4-tert-butyldimethylsiloxydec-2-ynoic acid methyl ester | 804474-94-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-tert-butyldimethylsiloxydec-2-ynoic acid methyl ester
• 英文别名: methyl 4-((tert-butyldimethylsilyl)oxy)dec-2-ynoate；methyl 4-[tert-butyl(dimethyl)silyl]oxydec-2-ynoate
• CAS: 804474-94-0
• 化学式: C₁₇H₃₂O₃Si
• 分子量: 312.525
• InChiKey: IJTKNNWVNNLLTE-UHFFFAOYSA-N

物化性质

• 沸点：
  351.5±25.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-tert-butyldimethylsiloxydec-2-ynoic acid methyl ester 在 RhCl(PPh₃)3 、 氘 作用下， 以 苯 为溶剂， 以97%的产率得到[2,2,3,3-2H4]-4-tert-butyldimethylsiloxydec-2-ynoic acid methyl ester
  参考文献：
  名称：

  Synthesis of Deuterated γ-Lactones for Use in Stable Isotope Dilution Assays

  摘要：

  Two syntheses of deuterated gamma-lactones for use as internal standards in stable isotope dilution assays (SIDA) were developed. [2,2,3,3-H-2(4)]-gamma-Octa-, -gamma-deca-, and -gamma-dodecalactones with > 89% deuterium incorporation were prepared in 27, 17, and 19% overall yields, respectively, by the reduction of a doubly protected hydroxypropiolic acid with deuterium gas. [3,3,4-H-2(3)]-gamma-Octa- and -gamma-dodecalactones were prepared in 6 and 23% yields with > 92% deuterium incorporation by the free radical addition of 2-iodoacetamide to [1,1,2-H-2(3)]-1-hexene and [1,1,2-H-2(3)]-1-decene, respectively. Reaction yields were highly dependent upon the purity of the 1-alkene starting material. The deuterated gamma-lactones were evaluated as internal standards for SIDA.

  DOI：

  10.1021/jf048885b
• 作为产物：
  描述：

  庚醛 在 咪唑 、 N-甲基咪唑 、 diethylzinc 作用下， 以 正庚烷 、 二氯甲烷 为溶剂， 反应 15.25h， 生成 4-tert-butyldimethylsiloxydec-2-ynoic acid methyl ester
  参考文献：
  名称：

  A Redox Economical Synthesis of Bioactive 6,12-Guaianolides

  摘要：

  Syntheses of two 6,12-guaianolide analogs are reported within. The scope of the tandem allylboration/lactonization chemistry is expanded to provide a functionalized allene-yne-containing alpha-methylene butyrolactone that undergoes a Rh(I)-catalyzed cyclocarbonylation reaction to afford a 5-7-5 ring system. The resulting cycloadducts bear a structural resemblance to other NF-kappa B inhibitors such as cumambrin A and indeed were shown to inhibit NF-kappa B signaling and cancer cell growth.

  DOI：

  10.1021/ol400904y