(4S,5S,7R,13R,E)-14-pentyl-4,5,7-tris(triisopropylsilyloxy)oxacyclotetradec-3-en-2-one | 1374332-88-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (4S,5S,7R,13R,E)-14-pentyl-4,5,7-tris(triisopropylsilyloxy)oxacyclotetradec-3-en-2-one
• CAS: 1374332-88-3
• 化学式: C₄₅H₉₂O₅Si₃
• 分子量: 797.479
• InChiKey: KDJCGMGUVAFAPD-GYOKMHRNSA-N

物化性质

• 沸点：
  702.3±60.0 °C(predicted)
• 密度：
  0.91±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  15.07
• 重原子数：
  53.0
• 可旋转键数：
  19.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4S,5S,7R,13R,E)-14-pentyl-4,5,7-tris(triisopropylsilyloxy)oxacyclotetradec-3-en-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.08h， 以6.4 mg的产率得到(5S,6S,8R,14R,E)-5,6,8-trihydroxy-14-pentyloxacyclotetradec-3-en-2-one
  参考文献：
  名称：

  Minimal Fluorous Tagging Strategy that Enables the Synthesis of the Complete Stereoisomer Library of SCH725674 Macrolactones

  摘要：

  Four mixtures of four fluorous-tagged quasiisomers have been synthesized, demixed, and detagged to make all 16 stereoisomers of the macrocyclic lactone natural product Sch725674. A new bare-minimum tagging pattern needs only two tags one fluorous and one nonfluorous-to encode four isomers. The structure of Sch725674 is assigned as (5R,6S,8R,14R,E)-5,6,8-trihydroxy-14-pentyloxacyclotetradec-3-en-2-one. Various comparisons of spectra of 32 lactones (16 with tags, 16 without) and 16 ester precursors (8 with tags, 8 without) provide insights into when and why related compounds have the same or different spectra.

  DOI：

  10.1021/ja302260d
• 作为产物：
  描述：

  (4S,5S,7R)-((R)-dec-1-en-5-yl) 4,5,7-tris(triisopropylsilyloxy)deca-2,9-dienoate 、 C₄₈H₉₁F₅O₅Si₃ 、 C₄₉H₈₈F₁₀O₅Si₃ 、 C₅₀H₈₅F₁₅O₅Si₃ 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 Pd/SrCO₃ 、 氢气 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 反应 49.0h， 生成 (4S,5S,7R,13R,E)-14-pentyl-4,5,7-tris(triisopropylsilyloxy)oxacyclotetradec-3-en-2-one 、 、 、
  参考文献：
  名称：

  Minimal Fluorous Tagging Strategy that Enables the Synthesis of the Complete Stereoisomer Library of SCH725674 Macrolactones

  摘要：

  Four mixtures of four fluorous-tagged quasiisomers have been synthesized, demixed, and detagged to make all 16 stereoisomers of the macrocyclic lactone natural product Sch725674. A new bare-minimum tagging pattern needs only two tags one fluorous and one nonfluorous-to encode four isomers. The structure of Sch725674 is assigned as (5R,6S,8R,14R,E)-5,6,8-trihydroxy-14-pentyloxacyclotetradec-3-en-2-one. Various comparisons of spectra of 32 lactones (16 with tags, 16 without) and 16 ester precursors (8 with tags, 8 without) provide insights into when and why related compounds have the same or different spectra.

  DOI：

  10.1021/ja302260d