retrofractamide A | 94079-67-1

• 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: retrofractamide A
• 英文别名: (2E,4E,8E)-2,4,8-nonatrienamide, 9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)；(2E,4E,8E)-9-(benzo[d][1,3]dioxol-5-yl)-N-isobutylnona-2,4,8-trienamide；retrofractamide-A；retroftactamide A；retrofractamide；(2E,4E,8E)-9-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)nona-2,4,8-trienamide
• CAS: 94079-67-1
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: BPSWISYORIWKCT-FCGWLDPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  retrofractamide A 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 生成 N-isobutyl-9-(3,4-methylenedioxyphenyl)nonanamide
  参考文献：
  名称：

  Retrofractamides-Piper retrofractum 酰胺成分的结构和合成研究

  摘要：

  摘要 从Piper retrofractum 的全部地上部分分离得到两种新的不饱和酰胺，retrofractamides A 和C。光谱和化学研究表明 Retrofractamide A 是 N-isobutyl-9(3',4'-methylenedioxyphenyl)2 E,4 E,8 E-nonatrienamide。反曲霉胺 C 的结构 6 是从光谱和化学研究中提出的，并通过全立体选择性合成得到证实。芝麻素和3,4,5-三甲氧基二氢肉桂酸以及retrofractamide A 的两个高级同系物的存在，即。证明了哌啶（retrofractamide B）和retrofractamide D。也实现了哌啶的合成。

  DOI：

  10.1016/s0031-9422(00)83537-2
• 作为产物：
  描述：

  庚-6-炔醛 在 IrH5(P-(i-Pr)3)2 盐酸 、 氢氧化钾 、 正丁基锂 、 三丁基膦 、 N-phenylphosphoramidochloridate 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 10.25h， 生成 retrofractamide A
  参考文献：
  名称：

  A new methodology to key intermediates for synthesizing polyene compounds

  摘要：

  DOI：

  10.1016/s0040-4020(01)96004-1

文献信息

• Expedient synthesis of unsaturated amide alkaloids from <i>Piper</i> spp: Exploring the scope of recent methodology
  作者：George M. Strunz、Heather J. Finlay

  DOI：10.1139/v96-046

  日期：1996.3.1

  The Sakai aryl aldehyde – cyclic ketone aldol – Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substituents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonal–cyclobutanone aldol-fragmentation product, a hypothetical route to alkaloids such as retrofractamide A, was thus not viable. Instead, three-carbon homologation of the readily available piperonal–cyclopentanone product, using alkyne chemistry recently disclosed by Lu and Trost, afforded these alkaloids in excellent overall yield. The alkyne isomerization was also used to effect efficient syntheses of pellitorine and several other non-aromatic 2E,4E-dienoic Piper amide alkaloids. Key words: Piper, amides, alkaloids, insecticides, aldol, fragmentation, cinnamaldehydes, alkyne, redox, isomerization.

  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。
• Synthesis of retrofractamide A
  作者：Avijit Banerji、Debabrata Bandyopadhyay、Arup K. Siddhanta

  DOI：10.1016/s0031-9422(00)82502-9

  日期：1987.1
• Adipogenetic effects of retrofractamide A derivatives in 3T3-L1 cells
  作者：Ahmed Aboul-Fotouh Mourad、Seikou Nakamura、Tsubasa Ueno、Takahiro Minami、Takanari Yagi、Haruka Yasue、Ryoko Komatsu、Masayuki Yoshikawa、Ashraf Mohamed Taye、Mohamed Ahmed El-Moselhy、Mohamed Montaser Khalifa、Hisashi Matsuda

  DOI：10.1016/j.bmcl.2013.06.101

  日期：2013.9

  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.
• 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.
• BANERJI, AVIJIT;BANDYOPADHYAY, DEBABRATA;SIDDHANTA, ARUP K., PHYTOCHEMISTRY, 26,(1987) N 12, 3345-3346
  作者：BANERJI, AVIJIT、BANDYOPADHYAY, DEBABRATA、SIDDHANTA, ARUP K.

  DOI：——

  日期：——