Diethyl 2-(3-ethoxy-3-oxopropyl)sulfanyl-6,8-dimethylindolizine-1,3-dicarboxylate | 129169-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: Diethyl 2-(3-ethoxy-3-oxopropyl)sulfanyl-6,8-dimethylindolizine-1,3-dicarboxylate
• CAS: 129169-99-9
• 化学式: C₂₁H₂₇NO₆S
• 分子量: 421.514
• InChiKey: MGXJWGSYVQOKKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Diethyl 2-(3-ethoxy-3-oxopropyl)sulfanyl-6,8-dimethylindolizine-1,3-dicarboxylate 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 2-Acetyl-3-hydroxy-4,6-dimethyl-1-thia-7a-aza-cyclopenta[a]indene-8-carboxylic acid ethyl ester
  参考文献：
  名称：

  Preparation of new nitrogen-bridged heterocycles. XXII. A new approach to the syntheses of thienoindolizine derivatives.

  摘要：

  在 N，N-二甲基甲酰胺中用叔丁醇钾对 2-[(2-取代乙基)硫]-3-吲嗪甲酸乙酯（1a-f 和 5a-f）进行脱保护，并用各种烷基化剂如氯丙酮（3a）对生成的 2-吲嗪硫醇钾进行烷基化、苯甲酰基溴化物（3b-d）和硝基苄基溴化物（3e，f）进行烷基化，可顺利得到相应的 S-羽氨化吲哚利嗪衍生物（4a-r 和 6a-r），产率相当高。另一方面，3-乙酰基-2-[（2-取代乙基）硫代]吲嗪（7a-f）的类似反应提供了 3-甲基噻吩并[2, 3-b]吲嗪衍生物（8a-o），这些衍生物是最初生成的 S-烷基化吲嗪在此处采用的反应条件下进一步分子内环化形成的。上述官能化的吲嗪类化合物（4a-r 和 6a-r）还可以在各种碱性条件下转化为相应的噻吩并[3，2-α]-（10a-r、14a-d 和 15a，b）和噻吩并[2，3-b]吲嗪衍生物（11a-h 和 12a-d）。

  DOI：

  10.1248/cpb.38.1527
• 作为产物：
  描述：

  3,5-dimethylpyridinium 1-ethoxycarbonyl-2-[(2-ethoxycarbonylethyl)thio]-2-thioxoethylide 、 溴乙酸乙酯 生成 Diethyl 2-(3-ethoxy-3-oxopropyl)sulfanyl-6,8-dimethylindolizine-1,3-dicarboxylate
  参考文献：
  名称：

  KAKEHI, AKIKAZU;ITO, SUKETAKA;YAMADA, NAOAKI;YAMAGUCHI, KIMINOBU, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 829-834

  摘要：

  DOI：

文献信息

• Preparation of New Nitrogen-Bridged Heterocycles. 51. Syntheses and Structures of Compounds Having Two Indolizine Nuclei in a Molecule.
  作者：Akikazu KAKEHI、Suketaka ITO、Hiroyuki SUGA、Shinji SAKURAI、Tomoshige KOBAYASHI

  DOI：10.1248/cpb.49.1401

  日期：——

  New compounds having two indolizine nuclei in a molecule were prepared in low to moderate yields from the reactions of potassium 2-indolizinethiolates with 1,ω-dihalides such as 1,2-diiodoethane, 1,3-dibromopropane, 1,4-dibromobutane, α,α'-dichloro-o-xylene, and α,α'-dichloro-p-xylene. Most of the products had the conformation in which the two indolizine rings in the molecule are as remote as possible, but only 1,2-bis[[(2-indolizinyl)thio]methyl]benzene derivatives, prepared from potassium 2-indolizinethiolates and α,α'-dichloro-o-xylene, showed a weak attractive interaction between the two indolizine nuclei in the X-ray analysis and the nuclear Overhauser and exchange spectroscopy (NOESY) spectrum.

  通过 2-中氮茚硫醇钾与 1,ω-二卤化物如 1,2-二碘乙烷、1,3-二溴丙烷、1,4-二溴丁烷、 α,α'-二氯邻二甲苯和α,α'-二氯对二甲苯。大多数产物具有分子中两个中氮茚环尽可能远离的构象，但只有1,2-双[[(2-中氮茚基)硫代]甲基]苯衍生物，由2-中氮茚硫醇钾和α,α'-二氯邻二甲苯，在 X 射线分析以及核奥沃豪瑟和交换光谱 (NOESY) 中显示出两个中氮茚核之间存在弱吸引力相互作用 光谱。
• Peparation of New Nitrogen-bridged Heterocycles. 21. A Facile Synthesis of 2-Indolizinethiols Using New Protecting Groups
  作者：Akikazu Kakehi、Suketaka Ito、Naoaki Yamada、Kiminobu Yamaguchi

  DOI：10.1246/bcsj.63.829

  日期：1990.3

  Some indolizine derivatives having (2-cyanoethyl)thio or (2-ethoxycarbonylethyl)thio group at the 2-position were prepared in moderate to good yields starting from the corresponding pyridinium 1-(thiocarbonyl)methylides. The treatment of these indolizines with a strong base such as potassium t-butoxide in N,N-dimethylformamide (DMF) gave smoothly title compounds, 2-indolizinethiols, with the elimination

  从相应的吡啶鎓1-（硫代羰基）甲基化物开始，以中等至良好的产率制备了一些在2-位具有（2-氰基乙基）硫基或（2-乙氧基羰基乙基）硫基的吲哚嗪衍生物。用强碱如叔丁醇钾在 N,N-二甲基甲酰胺 (DMF) 中处理这些吲哚腙，可顺利得到标题化合物 2-吲哚腙硫醇，同时去除丙烯腈或丙烯酸乙酯。
• Preparation of New Nitrogen-Bridged Heterocycles. 27. First Syntheses of 1,3-Thiazino[6,5-<i>b</i>]indolizine Derivatives
  作者：Akikazu Kakehi、Suketaka Ito、Tosio Sakurai、Kunio Urushido、Hidetoshi Isawa、Manabu Enomoto

  DOI：10.1246/bcsj.64.3289

  日期：1991.11

  The reactions of 2-[mercapto(methylthio)methylene]-2(3H)-indolizinones with alkyl isothiocyanates in the presence of potassium t-butoxide in N,N-dimethylformamide afforded new heterocycles, 3-alkyl-2H-1,3-oxazino[6,5-b]indolizine-2,4(3H)-dithione derivatives, in moderate yields. On the other hand, their reactions with phenyl isothiocyanate did not afford the corresponding 2H-1,3-oxazino[6,5-b]indolizine-2

  2-[巯基(甲硫基)亚甲基]-2(3H)-吲哚嗪酮与异硫氰酸烷基酯在叔丁醇钾存在下在 N,N-二甲基甲酰胺中反应得到新的杂环，3-烷基-2H-1,3- oxazino[6,5-b]indolizine-2,4(3H)-dithione 衍生物，产率适中。另一方面，它们与异硫氰酸苯酯的反应没有得到相应的 2H-1,3-oxazino[6,5-b]indolizine-2,4(3H)-dithiones，尽管 2-[mercapto(methylthio )methylene]-1-methyl-2(3H)-indolizinone 与苯基异硫氰酸酯得到 10-methyl-3-phenyl-2-phenylimino-2,3-dihydro-4H-1,3-oxazino[6,5-b] indolizine-4-thione 的产率非常低 (10%)。这些 2H-1,3-oxazino[6,5-b]indolizine-2
• Preparation of New Nitrogen-bridged Heterocycles. 47. Reactions of 2-Indolizinethiolates with Acetylenic Compounds
  作者：Akikazu Kakehi、Suketaka Ito、Hiroyuki Suga、Hiroyuki Takahashi、Kazuhiro Dobashi

  DOI：10.3987/com-99-s12

  日期：——

  The reactions of potassium 2-indolizinethiolates having an ester group at the 3-position with some electron deficient acetylenic compounds were investigated. Their Michael additions or Michael addition-cyclizations proceeded with the elimination of an ester group to provide the corresponding 2-vinylthioindolizine and 4H-thiino[2,3-b]indolizin-4-one derivatives.
• First Formation of Thiepino[2,3-b]- and Thiepino[3,2-a]indolizine Derivatives
  作者：Akikazu Kakehi、Hidetoshi Isawa、Hiroyuki Suga

  DOI：10.3987/com-08-11536

  日期：——

  The reactions of potassium 1,3-bis(ethoxycarbonyl)indolizine-2-thiolates with ethyl 4-bromocrotonate afforded the corresponding indolizine derivatives having (E)-(3-ethoxycarbonyl-2-propenyl)thio, (E)- and (Z)-(3-ethoxycarbonyl-1-propenyl)thio group at the 2-position. The alkaline treatment of these S-alkylated indolizines gave the title compounds in good yields.