3-(octyloxy)-4-methoxybenzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(octyloxy)-4-methoxybenzaldehyde
• 英文别名: 3-(Octyloxy)-4-methoxy benzaldehyde；4-methoxy-3-octoxybenzaldehyde
• 化学式: C₁₆H₂₄O₃
• mdl: MFCD06742802
• 分子量: 264.365
• InChiKey: PMIYSJQXBJTQSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.562
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(octyloxy)-4-methoxybenzaldehyde 在 sodium tetrahydroborate 作用下， 反应 0.5h， 以72%的产率得到(4-Methoxy-3-octoxyphenyl)methanol
  参考文献：
  名称：

  Understanding the cytotoxic effects of new isovanillin derivatives through phospholipid Langmuir monolayers

  摘要：

  Twenty-one isovanillin derivatives were prepared in order to evaluate their cytotoxic properties against the cancer cell lines B16F10-Nex2, HL-60, MCF-7, A2058 and HeLa. Among them, seven derivatives exhibited cytotoxic activity. We observed that for obtaining smaller IC50, values and for increasing the index of selectivity, two structural features are very important when compared with isovanillin (1); a hydroxymethyl group at C-1 and the replacement of the hydroxyl group at C-3 by different alkyl groups. As the lipophilicity of the compounds was changed, we decided to investigate the interaction of the cytotoxic isovallinin derivatives on cell membrane models through Langmuir monolayers by employing the lipids DPPC (1,2-diplamitoyl-sn-glycero-3-phosphocoline) and DPPS (1,2-diplamitoyl-sn-glycero-3-phosphoserine). The structural changes on the scaffold of the compounds modulated the interaction with the phospholipids at the air-water interface. These results were very important to understand the biophysical aspects related to the interaction of the cytotoxic compounds with the cancer cell membranes.

  DOI：

  10.1016/j.bioorg.2018.10.029
• 作为产物：
  描述：

  异香兰素 、 1-溴辛烷 在 potassium carbonate 、 N,N'-didodecyl-N,N,N',N'-tetramethyl-N,N'-(p-xylenediyl)diammonium dibromide 作用下， 以 四氢呋喃 为溶剂， 反应 13.5h， 以79%的产率得到3-(octyloxy)-4-methoxybenzaldehyde
  参考文献：
  名称：

  季铵型双子表面活性剂的相转移催化：异香草醛的O-烷基化

  摘要：

  在本文中，O描述了用不常见的相转移催化剂对异香草醛进行烷基化的烷基二α-α，ω-双（二甲基烷基溴化铵）二聚表面活性剂（也称为双子表面活性剂）。在我们的实验室中，合成并表征了一些具有简单疏水烷基链的二聚表面活性剂和其他一些具有不同长度的酯官能团的疏水烷基链。异香草醛与烷基卤的烷基化在碳酸钾和相转移催化剂存在下于四氢呋喃中连续进行。使用传统的相转移催化剂四丁基溴化铵和不使用任何催化剂也进行了相同的反应。将结果与二聚表面活性剂进行比较。因此，有人表示烷烃基α，ω-双（二甲基烷基溴化铵）二聚表面活性剂在温和的条件下通过环境友好的方法连续显示出相转移催化剂的特性。这项工作最重要的特点是，已确定二聚表面活性剂可以用作相转移剂。

  DOI：

  10.1007/s11743-016-1821-z

文献信息

• Phase Transfer Catalysis with Quaternary Ammonium Type Gemini Surfactants: O-Alkylation of Isovanillin
  作者：Mesut Boz、Sedat Semih Baştürk

  DOI：10.1007/s11743-016-1821-z

  日期：2016.7

  alkylation of isovanillin with alkyl halide was successively carried out in the presence of potassium carbonate and a phase transfer catalyst in tetrahydrofuran. The same reactions were also performed with both the traditional phase transfer catalyst tetrabutylammonium bromide and without any catalyst. The results were compared with those of dimeric surfactants. Consequently, it was expressed that alkandiyl‐α

  在本文中，O描述了用不常见的相转移催化剂对异香草醛进行烷基化的烷基二α-α，ω-双（二甲基烷基溴化铵）二聚表面活性剂（也称为双子表面活性剂）。在我们的实验室中，合成并表征了一些具有简单疏水烷基链的二聚表面活性剂和其他一些具有不同长度的酯官能团的疏水烷基链。异香草醛与烷基卤的烷基化在碳酸钾和相转移催化剂存在下于四氢呋喃中连续进行。使用传统的相转移催化剂四丁基溴化铵和不使用任何催化剂也进行了相同的反应。将结果与二聚表面活性剂进行比较。因此，有人表示烷烃基α，ω-双（二甲基烷基溴化铵）二聚表面活性剂在温和的条件下通过环境友好的方法连续显示出相转移催化剂的特性。这项工作最重要的特点是，已确定二聚表面活性剂可以用作相转移剂。
• Understanding the cytotoxic effects of new isovanillin derivatives through phospholipid Langmuir monolayers
  作者：Ana C. de Carvalho、Natália Girola、Carlos R. de Figueiredo、André C. Machado、Lívia S. de Medeiros、Rafael C. Guadagnin、Luciano Caseli、Thiago A.M. Veiga

  DOI：10.1016/j.bioorg.2018.10.029

  日期：2019.3

  Twenty-one isovanillin derivatives were prepared in order to evaluate their cytotoxic properties against the cancer cell lines B16F10-Nex2, HL-60, MCF-7, A2058 and HeLa. Among them, seven derivatives exhibited cytotoxic activity. We observed that for obtaining smaller IC50, values and for increasing the index of selectivity, two structural features are very important when compared with isovanillin (1); a hydroxymethyl group at C-1 and the replacement of the hydroxyl group at C-3 by different alkyl groups. As the lipophilicity of the compounds was changed, we decided to investigate the interaction of the cytotoxic isovallinin derivatives on cell membrane models through Langmuir monolayers by employing the lipids DPPC (1,2-diplamitoyl-sn-glycero-3-phosphocoline) and DPPS (1,2-diplamitoyl-sn-glycero-3-phosphoserine). The structural changes on the scaffold of the compounds modulated the interaction with the phospholipids at the air-water interface. These results were very important to understand the biophysical aspects related to the interaction of the cytotoxic compounds with the cancer cell membranes.