(1R,2R,6R,7R,8R,9R)-6-Isopropyl-3,9-dimethyl-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-en-10-one | 672904-60-8

• 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: (1R,2R,6R,7R,8R,9R)-6-Isopropyl-3,9-dimethyl-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-en-10-one
• 英文别名: (1R,2R,6R,7R,8R,9R)-3,9-dimethyl-6-propan-2-yl-12-oxatricyclo[6.3.1.02,7]dodec-3-en-10-one
• CAS: 672904-60-8
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: SCKIRXVEFTVTPP-YPVLBCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,6R,7R,8R,9R)-6-Isopropyl-3,9-dimethyl-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-en-10-one 在 disodium hydrogenphosphate 、 三氟过氧乙酸 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(1R,2S,3R,5S,7R,8R,9R,10R)-3,10-dimethyl-7-propan-2-yl-4,13-dioxatetracyclo[7.3.1.02,8.03,5]tridecan-11-one
  参考文献：
  名称：

  A General Route toward the Synthesis of the Cladiellin Skeleton Utilizing a SmI₂-Mediated Cyclization

  摘要：

  [graphics]An efficient synthesis of the cladiellin skeleton is reported utilizing methods that were previously developed in this laboratory. The approach is based on a SmI2-mediated cyclization reaction for the construction of the oxacyclononane unit. A [4 + 3] annulation strategy was used to create the octahydroisobenzofuran moiety. This route provides the cladiellin skeleton in only 14 steps without the use of protecting groups. The present approach also enabled the synthesis of the 3,7-diastereomer of the natural product polyanthellin A.

  DOI：

  10.1021/jo052290d
• 作为产物：
  描述：

  (1R,2R,6R,7R,8R,9S)-6-Isopropyl-3,9-dimethyl-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-en-10-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以73%的产率得到(1R,2R,6R,7R,8R,9R)-6-Isopropyl-3,9-dimethyl-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-en-10-one
  参考文献：
  名称：

  通往 Eunicellin 二萜的一般路线：Deacetoxyalcyonin Acetate 的不对称全合成

  摘要：

  报道了一种利用 TiCl4 介导的 [4+3] 环化处理加氢异苯并呋喃核的新方法。这种 [4+3] 环化方案提供了一条通向存在于单胞菌素二萜中的氢化异苯并呋喃核心的简短通用途径。使用这种环化，已经实现了单胞菌素家族成员醋酸脱乙酰氧基丙氨酸的短合成（17 步）。

  DOI：

  10.1021/ja0398464

文献信息

• A General Route toward the Synthesis of the Cladiellin Skeleton Utilizing a SmI₂-Mediated Cyclization
  作者：Gary A. Molander、Barbara Czakó、David J. St. Jean

  DOI：10.1021/jo052290d

  日期：2006.2.1

  [graphics]An efficient synthesis of the cladiellin skeleton is reported utilizing methods that were previously developed in this laboratory. The approach is based on a SmI2-mediated cyclization reaction for the construction of the oxacyclononane unit. A [4 + 3] annulation strategy was used to create the octahydroisobenzofuran moiety. This route provides the cladiellin skeleton in only 14 steps without the use of protecting groups. The present approach also enabled the synthesis of the 3,7-diastereomer of the natural product polyanthellin A.
• Toward a General Route to the Eunicellin Diterpenes:  The Asymmetric Total Synthesis of Deacetoxyalcyonin Acetate
  作者：Gary A. Molander、David J. St. Jean、Julia Haas

  DOI：10.1021/ja0398464

  日期：2004.2.1

  [4+3] annulation is reported. This [4+3] annulation protocol provides a short, general route to the hydroisobenzofuran core present in the eunicellin diterpenes. Using this annulation, a short synthesis (17 steps) of deacetoxyalcyonin acetate, a member of the eunicellin family, has been achieved.

  报道了一种利用 TiCl4 介导的 [4+3] 环化处理加氢异苯并呋喃核的新方法。这种 [4+3] 环化方案提供了一条通向存在于单胞菌素二萜中的氢化异苯并呋喃核心的简短通用途径。使用这种环化，已经实现了单胞菌素家族成员醋酸脱乙酰氧基丙氨酸的短合成（17 步）。