(5R,6R)-3-methyl-5-(methoxymethoxy)-6-(pivaloyloxy)deca-1,2-dien-8-yne | 1006369-90-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5R,6R)-3-methyl-5-(methoxymethoxy)-6-(pivaloyloxy)deca-1,2-dien-8-yne
• CAS: 1006369-90-9
• 化学式: C₁₈H₂₈O₄
• 分子量: 308.418
• InChiKey: WUKOPGWRADJEGC-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,6R)-3-methyl-5-(methoxymethoxy)-6-(pivaloyloxy)deca-1,2-dien-8-yne 、 一氧化碳 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,3-双(二苯基膦)丙烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以96%的产率得到(4R,5R)-2,8-dimethyl-4-(methoxymethoxy)-5-(pivaloyloxy)-bicyclo[5.3.0]deca-1,7-dien-9-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
• 作为产物：
  描述：

  、 甲基锂 在 copper(l) cyanide 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 以450 mg的产率得到(5R,6R)-3-methyl-5-(methoxymethoxy)-6-(pivaloyloxy)deca-1,2-dien-8-yne
  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