3-(α,α-ethyleenedithioethyl)pyridine | 52155-97-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 3-(α,α-ethyleenedithioethyl)pyridine
• 英文别名: 3-(2-methyl-[1,3]dithiolan-2-yl)-pyridine；3-(2-Methyl-[1,3]dithiolan-2-yl)-pyridin；Pyridine, 3-(2-methyl-1,3-dithiolan-2-yl)-；3-(2-methyl-1,3-dithiolan-2-yl)pyridine
• CAS: 52155-97-2
• 化学式: C₉H₁₁NS₂
• 分子量: 197.325
• InChiKey: CABIEQJPGGPJTL-UHFFFAOYSA-N

物化性质

• 沸点：
  330.4±42.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(α,α-ethyleenedithioethyl)pyridine 在 bismuth(III) chloride 、 benzyltriphenylphosphonium peroxymonosulfate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以96%的产率得到3-乙酰基吡啶
  参考文献：
  名称：

  A Convenient Method for Dethioacetalization of 1,3-Dithiolanes and 1,3-Dithianes Using Benzyltriphenylphosphonium Peroxymonosulfate in Aprotic Solvent

  摘要：

  Benzyltriphenylphosphonium peroxymonosulfate in the presence of bismuth chloride was found to be an efficient and mild reagent for the dethioacetalization of 1,3-dithiolanes and 1,3-dithianes to the corresponding carbonyl compounds under aprotic conditions.

  DOI：

  10.1080/10426500214884

文献信息

• Lactams. X. The alkaline ferricyanide oxidation of 3-substituted 1-(3,4-dimethoxyphenethyl)pyridinium salts: Effects of functional substituents.
  作者：TOZO FUJII、MASASHI OHBA、SHIGEYUKI YOSHIFUJI、MAKOTO KIRISAWA

  DOI：10.1248/cpb.25.2887

  日期：——

  In the alkaline ferricyanide oxidation at 32°of 3-substituted 1-(3, 4-dimethoxyphenethyl) pyridinium bromides (type 3), the hydroxymethyl, N, N-dimethylaminomethyl, carbamoyl, and 1, 1-ethylenedithioethyl groups at the 3-position have been found to orient the oxidation to both the 2-(type 4) and the 6-position (type 5) in ratios of 70 : 30, 26 : 74, 50 : 50, and 4 : 96. The carboxyl or 1, 1-ethylenedioxyethyl group at the 3-position has oriented the oxidation to the 6-position exclusively, and possible factors in determining the regioselectivity in the ferricyanide oxidation of the 1, 3-disubstituted pyridinium salts are discussed. For preparation of additional pyridone derivatives, 1-(3, 4-dimethoxyphenethyl)-5-carboxy-2(1H)-pyridone (5d) was esterified with methanolic hydrogen chloride to the methyl ester (5h), and 1-(3, 4-dimethoxyphenethyl)-5-(1, 1-ethylenedioxyethyl)-2 (1H)-pyridone (5e) was converted into the methyl ketone (5i) by acid hydrolysis. The structures of the pyridones (4a, b, c, f, 5a-i) thus prepared have assigned on the basis of their ultraviolet, infrared, and nuclear magnetic resonance spectra.

  在 3-取代的 1-(3,4-二甲氧基苯乙基)吡啶鎓溴化物（类型 3）的 32°碱性铁氰氧化反应中，发现 3-位上的羟甲基、N,N-二甲氨基甲基、氨基甲酰基和 1,1-亚乙基二硫代乙基可将氧化定向到 2-位（类型 4）和 6-位（类型 5），比例分别为 70:30、26:74、50:50 和 4:96。3 位上的羧基或 1，1-亚乙二氧基乙基只将氧化作用定向到 6 位，讨论了决定 1，3-二取代吡啶鎓盐铁氰化物氧化作用区域选择性的可能因素。为了制备更多的吡啶酮衍生物，1-(3, 4-二甲氧基苯乙基)-5-羧基-2(1H)-吡啶酮(5d)被甲醇氯化氢酯化为甲基酯(5h)，1-(3, 4-二甲氧基苯乙基)-5-(1, 1-亚乙二氧基乙基)-2(1H)-吡啶酮(5e)通过酸水解转化为甲基酮(5i)。根据紫外光谱、红外光谱和核磁共振光谱，确定了由此制备的吡啶酮（4a、b、c、f、5a-i）的结构。
• Quinolizidines. XVII. A new access to 9,10-dimethoxy- and 8-hydroxy-9,10-dimethoxybenzo(a)quinolizidine-type Alangium alkaloids from 3-acetylpyridine.
  作者：TOZO FUJII、MASASHI OHBA、SHIGEAKI AKIYAMA

  DOI：10.1248/cpb.33.5316

  日期：——

  New syntheses of the ipecac and Alangium alkaloids possessing the 9, 10-dimethoxy- and 8-hydroxy-9, 10-dimethoxybenzo [a] quinolizidine skeletons (types 1 and 2) have now become possible through generally applicable routes starting from 3-acetylpyridine (5). The routes involve the mercuric acetate-edetic acid oxidation of the 3-acetylpiperidine derivatives 9a, b or the alkaline ferricyanide oxidation of the quaternary salts (26a, b and 27a, b) of 3-acetylpyridine equivalents, Wolff-Kishner reduction of the acetyl group or reductive desulfurization of the thioketal group, sulfenylation-dehydrosulfenylation of the lactams 12a, b, Michael reaction of the α, β-unsaturated lactams 15a, b, and de-ethoxycarbonylation of the Michael adducts 16a, b as the main operations.

  拥有 9，10-二甲氧基和 8-羟基-9，10-二甲氧基苯并[a]喹嗪骨架（类型 1 和 2）的依培康和阿兰生物碱的新合成方法，现在已经可以通过从 3-乙酰基吡啶 (5) 开始的普遍适用的路线来实现。这些方法包括 3-乙酰基哌啶衍生物 9a 和 b 的醋酸乙酸汞氧化法，或 3-乙酰基吡啶等价物的季盐（26a、b 和 27a、b）的碱性铁氰化物氧化法、乙酰基的沃尔夫-基什纳还原或硫酮基的还原脱硫，内酰胺 12a, b 的亚磺酰化-脱氢亚磺酰化，α, β-不饱和内酰胺 15a, b 的迈克尔反应，迈克尔加合物 16a, b 的脱乙氧基羰基化是主要操作。
• Convenient Procedure for Dethioketalisation in Nitrogen Heterocycles
  作者：Venkatachalam S. Giri、Parasurman Jai Sankar

  DOI：10.1080/00397919308011279

  日期：1993.7

  Regeneration of Carbonyl compounds from the corresponding thioketals in nitrogen heterocycles have been effected using Dowex 50W acidic catalyst in reasonable yields.
• Fujii, Tozo; Ohba, Masashi; Sakaguchi, Jun, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 9, p. 3628 - 3640
  作者：Fujii, Tozo、Ohba, Masashi、Sakaguchi, Jun

  DOI：——

  日期：——
• FUJII, TOZO;OHBA, MASASHI;SAKAGUCHI, JUN, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3628-3640
  作者：FUJII, TOZO、OHBA, MASASHI、SAKAGUCHI, JUN

  DOI：——

  日期：——