(1S,2R,3R,6S,7S,8R)-tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-diol | 164453-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3R,6S,7S,8R)-tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-diol
• CAS: 164453-61-6
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: WQYPBLXNPXDCOZ-PCKUECCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3R,6S,7S,8R)-tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-diol 以 丙酮 为溶剂， 反应 14.0h， 以81%的产率得到3α,6β-Dihydroxy-pentacyclo[6,2,1,0^2,7,0^4,10,0^5,9]undecan
  参考文献：
  名称：

  Facile stereoselective reductions of enediones and cage diketones suing sodium borohydride-cerium(III) chloride

  摘要：

  DOI：

  10.1021/jo00359a054
• 作为产物：
  描述：

  norbornenoquinone 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以82%的产率得到(1S,2R,3R,6S,7S,8R)-tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-diol
  参考文献：
  名称：

  Facile stereoselective reductions of enediones and cage diketones suing sodium borohydride-cerium(III) chloride

  摘要：

  DOI：

  10.1021/jo00359a054

文献信息

• Lipophilic Oligopeptides for Chemo- and Enantioselective Acyl Transfer Reactions onto Alcohols
  作者：Christian E. Müller、Daniela Zell、Radim Hrdina、Raffael C. Wende、Lukas Wanka、Sören M. M. Schuler、Peter R. Schreiner

  DOI：10.1021/jo401195c

  日期：2013.9.6

  Inspired by the extraordinary selectivities of acylases, we envisioned the use of lipophilic oligopeptidic organocatalysts for the acylative kinetic resolution/desymmetrization of rac- and meso-cycloalkane-1,2-diols. Here we describe in a full account the discovery and development process from the theoretical concept to the final catalyst, including scope and limitations. Competition experiments with various alcohols and electrophiles show the full potential of the employed oligopeptides. Additionally, we utilized NMR and IR-spectroscopic methods as well as computations to shed light on the factors responsible for the selectivity. The catalyst system can be readily modified to a multicatalyst by adding other catalytically active amino acids to the peptide backbone, enabling the stereoselective one-pot synthesis of complex molecules from simple starting materials.