(3R,7R,9S,10S)-12-(tert-butyldimethylsiloxy)-9,13-dimethyl-4-methylene-6-oxatricyclo[8.3.0.0^3,7]tetradec-13-en-5-one | 1006370-08-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3R,7R,9S,10S)-12-(tert-butyldimethylsiloxy)-9,13-dimethyl-4-methylene-6-oxatricyclo[8.3.0.0^3,7]tetradec-13-en-5-one
• 英文别名: (3aR,5S,5aS,9aR)-7-[tert-butyl(dimethyl)silyl]oxy-5,8-dimethyl-1-methylidene-3a,4,5,5a,6,7,9,9a-octahydroazuleno[6,5-b]furan-2-one
• CAS: 1006370-08-6
• 化学式: C₂₁H₃₄O₃Si
• 分子量: 362.585
• InChiKey: FLDUMTNKRGKAOB-PZCBKPRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,7R,9S,10S)-12-(tert-butyldimethylsiloxy)-9,13-dimethyl-4-methylene-6-oxatricyclo[8.3.0.0^3,7]tetradec-13-en-5-one 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以81%的产率得到achalensolide
  参考文献：
  名称：

  Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction

  摘要：

  [GRAPHICS]The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.

  DOI：

  10.1021/jo702330y
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以10.0 mg的产率得到(3R,7R,9S,10S)-12-(tert-butyldimethylsiloxy)-9,13-dimethyl-4-methylene-6-oxatricyclo[8.3.0.0^3,7]tetradec-13-en-5-one
  参考文献：
  名称：

  Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction

  摘要：

  [GRAPHICS]The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.

  DOI：

  10.1021/jo702330y

文献信息

• Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction
  作者：Toshiyuki Hirose、Naoki Miyakoshi、Chisato Mukai

  DOI：10.1021/jo702330y

  日期：2008.2.1

  [GRAPHICS]The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.