(2E,6E)-10-hydroxy-3,7-dimethyldeca-2,6-dienyl acetate | 917611-79-1

• 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: (2E,6E)-10-hydroxy-3,7-dimethyldeca-2,6-dienyl acetate
• 英文别名: [(2E,6E)-10-hydroxy-3,7-dimethyldeca-2,6-dienyl] acetate
• CAS: 917611-79-1
• 化学式: C₁₄H₂₄O₃
• 分子量: 240.343
• InChiKey: WUPJVHZBVHBVCC-IWFZMGPQSA-N

物化性质

• 沸点：
  347.3±30.0 °C(Predicted)
• 密度：
  0.971±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,6E)-10-hydroxy-3,7-dimethyldeca-2,6-dienyl acetate 在 咪唑 、 18-冠醚-6 、 四丁基氟化铵 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.17h， 生成 6,10-dimethyl-13-(4-methylphenyl)trideca-6,10-dien-2-one
  参考文献：
  名称：

  Catalytic Diastereoselective Polycyclization of Homo(polyprenyl)arene Analogues Bearing Terminal Siloxyvinyl Groups

  摘要：

  Highly diastereoselective polycyclization of homo(polyprenyl) arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4 alpha(equatorial)- and 4 beta(axial)-siloxypolycycles as major isomers, respectively. The strong nucleophilicity of pro-C(9), a (6E) geometry, and a bulky silyl group effectively favored the 4 alpha-preference, whereas the weak nucleophilicity of pro-C(9), a (6Z)-geometry, and less steric hindrance of a silyl group favored the 4 beta-preference.

  DOI：

  10.1021/ol062378t
• 作为产物：
  描述：

  (2E,6E)-10,11-环氧-3,7,11-三甲基-2,6-十二碳二烯-1-醇 在 吡啶 、 sodium tetrahydroborate 、 过碘酸 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 5.5h， 生成 (2E,6E)-10-hydroxy-3,7-dimethyldeca-2,6-dienyl acetate
  参考文献：
  名称：

  Catalytic Diastereoselective Polycyclization of Homo(polyprenyl)arene Analogues Bearing Terminal Siloxyvinyl Groups

  摘要：

  Highly diastereoselective polycyclization of homo(polyprenyl) arene analogues bearing terminal siloxyvinyl groups was catalyzed by tin(IV) chloride (10 mol %). The cyclizations of tert-butyldiphenylsilyl and triisopropylsilyl polyenol ethers gave 4 alpha(equatorial)- and 4 beta(axial)-siloxypolycycles as major isomers, respectively. The strong nucleophilicity of pro-C(9), a (6E) geometry, and a bulky silyl group effectively favored the 4 alpha-preference, whereas the weak nucleophilicity of pro-C(9), a (6Z)-geometry, and less steric hindrance of a silyl group favored the 4 beta-preference.

  DOI：

  10.1021/ol062378t

文献信息

• Farnesyl Diphosphate Analogues with ω-Bioorthogonal Azide and Alkyne Functional Groups for Protein Farnesyl Transferase-Catalyzed Ligation Reactions
  作者：Guillermo R. Labadie、Rajesh Viswanathan、C. Dale Poulter

  DOI：10.1021/jo7017747

  日期：2007.11.1

  [Graphics]Eleven farnesyl diphosphate analogues, which contained (omega-azide or alkyne substituents suitable for bioorthogonal Staudinger and Huisgen [3 + 2] cycloaddition coupling reactions, were synthesized. The analogues were evaluated as substrates for the alkylation of peptide cosubstrates by yeast protein farnesyl transferase. Five of the diphosphates were good alternative substrates for farnesyl diphosphate (FPP). Steady-state kinetic constants were measured for the active compounds, and the products were characterized by HPLC and LC-MS. Two of the analogues gave steady-state kinetic parameters (k(cat) and K-m) very similar to those of the natural substrate.
• A general synthetic method for 2,6-cyclodecadienone system by intramolecular alkylation of protected cyanohydrins
  作者：Takashi Takahashi、Hisao Nemoto、Jiro Tsuji

  DOI：10.1016/s0040-4039(00)81828-6

  日期：1983.1