ethyl 1-benzoyl-7-methyl-3-(methylthio)thieno[3,4-b]indolizine-9-carboxylate | 333361-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 1-benzoyl-7-methyl-3-(methylthio)thieno[3,4-b]indolizine-9-carboxylate
• 英文别名: Ethyl 3-benzoyl-6-methyl-1-methylsulfanylthieno[3,4-b]indolizine-4-carboxylate
• CAS: 333361-36-7
• 化学式: C₂₂H₁₉NO₃S₂
• 分子量: 409.53
• InChiKey: RUWMHNFHQXLGJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-benzoyl-7-methyl-3-(methylthio)thieno[3,4-b]indolizine-9-carboxylate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以93%的产率得到1-(Hydroxy-phenyl-methyl)-6-methyl-3-methylsulfanyl-2-thia-3b-aza-cyclopenta[a]indene-8-carboxylic acid ethyl ester
  参考文献：
  名称：

  新型氮桥杂环的制备。69. 1-(α-Hydroxybenzyl)thieno [3,4-b] indolizine 衍生物的合成与反应

  摘要：

  通过在回流乙醇中用硼氢化钠还原相应的 l-苯甲酰基噻吩并 [3,4-6] 吲哚腙，以良好的收率获得标题化合物，即 l-(α-羟基苄基) 噻吩并 [3,4-o] 吲哚嗪衍生物. 这些化合物相当不稳定，即使在室温下也逐渐分解，但是，在暴露于乙酸时，会发生意想不到的缩合反应，在低至中等浓度下得到 a,]indolizin-l-yl) 甲苯

  DOI：

  10.1515/hc.2010.16.1.53
• 作为产物：
  描述：

  (E)-[3-(2-ethoxy-2-oxoethyl)-4-(4-methylpyridin-1-ium-1-yl)-5-sulfanylidenethiophen-2-ylidene]-phenylmethanolate 在 四氯苯醌 、 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 12.25h， 生成 ethyl 1-benzoyl-7-methyl-3-(methylthio)thieno[3,4-b]indolizine-9-carboxylate
  参考文献：
  名称：

  制备新的氮桥杂环。53. 3-（苄硫基）噻吩并[3,4-b]吲哚嗪衍生物的合成及其分子内芳烃-芳烃相互作用。

  摘要：

  通过新颖的方法，其中5-芳基羰基-4-的S-烷基化，以高收率合成了各种1-芳基羰基-3-[（未）取代的甲硫基]噻吩并[3,4-b]吲哚嗪-9-羧酸乙酯。将乙氧基羰基甲基-3-（1-吡啶基）噻吩-2-硫醇盐与烷基或苄基卤化物，在碱存在下将所得吡啶鎓盐进行1,5-偶极环化，并进行芳构化。在一些3-（苄硫基）硫代[3,4-b]吲哚并嗪-9-羧酸盐的X射线分析中，发现了与环外硫键有关的薄纱和两个反构象体。有趣的是，所有3-（苄硫基）噻吩并[3,4-b]吲哚并嗪衍生物均显示出显着的高场频移（δ直至0。

  DOI：

  10.1248/cpb.51.75

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.
• Syntheses of Some 1-(α-Hydroxybenzyl)thieno[3,4-b]indolizine Derivatives and Their Unexpected Condensation Reactions
  作者：Akikazu Kakehi、Hiroyuki Suga、Shin Hatayama、Daisuke Kubo

  DOI：10.3987/com-05-10406

  日期：——

  Some ethyl 3-(benzyl or methylthio)-1-(alpha-hydroxybenzyl)- thieno[3,4-b]indolizine-9-carboxylates were prepared by the reduction of the corresponding 1-benzoyl derivatives with sodium borohydride. These compounds were considerably unstable and their treatment with acetic acid afforded the unexpected condensation products.
• Preparation of New Nitrogen-Bridged Heterocycles. 53. Syntheses of 3-(Benzylthio)thieno[3,4-b]indolizine Derivatives and Their Intramolecular Arene-Arene Interactions.
  作者：Akikazu Kakehi、Suketaka Ito、Hiroyuki Suga、Takeyuki Miwa、Takashi Mori、Tsuneo Fujii、Nobuaki Tanaka、Tomoshige Kobayashi

  DOI：10.1248/cpb.51.75

  日期：——

  3-(benzylthio)thieno[3,4-b]indolizine derivatives showed significant high-field shifts (delta up to 0.3 ppm) for the 5- and 6-proton signals compared with those of the 3-methylthio derivatives in the (1)H-NMR spectra and exhibited a definite absorption band near 425 nm in their UV spectra, indicating an intramolecular arene-arene interaction between the thieno[3,4-b]indolizine and the phenyl ring.

  通过新颖的方法，其中5-芳基羰基-4-的S-烷基化，以高收率合成了各种1-芳基羰基-3-[（未）取代的甲硫基]噻吩并[3,4-b]吲哚嗪-9-羧酸乙酯。将乙氧基羰基甲基-3-（1-吡啶基）噻吩-2-硫醇盐与烷基或苄基卤化物，在碱存在下将所得吡啶鎓盐进行1,5-偶极环化，并进行芳构化。在一些3-（苄硫基）硫代[3,4-b]吲哚并嗪-9-羧酸盐的X射线分析中，发现了与环外硫键有关的薄纱和两个反构象体。有趣的是，所有3-（苄硫基）噻吩并[3,4-b]吲哚并嗪衍生物均显示出显着的高场频移（δ直至0。
• Preparation of new nitrogen-bridged heterocycles. 69. Synthesis and Reaction of 1-(α-Hydroxybenzyl)thieno [3,4-b] indolizine Derivatives
  作者：Akikazu Kakehi、Hiroyuki Suga、Yukihisa Okumura、Kennosuke Itoh、Shin Hatayama、Daisuke Kubo、Kouji Kobayashi

  DOI：10.1515/hc.2010.16.1.53

  日期：2010.1

  The title compounds, l-(a-hydroxybenzyl)thieno[3,4-o]indolizine derivatives, were obtained in good yields by the reduction of the corresponding l-benzoylthieno[3,4-6]indolizines with sodium borohydride in refluxing ethanol. These compounds were considerably unstable and decomposed gradually even at room temperature, but, on exposure to acetic acid, unexpected condensation took place to afford a,]i

  通过在回流乙醇中用硼氢化钠还原相应的 l-苯甲酰基噻吩并 [3,4-6] 吲哚腙，以良好的收率获得标题化合物，即 l-(α-羟基苄基) 噻吩并 [3,4-o] 吲哚嗪衍生物. 这些化合物相当不稳定，即使在室温下也逐渐分解，但是，在暴露于乙酸时，会发生意想不到的缩合反应，在低至中等浓度下得到 a,]indolizin-l-yl) 甲苯