(S)-9,9-dimethyl-4-triisopropylsilanyloxymethyl-undeca-4,6-dien-10-yn-2-ol | 953814-57-8

• 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: (S)-9,9-dimethyl-4-triisopropylsilanyloxymethyl-undeca-4,6-dien-10-yn-2-ol
• 英文别名: (2S,4Z,6E)-9,9-dimethyl-4-[tri(propan-2-yl)silyloxymethyl]undeca-4,6-dien-10-yn-2-ol
• CAS: 953814-57-8
• 化学式: C₂₃H₄₂O₂Si
• 分子量: 378.671
• InChiKey: MWFUPCBDHQYFEJ-BRAUPHFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  (S)-9,9-dimethyl-4-triisopropylsilanyloxymethyl-undeca-4,6-dien-10-yn-2-ol 、 (S)-(+)-alpha-甲氧基苯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以69%的产率得到(S,S)-methoxyphenylacetic acid 1,8,8-trimethyl-3-triisopropylsilanyloxymethyl-deca-3,6-dien-19-ynyl ester
  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：

  (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 丙酮 为溶剂， 反应 5.0h， 以8.0 mg的产率得到(S)-9,9-dimethyl-4-triisopropylsilanyloxymethyl-undeca-4,6-dien-10-yn-2-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

文献信息

• Total Synthesis of (+)-Frondosin A. Application of the Ru-Catalyzed [5+2] Cycloaddition
  作者：Barry M. Trost、Yimin Hu、Daniel B. Horne

  DOI：10.1021/ja073272b

  日期：2007.9.1

  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.