ethyl 3,3-bis(methylthio)-2-isopropylacrylate | 132767-06-7

• 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: ethyl 3,3-bis(methylthio)-2-isopropylacrylate
• 英文别名: ethyl 3,3-(dimethylthio)-2-isopropylacrylate；Ethyl 2-[bis(methylsulfanyl)methylidene]-3-methylbutanoate
• CAS: 132767-06-7
• 化学式: C₁₀H₁₈O₂S₂
• 分子量: 234.384
• InChiKey: INQNSNVBVGHDNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  108-112 °C(Press: 4 Torr)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3,3-bis(methylthio)-2-isopropylacrylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以82%的产率得到3,3-(dimethylthio)-2-isopropylacrylic acid
  参考文献：
  名称：

  1,5-二烷基-6-（芳基硒烯）尿嘧啶和-2-硫尿嘧啶的合成及抗HIV-1活性†

  摘要：

  已经合成了1，5-二烷基-6-（芳基硒烯基）尿嘧啶10a-h和-2-硫尿嘧啶10i-p作为潜在的抗HIV-1试剂。的环化Ñ -烷基- N” - [3,3-二（甲硫基）-2- alkylacryloyl]脲图6a-d和-thioureas 6E-H在乙酸或者含有甲磺酸催化量在80℃或含有1室温下当量的甲磺酸得到84,96％产率的1,5-二烷基-6-（甲硫基）尿嘧啶7a-d和1,5-二烷基-5,6-二氢-6,6-二甲硫基-2-硫尿嘧啶11a-d的产率分别为88-99％。7a-d和11a-d的氧化用苯中的3-氯过氧苯甲酸或高碘酸钠水溶液的甲醇溶液制得1,5-二烷基-6-（甲基磺酰基）尿嘧啶8a-d，产率为88-98 ％，而1,5-二烷基-6-（甲基磺酰基）- 2-硫尿嘧啶12a-d的收率分别为57-73％，随后将其用芳基硒醇9a-b在氢氧化钠乙醇溶液中处理，以6099％的收率得到10a-p。这些化合物中，6-[[（3

  DOI：

  10.1002/jhet.5570330356
• 作为产物：
  描述：

  二硫化碳 、 异戊酸乙酯 、 碘甲烷 在 lithium diisopropyl amide 作用下， 生成 ethyl 3,3-bis(methylthio)-2-isopropylacrylate
  参考文献：
  名称：

  Synthesis and Anti-HIV-1 Activity of a Series of 1-Alkoxy-5-alkyl-6-(arylthio)uracils

  摘要：

  A series of 1-alkoxy-5-alkyl-6-(arylthio)uracils was synthesized and tested for their ability to inhibit HIV-1 replication. Treatment of 2-alkyl-3,3-bis(methylthio)acryloyl chlorides (5a-e) with AgOCN in benzene followed by reaction of the resulting isocyanates 6a-e with an appropriate alkoxyamine gave N-alkoxy-N'-((2-alkyl-3,3-bis(methylthio (10a-z) in good to excellent yields. Cyclization of 10a-z in AcOH containing st catalytic amount of p-TsOH produced 1-alkaxy-5-alkyl-6-(methylthio)uracils (11a-z). Oxidation of 11a-z with 3-chloroperoxybenzoic acid in CH2Cl2 resulted in high yields of 1-alkoxy-5-alkyl-6-(methylsulfonyl)uracils (12a-x and 12z) and 1-(benzyloxy)-6-(methylsulfinyl)thymine (12y), which were subsequently reacted with an appropriate arenethiol in ethanolic NaOH solution to afford 1-alkoxy-5-alkyl-6-(arylthio)uracils (14-49). Substitution at the 3- and 5-positions of the C-6-(phenylthio) ring by two methyl groups significantly increased its original anti-HIV-l activity (EC50: 6-((3,5-dimethylphenyl)thio)-5-isopropyl-1-propoxyuracil (18), 0.064 mu M; 6-((3,5-dimethylphenyl)thio)-1-(3-hydroxypropoxy)-5-isopropyluracil (23), 0.19 mu M). Among the various alkoxy substituents at the N-1, the propoxy group was the most beneficial for improving the anti-HIV-1 activity. The 1-propoxy derivative 18 proved to be the most potent inhibitor of HIV-1 replication, followed by the 1-(3-hydroxypropoxy) derivative 23. Introduction of an isopropyl group at C-5 of the uracil base also remarkably enhanced the activity. When compound 18 was incubated with a rat liver homogenate preparation, no metabolite was observed, thus confirming the metabolic stability of the N-O bond in these 1-alkoxyuracils.

  DOI：

  10.1021/jm9607921

文献信息

• Synthesis and anti-HIV-1 activity of 1,5-dialkyl-6-(arylselenenyl)uracils and -2-thiouracils
  作者：Dae-Kee Kim、Hun-Taek Kim、Jinsoo Lim、Jongsik Gam、Young-Woo Kim、Key H. Kim、Young Oh Shin

  DOI：10.1002/jhet.5570330356

  日期：1996.5

  6e-h in acetic acid either containing a catalytic amount of methanesulfonic acid at 80°or containing 1 equivalent of methanesulfonic acid at room temperature afforded 1,5-dialkyl-6-(methylthio)uracils 7a-d in 84–96% yields and 1,5-dialkyl-5,6-dihydro-6,6-di(methylthio)-2-thiouracils 11a-d in 88–99% yields, respectively. Oxidation of 7a-d and 11a-d with either 3-chloroperoxybenzoic acid in benzene or aqueous

  已经合成了1，5-二烷基-6-（芳基硒烯基）尿嘧啶10a-h和-2-硫尿嘧啶10i-p作为潜在的抗HIV-1试剂。的环化Ñ -烷基- N” - [3,3-二（甲硫基）-2- alkylacryloyl]脲图6a-d和-thioureas 6E-H在乙酸或者含有甲磺酸催化量在80℃或含有1室温下当量的甲磺酸得到84,96％产率的1,5-二烷基-6-（甲硫基）尿嘧啶7a-d和1,5-二烷基-5,6-二氢-6,6-二甲硫基-2-硫尿嘧啶11a-d的产率分别为88-99％。7a-d和11a-d的氧化用苯中的3-氯过氧苯甲酸或高碘酸钠水溶液的甲醇溶液制得1,5-二烷基-6-（甲基磺酰基）尿嘧啶8a-d，产率为88-98 ％，而1,5-二烷基-6-（甲基磺酰基）- 2-硫尿嘧啶12a-d的收率分别为57-73％，随后将其用芳基硒醇9a-b在氢氧化钠乙醇溶液中处理，以6099％的收率得到10a-p。这些化合物中，6-[[（3
• Pyrimidine acyclonucleoside derivatives
  申请人：Sunkyong Industries Co., Inc.

  公开号：US05889013A1

  公开（公告）日：1999-03-30

  The present invention relates to novel pyrimidine acyclonucleoside derivatives represented by the following general formula (I), antiviral agents containing the derivatives as the active ingredients and processes of preparation thereof. ##STR1## wherein R.sup.1 is ethyl or isopropyl; R.sup.2 is (3,5 dimethylphenyl)selenenyl; R.sup.3 is phenyl or methyl; X is oxygen; and Y is oxygen.

  本发明涉及以下一般式（I）所代表的新型嘧啶缺环核苷衍生物，包含该衍生物作为活性成分的抗病毒剂以及其制备方法。其中，R.sup.1为乙基或异丙基；R.sup.2为（3,5-二甲基苯基）硒基；R.sup.3为苯基或甲基；X为氧；Y为氧。
• Samarium diiodide-promoted reductive cleavage of carbon-sulfur bonds: a novel stereoselective generation of functionalized vinylsamarium species and synthesis of .beta.-thiobutenolides
  作者：Makoto Hojo、Hajime Harada、Junji Yoshizawa、Akira Hosomi

  DOI：10.1021/jo00076a004

  日期：1993.11

  (Alkoxycarbonyl)ketene dithioacetals are cleanly reduced by SmI2 to provide a new and efficient method for the stereoselective generation of the corresponding novel highly functionalized vinylsamarium species which react with a proton, allyl bromide, and aldehydes to give the corresponding reduction products, allylation products, and beta-thiobutenolides, respectively.

  （烷氧基羰基）酮二硫代乙酸酯在SmI2的作用下被干净地还原，提供了一種新的、高效的立體選擇性方法，生成相應的高官能化烯基釸化合物。這些烯基釸化合物分別與質子、烯丙基溴和醛反應，生成相應的還原产物、烯丙基化产物和β-硫丁内酯。
• PYRIMIDINE ACYCLONUCLEOSIDE DERIVATIVES
  申请人：SUNKYONG INDUSTRIES CO., LTD.

  公开号：EP0748316B1

  公开（公告）日：2002-05-08
• US5889013A
  申请人：——

  公开号：US5889013A

  公开（公告）日：1999-03-30