(E)-3-[(4S,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl]-1-piperidin-1-ylprop-2-en-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (E)-3-[(4S,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl]-1-piperidin-1-ylprop-2-en-1-one
• 化学式: C₁₀H₁₀NO₂Pol
• InChiKey: DOXPOYZMVYURGU-OEPMCUGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-[(4S,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl]-1-piperidin-1-ylprop-2-en-1-one 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以93%的产率得到(4S,5R)-2E-4,5-dihydroxy-1-(piperidin-1-yl)dec-2-en-1-one
  参考文献：
  名称：

  辣椒根新酰胺生物碱的首次立体选择性全合成和抗癌活性

  摘要：

  的新的天然酰胺生物碱第一立体选择性全合成1 - 3已经从可商购的起始材料来实现的。Wittig烯烃化，Sharpless不对称二羟基化，环氧化，2,3-环氧醇的反式区域选择性开放，Horner-Wadsworth-Emmons（HWE）烯烃化和酰胺偶联是关键步骤。酰胺生物碱1 - 3用于抗结肠癌的人癌细胞系首次其抗癌活性（HT-29），乳腺癌（MCF-7）和肺（A-549）进行评价。

  DOI：

  10.1016/j.bmcl.2009.08.056
• 作为产物：
  描述：

  2-fluoro-N-(4-hexylphenyl)-5-nitrobenzamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 (E)-3-[(4S,5R)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl]-1-piperidin-1-ylprop-2-en-1-one
  参考文献：
  名称：

  Discovery of benzimidazole-diamide finger loop (Thumb Pocket I) allosteric inhibitors of HCV NS5B polymerase: Implementing parallel synthesis for rapid linker optimization

  摘要：

  Previously described SAR of benzimidazole-based non-nucleoside finger loop (Thumb Pocket I) inhibitors of HCV NS5B polymerase was expanded. Prospecting studies using parallel synthesis techniques allowed the rapid identification of novel cinnamic acid right-hand sides that provide renewed opportunities for further optimization of these inhibitors. Novel diamide derivatives such as 44 exhibited comparable potency (enzymatic and cell-based HCV replicon) as previously described tryptophan-based inhibitors but physicochemical properties (e. g., aqueous solubility and lipophilicity) have been improved, resulting in molecules with reduced off-target liabilities (CYP inhibition) and increased metabolic stability. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.136

文献信息

• Discovery of benzimidazole-diamide finger loop (Thumb Pocket I) allosteric inhibitors of HCV NS5B polymerase: Implementing parallel synthesis for rapid linker optimization
  作者：Sylvie Goulet、Marc-André Poupart、James Gillard、Martin Poirier、George Kukolj、Pierre L. Beaulieu

  DOI：10.1016/j.bmcl.2009.10.136

  日期：2010.1

  Previously described SAR of benzimidazole-based non-nucleoside finger loop (Thumb Pocket I) inhibitors of HCV NS5B polymerase was expanded. Prospecting studies using parallel synthesis techniques allowed the rapid identification of novel cinnamic acid right-hand sides that provide renewed opportunities for further optimization of these inhibitors. Novel diamide derivatives such as 44 exhibited comparable potency (enzymatic and cell-based HCV replicon) as previously described tryptophan-based inhibitors but physicochemical properties (e. g., aqueous solubility and lipophilicity) have been improved, resulting in molecules with reduced off-target liabilities (CYP inhibition) and increased metabolic stability. (C) 2009 Elsevier Ltd. All rights reserved.
• First stereoselective total synthesis and anticancer activity of new amide alkaloids of roots of pepper
  作者：Ch. Srinivas、Ch.N.S. Sai Pavan Kumar、B. China Raju、V. Jayathirtha Rao、V.G.M. Naidu、S. Ramakrishna、Prakash V. Diwan

  DOI：10.1016/j.bmcl.2009.08.056

  日期：2009.10

  The first stereoselective total synthesis of new natural amide alkaloids 1–3 have been achieved from commercially available starting materials. Wittig olefination, Sharpless asymmetric dihydroxylation, epoxidation, a trans regioselective opening of 2,3-epoxy alcohol, Horner–Wadsworth–Emmons (HWE) olefination and amide coupling are the key steps. The amide alkaloids 1–3 are evaluated for their anticancer

  的新的天然酰胺生物碱第一立体选择性全合成1 - 3已经从可商购的起始材料来实现的。Wittig烯烃化，Sharpless不对称二羟基化，环氧化，2,3-环氧醇的反式区域选择性开放，Horner-Wadsworth-Emmons（HWE）烯烃化和酰胺偶联是关键步骤。酰胺生物碱1 - 3用于抗结肠癌的人癌细胞系首次其抗癌活性（HT-29），乳腺癌（MCF-7）和肺（A-549）进行评价。