[1-13C]-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde | 668988-69-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [1-13C]-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde
• 英文别名: [1-(13)C]-3-(tert-butyldimethylsilyloxy)propanal
• CAS: 668988-69-0
• 化学式: C₉H₂₀O₂Si
• 分子量: 189.331
• InChiKey: WGWCJTNWUFFGFH-CDYZYAPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [1-13C]-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以89%的产率得到[1-(13)C]-3-(tert-butyldimethylsilyloxy)propan-1-ol
  参考文献：
  名称：

  Enantioselective Syntheses of α-Fmoc-Pbf-[2-¹³C]-l-arginine and Fmoc-[1,3-¹³C₂]-l-proline and Incorporation into the Neurotensin Receptor 1 Ligand, NT₈₋₁₃

  摘要：

  Enantioselective syntheses of selectively labeled, orthogonally protected [2-C-13]L-arginine and [1,3-C-13(2)]-L-proline are described from the commercially available precursors [2-C-13]bromoacetic acid and potassium [C-13]cyanide, Interestingly the enhanced signal assigned to C-2 in the C-13 NMR spectrum of alpha-Fmoc-Pbf-[2-C-13]-L-arginine was very broad at room temperature. The two Fmoc-labeled amino acids were used to prepare [2-C-13]-Arg9 and [1,3-C-13(2)]-Pro 10 labeled ligand (NT8-13) by manual Fmoc-SPSS.

  DOI：

  10.1021/jo9014497
• 作为产物：
  描述：

  [1-13C]-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以98%的产率得到[1-13C]-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde
  参考文献：
  名称：

  Synthesis of Site-Specifically Labeled Arachidonic Acids as Mechanistic Probes for Prostaglandin H Synthase

  摘要：

  Prostaglandin H synthase catalyzes the first committed step in the biosynthesis of prostaglandins and thromboxane. Herein we report the synthesis of four site-specifically labeled arachidonic acids for investigation of the radical intermediate formed during this enzymatic reaction. Two compounds were prepared using a common C9-C11 fragment, while another target was synthesized using a previously reported advanced intermediate. An alkyne coupling followed by hydrogenation and Wittig reaction was used to prepare the final labeled substrate.

  DOI：

  10.1021/ol0361711