(R,R)-5,5-dimethyl-1-(2-methyl-1-triisopropylsilanyloxymethyl-cyclopropyl)-hept-1-en-6-yn-3-ol | 953814-71-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R,R)-5,5-dimethyl-1-(2-methyl-1-triisopropylsilanyloxymethyl-cyclopropyl)-hept-1-en-6-yn-3-ol
• 英文别名: (E,3S)-5,5-dimethyl-1-[(1R,2R)-2-methyl-1-[tri(propan-2-yl)silyloxymethyl]cyclopropyl]hept-1-en-6-yn-3-ol
• CAS: 953814-71-6
• 化学式: C₂₃H₄₂O₂Si
• 分子量: 378.671
• InChiKey: KLIBEJMGKJOPIR-OUAJRZJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.17
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R,R)-5,5-dimethyl-1-(2-methyl-1-triisopropylsilanyloxymethyl-cyclopropyl)-hept-1-en-6-yn-3-ol 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到(1S,3aE,6S,7E,8aR)-3,3,6-trimethyl-7-((triisopropylsilanyloxy)methyl)-1,2,3,5,6,8a-hexahydro-azulen-1-ol
  参考文献：
  名称：

  Total Synthesis of (+)-Frondosin A. Application of the Ru-Catalyzed [5+2] Cycloaddition

  摘要：

  The first total synthesis of (+)-frondosin A was accomplished in 19 longest linear and 21 total steps from commercially available materials. The key features of the synthesis include a Ru-catalyzed [5+2] cycloaddition, a Claisen rearrangement, and a ring expansion to construct the core of the frondosin A in a diastereoselective and regioselective fashion. This is the first application of a Ru-catalyzed [5+2] cycloaddition in the total synthesis of a natural product. Through this synthesis, the absolute configuration of (+)-frondosin A was established.

  DOI：

  10.1021/ja073272b
• 作为产物：
  描述：

  (E)-5,5-dimethyl-1-((1R,2R)-2-methyl-1-((triisopropylsilanyloxy)methyl)-cyclopropyl)hept-1-en-6-yn-3-one 在 (S)-2-甲基-CBS-恶唑硼烷 儿萘酚硼烷 作用下， 以 二氯甲烷 为溶剂， 生成 (R,R)-5,5-dimethyl-1-(2-methyl-1-triisopropylsilanyloxymethyl-cyclopropyl)-hept-1-en-6-yn-3-ol 、 (R,R)-5,5-dimethyl-1-(2-methyl-1-triisopropylsilanyloxymethyl-cyclopropyl)-hept-1-en-6-yn-3-ol
  参考文献：
  名称：

  Total Synthesis of (+)-Frondosin A. Application of the Ru-Catalyzed [5+2] Cycloaddition

  摘要：

  The first total synthesis of (+)-frondosin A was accomplished in 19 longest linear and 21 total steps from commercially available materials. The key features of the synthesis include a Ru-catalyzed [5+2] cycloaddition, a Claisen rearrangement, and a ring expansion to construct the core of the frondosin A in a diastereoselective and regioselective fashion. This is the first application of a Ru-catalyzed [5+2] cycloaddition in the total synthesis of a natural product. Through this synthesis, the absolute configuration of (+)-frondosin A was established.

  DOI：

  10.1021/ja073272b