pyridinium 1-(ethoxycarbonylacetyl)[ethylthio(thiocarbonyl)]methylide | 333361-29-8

• 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: pyridinium 1-(ethoxycarbonylacetyl)[ethylthio(thiocarbonyl)]methylide
• 英文别名: 5-ethoxy-1-ethylsulfanyl-5-oxo-2-pyridin-1-ium-1-yl-1-sulfanylidenepent-2-en-3-olate
• CAS: 333361-29-8
• 化学式: C₁₄H₁₇NO₃S₂
• 分子量: 311.426
• InChiKey: PKBVDISXQVMWQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  pyridinium 1-(ethoxycarbonylacetyl)[ethylthio(thiocarbonyl)]methylide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 30.0h， 生成 ethyl 3-[(ethylthio)carbonyl]-2-hydroxyindolizine-1-carboxylate
  参考文献：
  名称：

  制备新的氮桥杂环。56.1- [2，2-双（烷硫基）-1-（乙氧基羰基乙酰基）乙烯基]吡啶鎓盐的合成和反应。

  摘要：

  标题化合物很容易从吡啶1- [烷硫基（硫代羰基）]（乙氧羰基乙酰基）亚甲基与烷基卤化物或烷基溴乙酸酯的S-烷基化反应中得到，先用碱处理，然后用脱氢剂处理，得到一些独特的产物，例如3 -[双（烷硫基）亚甲基] -2（3H）-吲哚并酮和二烷基7-甲基-4-氧代-1,4,8,8a-四氢-1,4-噻嗪并[3,4,5-cd]吲哚并嗪-1，5-二羧酸盐。另一方面，在没有脱氢剂的情况下，这些吡啶鎓盐的类似反应提供了2-羟基吲哚嗪-3-羧硫基烷基酯，通过向反应混合物中加入三氟乙酸可以提高其产率。X射线分析证实了某些产物的结构。

  DOI：

  10.1248/cpb.52.1316
• 作为产物：
  描述：

  4-氯乙酰乙酸乙酯 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 37.0h， 生成 pyridinium 1-(ethoxycarbonylacetyl)[ethylthio(thiocarbonyl)]methylide
  参考文献：
  名称：

  Preparation of New Nitrogen-bridged Heterocycles. 50.1 Syntheses of Some Heterocyclic Compounds Starting from Pyridinium 1-(Ethoxycarbonylacetyl)methylides

  摘要：

  The reactions of the title methylides with dialkyl acetylenedicarboxylates gave the corresponding 3-(ethoxycarbonylacetyl)-indolizine derivatives, whose 3-substituent was smoothly converted to a coumarin skeleton by Knoevenagel reaction with salicylaldehyde. The reactions of the methylides with carbon disulfide and alkylating agent in the presence of a base afforded pyridinium 1-[alkylthio(thiocarbonyl)](ethoxycarbonylacetyl)methylides, and the S-alkylations of these ylides with phenacyl bromides and subsequent alkaline treatment of the resulting pyridinium salts gave ethyl 3-alkylthio-1-(arylcarbonyl)thieno[3,4-b]indolizine-9-carboxylates.

  DOI：

  10.3987/com-00-s(i)15

文献信息

• Preparation of New Nitrogen-bridged Heterocycles. 50.1 Syntheses of Some Heterocyclic Compounds Starting from Pyridinium 1-(Ethoxycarbonylacetyl)methylides
  作者：Akikazu Kakehi、Suketaka Ito、Hiroyuki Suga、Katsuaki Yasuraoka

  DOI：10.3987/com-00-s(i)15

  日期：——

  The reactions of the title methylides with dialkyl acetylenedicarboxylates gave the corresponding 3-(ethoxycarbonylacetyl)-indolizine derivatives, whose 3-substituent was smoothly converted to a coumarin skeleton by Knoevenagel reaction with salicylaldehyde. The reactions of the methylides with carbon disulfide and alkylating agent in the presence of a base afforded pyridinium 1-[alkylthio(thiocarbonyl)](ethoxycarbonylacetyl)methylides, and the S-alkylations of these ylides with phenacyl bromides and subsequent alkaline treatment of the resulting pyridinium salts gave ethyl 3-alkylthio-1-(arylcarbonyl)thieno[3,4-b]indolizine-9-carboxylates.
• Preparation of New Nitrogen-Bridged Heterocycles. 56. Syntheses and Reactions of 1-[2,2-Bis(alkylthio)-1-(ethoxycarbonylacetyl)vinyl]pyridinium Salts
  作者：Akikazu Kakehi、Hiroyuki Suga、Yuuya Yamauchi、Katsuaki Yasuraoka、Tomoshige Kobayashi、Akira Ohta

  DOI：10.1248/cpb.52.1316

  日期：——

  The title compounds, readily available from the S-alkylation of pyridinium 1-[alkylthio(thiocarbonyl)](ethoxycarbonylacetyl)methylides with alkyl halides or alkyl bromoacetates, were treated with a base and then a dehydrogenating agent to provide some unique products such as 3-[bis(alkylthio)methylene]-2(3H)-indolizinones and dialkyl 7-methyl-4-oxo-1,4,8,8a-tetrahydro-1,4-thiazino[3,4,5-cd]indolizine-1

  标题化合物很容易从吡啶1- [烷硫基（硫代羰基）]（乙氧羰基乙酰基）亚甲基与烷基卤化物或烷基溴乙酸酯的S-烷基化反应中得到，先用碱处理，然后用脱氢剂处理，得到一些独特的产物，例如3 -[双（烷硫基）亚甲基] -2（3H）-吲哚并酮和二烷基7-甲基-4-氧代-1,4,8,8a-四氢-1,4-噻嗪并[3,4,5-cd]吲哚并嗪-1，5-二羧酸盐。另一方面，在没有脱氢剂的情况下，这些吡啶鎓盐的类似反应提供了2-羟基吲哚嗪-3-羧硫基烷基酯，通过向反应混合物中加入三氟乙酸可以提高其产率。X射线分析证实了某些产物的结构。