ethyl 9-(3,4-methylenedioxyphenyl)nona-2E,4E,8E-trienoate | 177555-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: ethyl 9-(3,4-methylenedioxyphenyl)nona-2E,4E,8E-trienoate
• 英文别名: (2E,4E,8E)-9-benzo[1,3]dioxol-5-yl-nona-2,4,8-trienoic acid ethyl ester；ethyl (2E,4E,8E)-9-(1,3-benzodioxol-5-yl)nona-2,4,8-trienoate
• CAS: 177555-26-9
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: UXSFNPFKHRAVHY-FCGWLDPVSA-N

物化性质

• 沸点：
  470.1±44.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 9-(3,4-methylenedioxyphenyl)nona-2E,4E,8E-trienoate 在 palladium on activated charcoal 、 氢气 、 lithium hydroxide 作用下， 生成 N-isobutyl-9-(3,4-methylenedioxyphenyl)nonanamide
  参考文献：
  名称：

  Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells

  摘要：

  In a previous study, retrofractamide A from the fruit of Piper chaba was shown to promote adipogenesis in 3T3-L1 cells. In the present study, retrofractamide A and its derivatives were synthesized, and their adipogenetic effects in 3T3-L1 cells were examined. Among the tested compounds, an amide composed of 9-(3',4'-methylenedioxyphenyl)-nona-2E,4E,8E-trienoic acid and an n-butyl or n-pentyl amine showed strongest activity. Moreover, the amide with the n-pentyl amine moiety significantly increased the uptake of 2-deoxyglucose into the cells, and also increased the mRNA levels of adiponectin, peroxisome proliferator-activated receptor gamma 2 (PPAR gamma 2), glucose transporter 4 (GLUT4), fatty acid-binding protein (aP2), and CCAAT/enhancer-binding protein (C/EBP) alpha and beta in a similar manner as the PPAR gamma agonist troglitazone, although it had less agonistic activity against PPAR gamma. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.101
• 作为产物：
  描述：

  ((E)-5-Oct-1-en-7-ynyl)-benzo[1,3]dioxole 在 正丁基锂 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 49.5h， 生成 ethyl 9-(3,4-methylenedioxyphenyl)nona-2E,4E,8E-trienoate
  参考文献：
  名称：

  Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology

  摘要：

  Sakai芳基醛-环酮Aldol-Grob断裂序列被扩展到肉桂醛和环己酮，并将产物改造为吡啶碱类似物。研究了涉及肉桂醛的反应中取代基的影响。当环辛酮或环丁酮替代环己酮或环戊酮时，苯甲醛无法进行Aldol-断裂序列，对此失败的原因进行了研究。对吡哆醛-环丁酮Aldol-断裂产物进行了四碳Wittig同系化，这是通往碱类如retrofractamide A的假设路线，但该方法并不可行。相反，利用Lu和Trost最近披露的炔化学，对易得的吡哆醛-环戊酮产物进行了三碳同系化，以极高的总产率制备了这些碱类。炔异构化还被用于高效合成辣椒碱和几种其他非芳香2E,4E-二烯酸Piper酰胺类碱类。关键词：Piper、酰胺、碱类、杀虫剂、Aldol、断裂、肉桂醛、炔、氧化还原、异构化。

  DOI：

  10.1139/v96-046

文献信息

• Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors
  作者：Yu Luo、Hao-Min Liu、Ming-Bo Su、Li Sheng、Yu-Bo Zhou、Jia Li、Wei Lu

  DOI：10.1016/j.bmcl.2011.06.046

  日期：2011.8

  Two natural piperamides (piperlonguminine and refrofractamide A) and their derivatives were synthesized and evaluated for inhibitory activity against histone deacetylases, as well as the HCT-116 human colon cancer cell line. The preliminary structure activity relationship was discussed. Compounds featuring a hydroxamic acid moiety exhibited moderate HDAC activity and in vitro cytotoxicity. (C) 2011 Elsevier Ltd. All rights reserved.