5-Benzylidene-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 5-Benzylidene-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one
• 化学式: C₁₃H₁₃NOS₂
• 分子量: 263.384
• InChiKey: BGVUDYUGHVVZFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Benzylidene-3-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-4-one 、 (2R,3S)-2-methyl-4-nitro-3-phenylbutyraldehyde 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 2.0h， 生成 、
  参考文献：
  名称：

  通过有机催化级联反应不对称合成包含六个连续立体中心的类似环己烷的药物螺旋环支架。

  摘要：

  AbstractDrug‐like spirocyclic scaffolds have been prepared asymmetrically by fusing fully functionalized cyclohexanes with medicinally important pyrazolone, rhodanine, barbituric acid or indandione moieties. This approach utilizes an organocatalytic tandem Michael–Michael–aldol reaction that yields diverse chiral spirocyclic backbones containing six contiguous stereogenic centers and multiple functional groups. The target compounds are generated in good yield and with high stereoselectivity (up to 99 % ee and 95:5 dr). Intriguingly, diastereocontrol of the spiro‐products changes depending on the substrate.magnified image

  DOI：

  10.1002/adsc.201400764

文献信息

• Asymmetric Synthesis of Cyclohexane-Fused Drug-Like Spirocyclic Scaffolds Containing Six Contiguous Stereogenic Centers<i>via</i>Organocatalytic Cascade Reactions
  作者：Bo Han、Wei Huang、Wen Ren、Gu He、Jin-hui Wang、Cheng Peng

  DOI：10.1002/adsc.201400764

  日期：2015.2.9

  AbstractDrug‐like spirocyclic scaffolds have been prepared asymmetrically by fusing fully functionalized cyclohexanes with medicinally important pyrazolone, rhodanine, barbituric acid or indandione moieties. This approach utilizes an organocatalytic tandem Michael–Michael–aldol reaction that yields diverse chiral spirocyclic backbones containing six contiguous stereogenic centers and multiple functional groups. The target compounds are generated in good yield and with high stereoselectivity (up to 99 % ee and 95:5 dr). Intriguingly, diastereocontrol of the spiro‐products changes depending on the substrate.magnified image