(4S,5R,7S,13S,E)-4,5,7-trihydroxy-13-pentyloxacyclotetradec-2-en-1-one | 1374409-70-7

• 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,5R,7S,13S,E)-4,5,7-trihydroxy-13-pentyloxacyclotetradec-2-en-1-one
• 英文别名: (3E,5S,6R,8S,14S)-5,6,8-trihydroxy-14-pentyl-1-oxacyclotetradec-3-en-2-one
• CAS: 1374409-70-7
• 化学式: C₁₈H₃₂O₅
• 分子量: 328.449
• InChiKey: LEEBEEPDVOWSDN-HUIMAQOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (4S,5R,7S,13S,E)-13-pentyl-4,5-bis(triisopropylsilyloxy)-7-diisopropyl-(1,1,1,2,2-pentafluorobutylsilyloxy)-oxacyclo-tetra-dec-2-enone 在 盐酸 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 16.0h， 以17%的产率得到(4S,5R,7S,13S,E)-4,5,7-trihydroxy-13-pentyloxacyclotetradec-2-en-1-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

文献信息

• Minimal Fluorous Tagging Strategy that Enables the Synthesis of the Complete Stereoisomer Library of SCH725674 Macrolactones
  作者：Jared D. Moretti、Xiao Wang、Dennis P. Curran

  DOI：10.1021/ja302260d

  日期：2012.5.9

  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.