key intermediate, ethyl 4-(2-methyl-3-oxo-1-propenyl)benzoate (5), was obtained by the addition of diethyl acetal (3), prepared from2, to ethyl 1-propenyl ether (EPE) followed by the hydrolysis of the resulting adduct.

  摘要 以 4-甲酰基苯甲酸乙酯 (2) 和芳樟醇为原料合成了 4-(2,6,10-三甲基-1,3,5,9-十一碳四烯基)苯甲酸 (1)。关键中间体 4-(2-甲基-3-氧代-1-丙烯基)苯甲酸乙酯 (5) 通过将由 2 制备的乙缩醛 (3) 添加到 1-丙烯基醚 (EPE) 中，然后通过所得加合物的水解。
• US4482734A
  申请人：——

  公开号：US4482734A

  公开（公告）日：1984-11-13
• A novel approach to the synthesis of benzoic and cinnamic acid derivatives with nor-isoprenoid substituents
  作者：G. V. Kryshtal'、G. M. Zhdankina、E. P. Serebryakov

  DOI：10.1007/bf00698948

  日期：1993.5

  A novel strategy for the synthesis of 4-(nor-polyprenyl)-substituted benzoic acids and their esters of the general formula 1 as well as their vinylogs of the type 2, based on the use of terephthalic aldehyde (3) and its tetramethyl acetal (13), is elaborated. The carbonyl groups in dialdehydes 3 and 12 can be selectively involved in the reaction sequences leading to the introduction of both aliphatic and functional substituents in positions 1 and 4 of the benzene ring.
• Ethylp-(2-methyl-3-oxopropyl)- andp-(2-methyl-3-oxo-1-propenyl)benzoates: preparation and use in the synthesis of biologically active derivatives ofp-(nor-polyprenyl)benzoic acids
  作者：G. V. Kryshtal'、G. M. Zhdankina、E. P. Serebryakov

  DOI：10.1007/bf00698894

  日期：1993.12

  Novel ways for preparing the title compounds have been developed. Saturated (1) and unsaturated (2) aldehydoesters, which are easily accessible by a Pd-catalyzed reaction of ethyl 4-bromobenzoate with methallyl alcohol and aldol condensation of ethyl 4-formyl-benzoate with propanal, respectively, are strategically advantageous intermediates for the synthesis. The results of thein vitro assays of some

  已开发出制备标题化合物的新方法。饱和 (1) 和不饱和 (2) 醛酯，它们很容易通过 Pd 催化的 4-溴苯甲酸乙酯与甲烯丙醇的反应以及 4-甲酰基苯甲酸乙酯与丙醛的羟醛缩合反应而获得，它们是具有战略意义的中间体，可用于合成。将一些合成化合物的体外试验结果与其体内药理作用的已知数据进行比较。