1-(2-acetoxyethyl)-3-<(E)-2-(methoxycarbonyl)vinyl>pyridinium bromide | 93630-64-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-(2-acetoxyethyl)-3-<(E)-2-(methoxycarbonyl)vinyl>pyridinium bromide
• 英文别名: methyl (E)-3-[1-(2-acetyloxyethyl)pyridin-1-ium-3-yl]prop-2-enoate;bromide
• CAS: 93630-64-9
• 化学式: Br*C₁₃H₁₆NO₄
• 分子量: 330.178
• InChiKey: BKYJVBWQSXSPEJ-IPZCTEOASA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.27
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-acetoxyethyl)-3-<(E)-2-(methoxycarbonyl)vinyl>pyridinium bromide 在 盐酸 作用下， 以 苯 为溶剂， 生成 methyl (1S,11S,12R,13E)-13-ethylidene-15-(2-hydroxyethyl)-9,15-diazatetracyclo[10.3.1.02,10.03,8]hexadeca-2(10),3,5,7-tetraene-11-carboxylate
  参考文献：
  名称：

  吲哚-2-乙酸烯醇酯亲核加成到N-烷基吡啶鎓盐中。腕足生物碱tubifolidine和tubifoline的正式合成

  摘要：

  报告了一种合成马兜铃生物碱的四环ABCD环亚结构的有效途径，该结构结合了curan系列的C-16氧化的一碳取代基以及nor-curan型生物碱tubifolidine和tubifoline的形式合成。

  DOI：

  10.1016/s0040-4039(00)97813-4
• 作为产物：
  描述：

  2-溴乙基乙酸酯 、 methyl (E)-3-(3-pyridyl)acrylate 生成 1-(2-acetoxyethyl)-3-<(E)-2-(methoxycarbonyl)vinyl>pyridinium bromide
  参考文献：
  名称：

  吲哚生物碱长春花碱的全合成和立体化学重分配

  摘要：

  据报道，吲哚生物碱长春新碱的第一个全合成和该生物碱中碳16处相对构型的重新分配。

  DOI：

  10.1016/0040-4039(84)80023-4

文献信息

• Studies on the synthesis of akuammiline-type alkaloids. Construction of the hexahydro-1,5-methanoazocino[3,4-b)indole fragment
  作者：M.-Lluïsa Bennasar、Ester Zulaica、Manel López、Joan Bosch

  DOI：10.1016/s0040-4039(00)86060-8

  日期：1988.1

  A three step route to the title tetracyclic substructure of akuammiline-type alkaloids consisting in the nucleophilic addition of an ester α-anion to an N-alkylpyridinium salt, acid-induced cyclization of the resultant 1,4-dihydropyridine, and stereoselective elaboration of the ethylidene substituent is reported.

  标题为akuammiline型生物碱的四环亚结构的三步路线，包括将酯α-阴离子亲核加成至N-烷基吡啶鎓盐，酸诱导所得1,4-二氢吡啶的环化反应以及立体选择报道了亚乙基取代基。
• Construction of the pentacyclic ring system of apogeissoschizine
  作者：M. -Lluïsa Bennasar、Ester Zulaica、Bilal A. Sufi、Joan Bosch

  DOI：10.1016/0040-4020(96)00400-0

  日期：1996.6

  The synthesis of pentacyclic apogeissoschizine-type compounds is reported. It involves the construction of the seven-membered E ring by addition of the enolate derived from methyl 1-indolepropionate to the γ-position of a pyridinium salt, with subsequent acid-promoted cyclization of the resulting 1,4-dihydropyridine, and the closure of the C ring by cyclization on the indole 3-position in the last

  已经报道了五环载脂链孢菌素型化合物的合成。它涉及通过将1-吲哚丙酸甲酯衍生的烯酸酯添加到吡啶鎓盐的γ位上来构建七元E环，随后酸促进所得1,4-二氢吡啶的环化反应，并封闭在最后的合成步骤中，通过在吲哚3-位上环化形成C环。
• Synthetic Efforts toward Akuammiline Alkaloids from Tetracyclic 6,7-Seco Derivatives
  作者：M.-Lluïsa Bennasar、Ester Zulaica、Antonio Ramírez、Joan Bosch

  DOI：10.1021/jo951456f

  日期：1996.1.1

  The addition of enolates derived from indole-3-acetic esters 1-3 to pyridinium salts 4, 23, and 24, followed by acid cyclization of the resulting 1,4-dihydropyridines, leads to tetrahydro-1,5-methanoazocino[3,4-b]indoles 5-7, 25-27, which have been subsequently elaborated into 4E-ethylidene(or 4 alpha-ethyl)-hexahydro-1,5-methanoazocino[3,4-b]indoles. Closure of the six-membered C ring of akuammiline alkaloids by formation of C-6/C-7 bond from appropriately N-(b)-substituted derivatives of these tetracyclic ABDE substructures has been extensively investigated. In the N-unsubstituted indole series, both cyclization of thionium ions generated either by Pummerer reaction from sulfoxide 16 or by DMTSF treatment of dithioacetal 36 and photocyclization of chloroacetamide 47 occur upon the indole nitrogen to give pentacycles 18, 38, and 49, respectively. When the indole nitrogen is blocked by a substituent, the thionium ions derived from sulfoxides 17 and 43 and dithioacetals 37 and 44 do not cyclize and lead to different products depending on the reaction conditions, whereas chloroacetamides 48 and 51 undergo a reductive photodehalogenation. Attempted radical cyclization of seleno derivatives 53, 55, and 56 under a variety of conditions gives the corresponding reduced products. Finally, attempted photoisomerization of 1-acylindole 62 leads to the N-(b)-methyl tetracycle 63.
• General method for the synthesis of bridged indole alkaloids. Nucleophilic addition of indoleacetic ester enolates to N-alkylpyridinium salts
  作者：M. Lluisa Bennasar、Mercedes Alvarez、Rodolfo Lavilla、Ester Zulaica、Joan Bosch

  DOI：10.1021/jo00291a013

  日期：1990.2
• BENNASAR, M. -LLUISA;ALVAREZ, MERCEDES;LAVILLA, RODOLFO;ZULAICA, ESTER;BO+, J. ORG. CHEM., 55,(1990) N, C. 1156-1168
  作者：BENNASAR, M. -LLUISA、ALVAREZ, MERCEDES、LAVILLA, RODOLFO、ZULAICA, ESTER、BO+

  DOI：——

  日期：——