3-((E)-2-Methoxycarbonyl-vinyl)-1-methyl-pyridinium; iodide | 61859-86-7

• 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-((E)-2-Methoxycarbonyl-vinyl)-1-methyl-pyridinium; iodide
• 英文别名: 3-(3-Methoxy-3-oxoprop-1-en-1-yl)-1-methylpyridin-1-ium iodide；methyl 3-(1-methylpyridin-1-ium-3-yl)prop-2-enoate;iodide
• CAS: 61859-86-7
• 化学式: C₁₀H₁₂NO₂*I
• 分子量: 305.115
• InChiKey: OLJHXSQDCBCNJI-UHFFFAOYSA-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-((E)-2-Methoxycarbonyl-vinyl)-1-methyl-pyridinium; iodide 在 platinum(IV) oxide 氢气 、 sodium methylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 methyl (3S,4R)-4-(2-methoxy-2-oxoethyl)-3-(3-methoxy-3-oxopropyl)-1-methyl-3,4-dihydro-2H-pyridine-5-carboxylate
  参考文献：
  名称：

  制备高度官能化的二氢和四氢吡啶的简短程序

  摘要：

  向3-酰基-1-烷基吡啶鎓盐中添加一系列稳定的碳亲核试剂。然后研究了中间产物二氢吡啶与三氯乙酸酐的酰化作用。由α-（甲基硫烷基）酯烯酸酯的添加所产生的C-4加合物已被转化为合成上有用的1,2,3,4-四氢吡啶。

  DOI：

  10.1016/s0040-4039(99)00621-8

文献信息

• Regioselective Synthesis of Indolyldihydropyridines. A Remarkable Solvent Effect
  作者：Rodolfo Lavilla、Teresa Gotsens、Joan Bosch

  DOI：10.1055/s-1991-26587

  日期：——

  The synthesis of 1,2-dihydro-2-(3-indolyl)-1-methylpyridines and 1,4-dihydro-4-(3-indolyl)-1-methylpyridines through the addition of indoles to pyridinium salts in various solvents is described. Selective preparation of 1,2-dihydropyridines is possible performing the reaction in methanol as the solvent, whereas the 1,4-isomers are preferentially formed in dimethyl sulfoxide.

  介绍了在不同溶剂中通过吲哚与吡啶鎓盐的加成反应合成 1,2-二氢-2-(3-吲哚基)-1-甲基吡啶和 1,4-二氢-4-(3-吲哚基)-1-甲基吡啶的方法。 以甲醇为溶剂进行反应可以选择性地制备 1,2-二氢吡啶，而 1,4-异构体则优先在二甲亚砜中生成。
• Alstoscholarisines H–J, Indole Alkaloids from <i>Alstonia scholaris</i>: Structural Evaluation and Bioinspired Synthesis of Alstoscholarisine H
  作者：Zhiqiang Pan、Xu-Jie Qin、Ya-Ping Liu、Ting Wu、Xiao-Dong Luo、Chengfeng Xia

  DOI：10.1021/acs.orglett.5b03583

  日期：2016.2.19

  Alstoscholarisines H–J (1–3), new monoterpenoid indole alkaloids with an unprecedented skeleton created via the formation of a C-3/N-1 bond, were isolated from Alstonia scholaris. Their structures were established by extensive spectroscopic analyses and the assessment of single-crystal X-ray diffraction data. The total synthesis of alstoscholarisine H was achieved via the regioselective nucleophilic addition

  Alstoscholarisines H-Ĵ（1 - 3），单萜新吲哚生物碱经由C-3 / N-1键的形成创造了前所未有的骨架，从分离灯台树。通过广泛的光谱分析和对单晶X射线衍射数据的评估，确定了它们的结构。alstoscholarisine H的总合成是通过吡啶的区域选择性亲核加成反应实现的，该吡啶鎓是通过生物启发的亚胺离子中间体，然后进行Pictet-Spengler样环化而形成的。
• Nucleophilic addition of 2-indolylacyl anion equivalents to N-alkylpyridinium salts
  作者：M. Lluisa Bennasar、Ester Zulaica、Joan Bosch

  DOI：10.1021/jo00036a015

  日期：1992.5

  The reactions of the anions derived from dithioacetals 1-3 and a-amino nitriles 4 toward pyridinium salts 5 are studied. Depending on the nucleophile used, 2-(dihydropyridylmethyl)indoles 6 and 7, which can be cyclized to tetracyclic methanoazocinindole systems 10 and 11, respectively, or 2-substituted 3-(dihydropyridyl)indoles 8 and 9 are formed.
• A short procedure for the preparation of highly functionalized di- and tetrahydropyridines
  作者：M.-Lluïsa Bennasar、Ester Zulaica、Cecília Juan、Laura Llauger、Joan Bosch

  DOI：10.1016/s0040-4039(99)00621-8

  日期：1999.5

  The addition of a series of stabilized carbon nucleophiles to 3-acyl-1-alkylpyridinium salts. followed by acylation of the intermediate dihydropyridines with trichloroacetic anhydride has been studied. The C-4 adducts resulting from the addition of α-(methylsulfanyl)ester enolates have been converted into synthetically useful 1,2,3,4-tetrahydropyridines.

  向3-酰基-1-烷基吡啶鎓盐中添加一系列稳定的碳亲核试剂。然后研究了中间产物二氢吡啶与三氯乙酸酐的酰化作用。由α-（甲基硫烷基）酯烯酸酯的添加所产生的C-4加合物已被转化为合成上有用的1,2,3,4-四氢吡啶。