1-Methyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile | 95546-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-Methyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile
• 英文别名: 1-methyl-3-sulfanylidene-5,6,7,8-tetrahydro-2H-isoquinoline-4-carbonitrile
• CAS: 95546-96-6
• 化学式: C₁₁H₁₂N₂S
• mdl: MFCD01106275
• 分子量: 204.296
• InChiKey: NBBIVWBHKOGCDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Methyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile 以97%的产率得到
  参考文献：
  名称：

  SHARANIN, YU. A.;SHESTOPALOV, A. M.;PROMONENKOV, V. K.;RODINOVSKAYA, L. A+, ZH. ORGAN. XIMII, 1984, 20, N 11, 2432-2441

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Morpholino-2-acetyl-cyclohexen-(1) 在 sodium ethanolate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 1-Methyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile
  参考文献：
  名称：

  Synthesis of the functionally 4-substituted 1-methyl-3-thioxo-2,3,5,6,7,8-hexahydroisoquinolines by SNVin reaction of 2-acetyl-1-(N-morpholinyl)cyclohexene with malonothio(dithio)amides

  摘要：

  4-Carbamoyl(thiocarbamoyl)-3-thioxo-2,3,5,6,7,8-hexahydroisoquinolines were synthesized by the S(N)Vin reaction of 2-acetyl-1-(N-morpholinyl)acetylcyclohexene with malonothio(dithio)amides. The cyclocondensation direction was confirmed with the X-ray diffraction analysis of 1-methyl-3-methylthio-5,6,7,8-tetrahydroisoquinoline-4-carboxamide.

  DOI：

  10.1134/s1070363212020156

文献信息

• Synthesis of condensed heteroaromatics: novel synthesis of aminoquinolizinone derivatives as anti-HIV agents
  作者：Fatima Al-Omran、Abdel-Zaher A Elassar、Adel A El-Khair

  DOI：10.1016/s0040-4020(01)01039-0

  日期：2001.12

  New routes for the synthesis of aminoquinolizinone derivatives with interesting biological activities are reported. Reactions enaminones 2 and 9 with malononitrile affords aminoquinolizinone derivatives 7a and 7b. Fusion of acetylcyclohexanone (1) with DMF DMA and ethyl cyanoacetate affords only product 11. Treatment of the latter product with malononitrile affords the aminoquinolizinone derivative

  报道了合成具有有趣生物活性的氨基喹嗪酮衍生物的新途径。烯胺2和9与丙二腈的反应得到氨基喹嗪酮衍生物7a和7b。乙酰基环己酮（1）与DMF DMA和氰基乙酸乙酯的融合仅提供产物11。用丙二腈处理后一产物得到氨基喹啉酮衍生物15。查耳酮17与丙二腈的反应提供了产物22。（1）与亚芳基丙二腈23a，b的缩合分别提供化合物28a，b。通过元素分析和1 H NMR光谱，以及在某些情况下通过13 C NMR研究，阐明了新合成化合物的结构。
• On the regioselectivity of the reaction of cyanothioacetamide with 2-acetylcyclo-hexanone, 2-acetylcyclopentanone, and 2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes
  作者：V. V. Dotsenko、S. G. Krivokolysko、V. V. Polovinko、V. P. Litvinov

  DOI：10.1007/s10593-012-0991-5

  日期：2012.5

  It has been established that the interaction of cyanothioacetamide with 2-acetylcyclohexanone, 2-acetylcyclopentanone, or their enamines (2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes) contrary to the literature data have a non-regiospecific character and leads to the formation of mixtures of 3-cyano-4-methyl-5,6-tri(tetra)methylenepyridine-2(1 H)-thiones and 3-cyano-6-methyl-4,5-tri(tetra)methylene-pyridine-2(1 H)-thiones with a predominance of the latter.
• Sharanin, Yu. A.; Shestopalov, A. M.; Promonenkov, V. K., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 2216 - 2224
  作者：Sharanin, Yu. A.、Shestopalov, A. M.、Promonenkov, V. K.、Rodinovskaya, L. A.

  DOI：——

  日期：——
• Synthesis and alkylation of 1-substituted 3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitriles
  作者：I. V. Dyachenko、M. V. Vovk

  DOI：10.1134/s1070428012120081

  日期：2012.12

  The condensation of cyclohexylidene(cyano)thioacetamides with aldehydes or of 2-acyl-1-(morpholin-4-yl)cycloalkenes with dithiomalonamide gave 1-alkyl(aryl)-3-thioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitriles. Reactions of the latter with various alkylating agents selectively produced the corresponding isoquinolin-3-yl sulfides or products of their subsequent Thorpe cyclization, thieno[2,3-c]isoquinolines.
• Synthesis and evaluation of pyrido-thieno-pyrimidines as potent and selective Cdc7 kinase inhibitors
  作者：Chunlin Zhao、Christian Tovar、Xuefeng Yin、Qui Xu、Ivan T. Todorov、Lyubomir T. Vassilev、Li Chen

  DOI：10.1016/j.bmcl.2008.11.093

  日期：2009.1

  Cdc7 kinase plays a critical role in the regulation of DNA replication in eukaryotic cells and has been proposed as a target for cancer therapy. We have identified a class of Cdc7/Dbf4 inhibitors with a pyrido-thieno-pyrimidine core structure. Synthesis of a focused pyrido-thieno-pyrimidine library yielded potent and selective Cdc7 inhibitors with antiproliferative activity against cancer cells in vitro. Their synthesis and SAR data are presented herein. (C) 2008 Elsevier Ltd. All rights reserved.