trans-(7S,8S)-1,4-dithiaspiro[4.4]nonane-7,8-dicarboxylic acid bis(methyl ester) | 192385-75-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: trans-(7S,8S)-1,4-dithiaspiro[4.4]nonane-7,8-dicarboxylic acid bis(methyl ester)
• 英文别名: dimethyl (7S,8S)-1,4-dithiaspiro[4.4]nonane-7,8-dicarboxylate
• CAS: 192385-75-4
• 化学式: C₁₁H₁₆O₄S₂
• 分子量: 276.378
• InChiKey: DDGSVODYDWXKIB-YUMQZZPRSA-N

物化性质

• 沸点：
  394.9±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trans-(7S,8S)-1,4-dithiaspiro[4.4]nonane-7,8-dicarboxylic acid bis(methyl ester) 在 sodium hydroxide 、 二苯基膦叠氮化物 、 镍 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 25.0h， 生成 (1S,2s)-boc-2-氨基环戊烷羧酸
  参考文献：
  名称：

  Synthesis of enantiomerically pure cis and trans 2-aminocyclopentanecarboxylic acids. Use of proline replacements in potential HIV-protease inhibitors

  摘要：

  The synthesis of the four diastereomeric 2-aminocyclopentanecarboxylic acids, their use as replacements for proline in potential HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere and the evaluation of the biological activity of these is described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00482-1
• 作为产物：
  描述：

  trans dimethyl cyclopentanone 3,4-dicarboxylate 、 1,2-乙二硫醇 在 Cu(OTf)2-SiO₂ 作用下， 反应 24.0h， 以93%的产率得到trans-(7S,8S)-1,4-dithiaspiro[4.4]nonane-7,8-dicarboxylic acid bis(methyl ester)
  参考文献：
  名称：

  Solvent Free Thioacetalization of Carbonyl Compounds Catalyzed by Cu(OTf)₂-SiO₂

  摘要：

  醛和酮在无溶剂条件下，使用1,2-乙二硫醇，在催化量的Cu(OTf)2-SiO2存在下，进行了硫代乙酰化反应，产率极佳。

  DOI：

  10.1055/s-1999-2635

文献信息

• New Proline Mimetics:  Synthesis of Thrombin Inhibitors Incorporating Cyclopentane- and Cyclopentenedicarboxylic Acid Templates in the P2 Position. Binding Conformation Investigated by X-ray Crystallography
  作者：Daniel Nöteberg、Jonas Brånalt、Ingemar Kvarnström、Marcel Linschoten、Djordje Musil、Jan-Erik Nyström、Guido Zuccarello、Bertil Samuelsson

  DOI：10.1021/jm990557t

  日期：2000.5.1

  With the aim to prepare nonpeptidic thrombin inhibitors, the amino acids of the thrombin-inhibiting tripeptide chain D-Phe-Pro-Arg were replaced with isosteres. Arg was replaced with the more rigid P1 truncated p-amidinobenzylamine (Pab), Pro with either cyclopentane-1,2-dicarboxylic acid or cyclopentene-1,5-dicarboxylic acid, and D-Phe with a series of readily available lipophilic amines. One of the most potent compounds (25, pIC(50) = 6.01) in these series was cocrystallized with thrombin where the X-ray crystal structure provide insight to the structure-activity relationship (SAR).
• Solvent Free Thioacetalization of Carbonyl Compounds Catalyzed by Cu(OTf)₂-SiO₂
  作者：R. Vijaya Anand、P. Saravanan、Vinod K. Singh

  DOI：10.1055/s-1999-2635

  日期：1999.4

  Aldehydes and ketones were thioacetalyzed using 1,2-ethanedithiol in the presence of a catalytic amount of Cu(OTf)2-SiO2 under solvent free conditions in excellent yields.

  醛和酮在无溶剂条件下，使用1,2-乙二硫醇，在催化量的Cu(OTf)2-SiO2存在下，进行了硫代乙酰化反应，产率极佳。
• Synthesis of enantiomerically pure cis and trans 2-aminocyclopentanecarboxylic acids. Use of proline replacements in potential HIV-protease inhibitors
  作者：Daniel Nöteberg、Jonas Brånalt、Ingemar Kvarnström、Björn Classon、Bertil Samuelsson、Ulrika Nillroth、U.Helena Danielson、Anders Karlén、Anders Hallberg

  DOI：10.1016/s0040-4020(97)00482-1

  日期：1997.6

  The synthesis of the four diastereomeric 2-aminocyclopentanecarboxylic acids, their use as replacements for proline in potential HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere and the evaluation of the biological activity of these is described. (C) 1997 Elsevier Science Ltd.