sodium salt of (2S)-bornane-2,10-sultam

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: sodium salt of (2S)-bornane-2,10-sultam
• 英文别名: (+)-camphorsultam sodium salt；sodium;(1R,5S,7S)-10,10-dimethyl-3lambda6-thia-4-azanidatricyclo[5.2.1.01,5]decane 3,3-dioxide；sodium;(1R,5S,7S)-10,10-dimethyl-3λ6-thia-4-azanidatricyclo[5.2.1.01,5]decane 3,3-dioxide
• 化学式: C₁₀H₁₆NO₂S*Na
• 分子量: 237.298
• InChiKey: QRMBKSPHDQRFFP-KBMNZXMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium salt of (2S)-bornane-2,10-sultam 在 silver-graphite 、 草酰氯 、 苯甲醛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1,6-Bis-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,5-dimethylene-hexane-1,6-dione
  参考文献：
  名称：

  Enantioselective Dreiding-Schmidt reactions: asymmetric synthesis and analysis of α-methylene-γ-butyrolactones

  摘要：

  The zinc/silver-graphite mediated Dreiding-Schmidt reactions between aldehydes and the 2-bromomethyl-acrylate derived sultamamides (+)/(-)-28 or (+)/(-)-30 gave the corresponding substituted alpha-methylene-gamma-butyrolactones with ee's up to 90%. Enantiomerically pure compounds were obtained by semipreparative HPLC using a chiral stationary phase. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00166-3

文献信息

• CDP840. A prototype of a novel class of orally active anti-Inflammatory phosphodiesterase 4 inhibitors
  作者：R.P. Alexander、G.J. Warrellow、M.A.W. Eaton、E.C. Boyd、J.C. Head、J.R. Porter、J.A. Brown、J.T. Reuberson、B. Hutchinson、P. Turner、B. Boyce、D. Barnes、B. Mason、A. Cannell、R.J. Taylor、A. Zomaya、A. Millican、J. Leonard、R. Morphy、M. Wales、M. Perry、R.A. Allen、N. Gozzard、B. Hughes、G. Higgs

  DOI：10.1016/s0960-894x(02)00202-0

  日期：2002.6

  The discovery, synthesis and biological activity of a series of triarylethane phosphodiesterase 4 inhibitors is described. Structure-activity relationship studies are presented for CDP840 29), a potent, chiral, selective inhibitor of PDE 4 (IC50 4nM). CDP840 is non-emetic in the ferret at 30 mg kg(-1) (po), active in models of inflammation and reverses ozone-induced bronchial hyperreactivity in the guinea pig. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Aminomethylation of chiral silyl enol ethers: access to β2-homotryptophane and β2-homolysine derivatives
  作者：Roba Moumné、Maud Larregola、Youcef Boutadla、Solange Lavielle、Philippe Karoyan

  DOI：10.1016/j.tetlet.2008.05.131

  日期：2008.8

  We describe here the aminomethylation of chiral silyl enol ether derivatives using iminium ion. The choice of judicious precursors with adequate protecting groups for the silylation/aminomethylation step was required to achieve the synthesis of beta(2)-homotryptophane in few steps. The same methodology was used to prepare a beta(2)-homolysine derivative. (C) 2008 Elsevier Ltd. All rights reserved.
• Enantioselective Dreiding-Schmidt reactions: asymmetric synthesis and analysis of α-methylene-γ-butyrolactones
  作者：René Csuk、Christina Schröder、Sonja Hutter、Kristina Mohr

  DOI：10.1016/s0957-4166(97)00166-3

  日期：1997.5

  The zinc/silver-graphite mediated Dreiding-Schmidt reactions between aldehydes and the 2-bromomethyl-acrylate derived sultamamides (+)/(-)-28 or (+)/(-)-30 gave the corresponding substituted alpha-methylene-gamma-butyrolactones with ee's up to 90%. Enantiomerically pure compounds were obtained by semipreparative HPLC using a chiral stationary phase. (C) 1997 Elsevier Science Ltd.