1-methylthio-3,4-dihydropyridino<2.1-a>isoindol-2,6-dione | 128365-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1-methylthio-3,4-dihydropyridino<2.1-a>isoindol-2,6-dione
• 英文别名: 1-methylthio-3,4-dihydropyrido<2.1-a>isoindole-2,5-dione；1-methylthio-3,4-dihydropyrido[2,1-a]isoindole-2,6-dione；Pyrido[2,1-a]isoindole-2,6-dione, 3,4-dihydro-1-(methylthio)-；1-methylsulfanyl-3,4-dihydropyrido[1,2-b]isoindole-2,6-dione
• CAS: 128365-79-7
• 化学式: C₁₃H₁₁NO₂S
• 分子量: 245.302
• InChiKey: DACCWKVNVWJQCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-methylthio-3,4-dihydropyridino<2.1-a>isoindol-2,6-dione 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以70%的产率得到吡啶并[2,1-a]异吲哚-6(2H)-酮,3,4-二氢-2-羟基-1-(甲硫基)-
  参考文献：
  名称：

  摘要：

  The reaction of 1-methylthio-3,4-dihydropyrido[2,1-a]isoindole-2,6-dione (2) with NaBH4 led to reduction of the keto group to the hydroxy group. The reaction with the use of LiAlH4 resulted in complete reduction of the carboximide group, reduction of the keto group to the hydroxy function, and reduction of the double bond accompanied by desulfurization. The reaction of indolizidinedione 2 with Zn afforded a reductive desulfurization product. The reactions of 2 with hydrazine hydrate, hydroxylamine, and formamide proceeded according to a mechanism typical of the keto group to give hydrazone, oxime, and the formyl derivative, respectively. Oxidation of the thiomethyl group of the starting compound with (BuOOH)-O-t gave rise to sulfone or sulfoxide depending on the amount of the oxidizing agent used.

  DOI：

  10.1023/a:1019626005246
• 作为产物：
  描述：

  2-(4-溴-3-氧代丁基)-1H-异吲哚-1,3(2H)-二酮 以 甲苯 为溶剂， 生成 1-methylthio-3,4-dihydropyridino<2.1-a>isoindol-2,6-dione
  参考文献：
  名称：

  Β-丙氨酸新合成吲哚嗪二酮

  摘要：

  DOI：

  10.1007/bf00473877

文献信息

• Sulfonium ylides
  作者：F. Z. Galin、S. N. Lakeev、G. A. Tolstikov

  DOI：10.1007/bf01433752

  日期：1996.1

  transformations of phthalimido-substituted keto-stabilized sulfonium ylides, including optically active ylides, were studied. The thermolysis of sulfonium ylides obtained from α- and β-amino acids leads to methylthio-substituted pyrrolizidine- and indolizidinediones. Racemization of optically active ylides does not occur. Sulfonium ylides with longer carbon chains do not undergo intramolecular cyclization

  研究了邻苯二甲酰亚胺取代的酮基稳定的锍叶立德（包括光学活性叶立德）的热转化。从α-和β-氨基酸获得的锍叶立德的热解导致甲硫基取代的吡咯里西啶和吲哚里西二酮。不会发生旋光叶立德的外消旋化。具有较长碳链的锍叶立德不发生分子内环化。
• ——
  作者：S. N. Lakeev、I. Z. Mullagalin、I. O. Maidanova、F. Z. Galin、G. A. Tolstikov

  DOI：10.1023/a:1015054907007

  日期：——

  A modified method for the synthesis of derivatives of pyrrolizinedione and indolizinedione was proposed. The method is based on the intramolecular cyclization of keto-stabilized sulfur ylides generated in situ from diazo ketones and Me2S in the presence of Rh-2(OAc)(4).
• GALIN, F. Z.;LAKEEV, S. N.;TOLSTIKOV, G. A., XIMIYA GETEROTSIKL. SOED.,(1989) N2, S. 1693-1694
  作者：GALIN, F. Z.、LAKEEV, S. N.、TOLSTIKOV, G. A.

  DOI：——

  日期：——

表征谱图