(2E,4E,6E)-7-(2-thienyl)-2,4-6-heptatrienoic acid piperidide | 52657-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2E,4E,6E)-7-(2-thienyl)-2,4-6-heptatrienoic acid piperidide
• 英文别名: 1-[(2E,4E,6E)-7-(2-thienyl)-2,4,6-heptatrienoyl]piperidine；1-[(2E,4E,6E)-1-oxo-7-(2-thienyl)heptatrienyl]piperidine；7-(thiophene)-2E,4E,6E-heptatrienoic acid piperidide；Otanthus Maritima amide；N-piperidineotanthusic acid amide；Otanthussaeure-piperidid；(2E,4E,6E)-1-piperidin-1-yl-7-thiophen-2-ylhepta-2,4,6-trien-1-one
• CAS: 52657-10-0
• 化学式: C₁₆H₁₉NOS
• 分子量: 273.399
• InChiKey: IOXFTHWVGPAEOG-DEVQJBAHSA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  484.9±24.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(溴乙酰基)哌啶 在 potassium carbonate 作用下， 以 乙腈 、 苯 为溶剂， 反应 6.0h， 生成 (2E,4E,6E)-7-(2-thienyl)-2,4-6-heptatrienoic acid piperidide
  参考文献：
  名称：

  （2E）-，（2E，4E）-不饱和酰胺和相关天然产物的简便且高度立体选择性的合成

  摘要：

  通过具有高立体选择性的溴化砷可以轻松合成（2E）-，（2E，4E）-不饱和酰胺。还报道了其在相关天然产物4和5的合成中的应用。

  DOI：

  10.1016/s0040-4039(00)96069-6

文献信息

• Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg–Bäcklund reaction
  作者：Yang Li、Yu Zhang、Zhi Huang、Xiaoping Cao、Kun Gao

  DOI：10.1139/v04-028

  日期：2004.5.1

  A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a–1n by the recently developed one-flask Ramberg–Backlund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide

  描述了一种通过最近开发的单瓶 Ramberg??Backlund 反应合成天然存在的不饱和酰胺生物碱 1a??1n 的方便快捷的方法。起始原料是醇 3，使用 Mitsunobu 反应将其转化为硫代乙酸酯 4。4 的乙酰基部分的原位裂解，然后用合适的氯乙酰胺 5 将所得硫醇烷基化，提供硫化物 6。硫化物 6 氧化得到相应的砜 2。在氧化铝-存在下用二溴二氟甲烷处理砜 2二氯甲烷溶液中负载的氢氧化钾得到不饱和酰胺生物碱1a??1n。据我们所知，1e和1i的合成是首次报道。关键词：合成，不饱和酰胺生物碱，Ramberg??Backlund反应。
• Stereoselective Synthesis of Naturally-Occurring 7-(Hetero) Aryl (2E, 4E, 6E)-2, 4, 6-Heptatrienamides and Their Structural Analogues
  作者：Renzo Rossi、Adriano Carpita、Vito Lippolis

  DOI：10.1080/00397919108016755

  日期：1991.2

  A new and efficient highly stereoselective method to prepare naturally-occurring 7-(hetero)aryl (2E,4E,6E)-2,4,6-heptatrienamides and their structural analogues has been developed. The physical and spectral properties of one of these compounds, i.e. (2E,4E,6E)-7-(2-thienyl)-2,4,6-heptatrienoic acid piperidide (4 b), have been found to be quite different from those previously reported for 7-(2-thienyl)-2,4,6-heptatrienoic acid piperidide isolated from Othantus maritimus to which the (2E,4E,6E)-configuration had been previously assigned.
• A Very Short and Efficient Total Synthesis of Otanthus Maritima Amide.
  作者：Moncef Bellassoued、Malika Salemkour、Emmanuelle Reboul

  DOI：10.1080/00397919708005016

  日期：1997.9

  A new total synthesis of Otanthus Maritima amide 1 was achieved from 6-trimetylsily N-tert-butyl sorbaldimine 6 in 76% global yield. The natural product 1 was obtained in three steps by condensation of 6 on thiophenal in the presence of catalytic amount of CsF (10%) in DMSO followed by oxidation and amidification of the corresponding intermediate.
• YANG, JIAN-HUA;SHI, LI-LAN;XIAO, WEN-JUAN;WEN, XUE-QING;HUANG, YAO-ZENG, HETEROATOM CHEM., 1,(1990) N, C. 75-81
  作者：YANG, JIAN-HUA、SHI, LI-LAN、XIAO, WEN-JUAN、WEN, XUE-QING、HUANG, YAO-ZENG

  DOI：——

  日期：——
• ROSSI, RENZO;CARPITA, ADRIANO;LIPPOLIS, VITO, SYNTH. COMMUN., 21,(1991) N, C. 333-349
  作者：ROSSI, RENZO、CARPITA, ADRIANO、LIPPOLIS, VITO

  DOI：——

  日期：——