3-<2-(methoxycarbonyl)vinyl>piridinium iodide | 119219-77-1

• 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: 3-<2-(methoxycarbonyl)vinyl>piridinium iodide
• 英文别名: methyl (E)-3-(1-methylpyridin-1-ium-3-yl)prop-2-enoate;iodide
• CAS: 119219-77-1
• 化学式: C₁₀H₁₂NO₂*I
• 分子量: 305.115
• InChiKey: OLJHXSQDCBCNJI-IPZCTEOASA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<2-(methoxycarbonyl)vinyl>piridinium iodide 在 platinum(IV) oxide 三甲基硅基二氢化磷酸酯 、 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 9.55h， 生成 methyl cis-7-benzyl-2-methyl-6,12-dioxo-3,4,4a,5,6,12-hexahydro-2H-pyrido[3',4':4,5]cyclohepta[1,2-b]indole-4-propionate
  参考文献：
  名称：

  A Synthetic Entry to Ervatamine Alkaloids − Synthesis of (±)-6-Oxo-16-episilicine and (±)-6-Oxosilicine

  摘要：

  Catalytic hydrogenation of several 3-acyl-4-[2-(indolyl)carbonylmethyl]-5-(methoxycarbonyl)-1,4-dihydropyridines 4 gives chemoselectively the corresponding 1,2,3,4-tetrahydropyridyl esters 5, which have been elaborated into the tetracyclic 2,3-diacylindole system 6 of oxosilicine alkaloids. Barton decarboxylation of the N-benzyl derivative 6e, followed by debenzylation and subsequent stereoselective reduction of the 5,16-double bond gives (+/-)-6-oxo-16-episilicine. This compound is converted into (+/-)-6-oxosilicine by base-catalyzed epimerization.

  DOI：

  10.1002/1099-0690(200012)2000:23<3919::aid-ejoc3919>3.0.co;2-p

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。
• A straightforward entry to the ervitsine skeleton. Synthesis of 16-demethyleneervitsine
  作者：M.-Lluisa Bennasar、Ester Zulaica、Bernat Vidal、Joan Bosch

  DOI：10.1016/s0040-4039(00)74813-1

  日期：1992.6

  A short synthetic route to 16-demethyleneervitsine (6), based on the nucleophilic addition of 2-acetylindole enolates to N-alkyl-β-acylpyridinium salts and further acid cyclization of the resulting 1,4-dihydropyridine intermediates, is reported.

  据报道，基于2-乙酰基吲哚烯酸酯向N-烷基-β-酰基吡啶鎓盐的亲核加成以及所得1,4-二氢吡啶中间体的进一步酸环化，合成16-脱亚甲基维他命（6）的短途径。
• 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。
• A short synthesis of N (a)-methylervitsine. Reactivity of the intermediate 1,4-dihydropyridine towards electrophiles
  作者：M. Lluisa Bennasar、Bernat Vidal、Joan Bosch

  DOI：10.1039/c39950000125

  日期：——

  A four-step synthesis of N(a)-methylervitsine involving the nucleophilic addition of the enolate derived from acetylindole 2 to pyridinium salt 3, with subsequent C6H5SeBr-promoted cyclization of the resulting 1,4-dihydropyridine and further elaboration of the exocyclic 20E-ethylidene and 16-methylene substituents, is reported.

  报告称,N(a)-methylvitsine的四步合成涉及从 acetylindole 2 衍生的核酸酸盐添加到 pyridinium 盐3中,随后由 C6H5SeBr 促进生成 1,4-dihydropyridine 的循环化,并进一步研制异循环的 20E-ethylidene 和 16-methylene 替代品。
• 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