(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-fluoro-2-methyl-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester | 130594-01-3

• 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: (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-fluoro-2-methyl-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (2S)-3-[tert-butyl(dimethyl)silyl]oxy-2-fluoro-2-methylpropanoate
• CAS: 130594-01-3
• 化学式: C₂₆H₄₃FO₃Si
• 分子量: 450.71
• InChiKey: AYKKHDASDNKVIR-XTOGBABISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-Chlorocarbonyl-2-fluoro-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 在 4-二甲氨基吡啶 tetrabutylammonium borohydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-fluoro-2-methyl-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
  参考文献：
  名称：

  Ihara, Masataka; Taniguchi, Nobuaki; Kai, Tomoko, Journal of the Chemical Society. Perkin transactions I, 1992, # 2, p. 221 - 228

  摘要：

  DOI：

文献信息

• Influence of a 2-fluoro substituent on diastereoselectivity in the 1,3-dipolar cycloadditions of nitrones
  作者：Masataka Ihara、Yuko Tanaka、Nobuyuki Takahashi、Yuji Tokunaga、Keiichiro Fukumoto

  DOI：10.1039/a702810e

  日期：——

  It is clear that the role of 1,2-asymmetric induction on the 1,3-dipolar cycloaddition of nitrones is influenced by the presence of a fluorine atom at the C-2 position. 2-Fluoro nitrones, synthesized by three different methods, have been subjected to the intermolecular 1,3-dipolar cycloaddition with ethyl vinyl ether. The stereostructures of isoxazolidines formed were determined by their conversion into 2,7-dioxa-6-azabicyclo[3.2.1]octanes. The diastereoselectivity of 2-fluoro nitrones was the reverse of that of the corresponding 2-hydro nitrones. This fact supports that the conformation with relief from the dipole repulsion between the fluorine atom and the oxygen atom of the nitrone is a preferred one for 2-fluoro nitrones, while the corresponding 2-hydro nitrones adopt the conformation with the least 1,3-allylic strain.

  很明显，在氮酮的1,3-偶极环加成反应中，1,2-不对称诱导作用受到C-2位置氟原子存在的影响。通过三种不同方法合成的2-氟氮酮，与乙烯基乙醚进行了分子间的1,3-偶极环加成反应。所得异恶唑烷的立体结构通过其转化为2,7-二氧-6-氮杂双环[3.2.1]辛烷来确定。2-氟氮酮的非对映选择性与相应的2-羟氮酮相反。这一事实支持以下观点：氟原子与氮酮氧原子之间偶极排斥得到缓解的构象是2-氟氮酮的优选构象，而相应的2-羟氮酮则倾向于采取1,3-同系物应变最小的构象。
• Ihara, Masataka; Taniguchi, Nobuaki; Kai, Tomoko, Journal of the Chemical Society. Perkin transactions I, 1992, # 2, p. 221 - 228
  作者：Ihara, Masataka、Taniguchi, Nobuaki、Kai, Tomoko、Satoh, Ken、Fukumoto, Keiichiro

  DOI：——

  日期：——