1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazole-5-carbaldehyde | 635713-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazole-5-carbaldehyde
• 英文别名: 1-[[2-(Trimethylsilyl)ethyl]sulfonyl]-1h-indazole-5-carboxaldehyde；1-(2-trimethylsilylethylsulfonyl)indazole-5-carbaldehyde
• CAS: 635713-79-0
• 化学式: C₁₃H₁₈N₂O₃SSi
• 分子量: 310.449
• InChiKey: BHBKTBJBOCUECH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazole-5-carbaldehyde 、 (±)-Z-α-膦酰甘氨酸三甲酯 在 四甲基胍 作用下， 以 四氢呋喃 为溶剂， 反应 5.25h， 以92%的产率得到2-benzyloxycarbonylamino-3-[1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazol-5-yl]-acrylic acid methyl ester
  参考文献：
  名称：

  Catalytic Asymmetric Syntheses of Tyrosine Surrogates

  摘要：

  Amino acid esters 5-11 as tyrosine mimics have been synthesized in excellent enantioselectivity (up to 99.6% ee) and in good overall chemical yields. The key step in the sequence was the Burk's [Rh(COD)(2R,5R)-Et-DuPhos]BF(4)-catalyzed asymmetric hydrogenation of enamides with a variety of reactive functional groups.

  DOI：

  10.1021/jo801577t
• 作为产物：
  描述：

  1H-吲唑-5-甲醛 、 2-(三甲基硅基)乙烷磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以71%的产率得到1-(2-trimethylsilanyl-ethanesulfonyl)-1H-indazole-5-carbaldehyde
  参考文献：
  名称：

  Catalytic Asymmetric Syntheses of Tyrosine Surrogates

  摘要：

  Amino acid esters 5-11 as tyrosine mimics have been synthesized in excellent enantioselectivity (up to 99.6% ee) and in good overall chemical yields. The key step in the sequence was the Burk's [Rh(COD)(2R,5R)-Et-DuPhos]BF(4)-catalyzed asymmetric hydrogenation of enamides with a variety of reactive functional groups.

  DOI：

  10.1021/jo801577t

文献信息

• Catalytic Asymmetric Syntheses of Tyrosine Surrogates
  作者：Xiaojun Han、Rita L. Civiello、Haiquang Fang、Dedong Wu、Qi Gao、Prasad V. Chaturvedula、John E. Macor、Gene M. Dubowchik

  DOI：10.1021/jo801577t

  日期：2008.11.7

  Amino acid esters 5-11 as tyrosine mimics have been synthesized in excellent enantioselectivity (up to 99.6% ee) and in good overall chemical yields. The key step in the sequence was the Burk's [Rh(COD)(2R,5R)-Et-DuPhos]BF(4)-catalyzed asymmetric hydrogenation of enamides with a variety of reactive functional groups.