(1'S,4'R,5'S,9'S,10'R)-4',10'-dimethylspiro[cyclopropane-1,7'-tricyclo[7.2.1.01,5]dodecane]-12'-one | 299915-62-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'S,4'R,5'S,9'S,10'R)-4',10'-dimethylspiro[cyclopropane-1,7'-tricyclo[7.2.1.01,5]dodecane]-12'-one
• CAS: 299915-62-1
• 化学式: C₁₆H₂₄O
• 分子量: 232.366
• InChiKey: YOYWSFQGHXIHMI-WSGDXGOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1'S,4'R,5'S,9'S,10'R)-4',10'-dimethylspiro[cyclopropane-1,7'-tricyclo[7.2.1.01,5]dodecane]-12'-one 在 MMPP 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到(1S,4R,5S,9S,13R)-4,13-dimethylspiro[10-oxatricyclo[7.2.2.01,5]tridecane-7,1'-cyclopropane]-11-one
  参考文献：
  名称：

  Intramolecular 4 + 3 Cycloadditions. Aspects of Stereocontrol in the Synthesis of Cyclooctanoids. A Synthesis of (+)-Dactylol

  摘要：

  The judicious placement of stereocenters on precursors for 4 + 3 cycloaddition reactions can lead to high levels of stereocontrol in the 4 + 3 cycloaddition process of cyclopentenyl cations and tethered butadienes. This concept was successfully tested in the context of a synthesis of (+)-dactylol.

  DOI：

  10.1021/ol006390b
• 作为产物：
  描述：

  (2R)-2-甲基-5-氧环戊基甲酸甲酯 在 potassium cyanide 、 正丁基锂 、 三氟甲烷磺酰氯 、 diethylzinc 、 sodium hydride 、 lithium diisopropyl amide 作用下， 以 二甲基亚砜 为溶剂， 生成 (1'S,4'R,5'S,9'S,10'R)-4',10'-dimethylspiro[cyclopropane-1,7'-tricyclo[7.2.1.01,5]dodecane]-12'-one
  参考文献：
  名称：

  Intramolecular 4 + 3 Cycloadditions. Aspects of Stereocontrol in the Synthesis of Cyclooctanoids. A Synthesis of (+)-Dactylol

  摘要：

  The judicious placement of stereocenters on precursors for 4 + 3 cycloaddition reactions can lead to high levels of stereocontrol in the 4 + 3 cycloaddition process of cyclopentenyl cations and tethered butadienes. This concept was successfully tested in the context of a synthesis of (+)-dactylol.

  DOI：

  10.1021/ol006390b

文献信息

• Intramolecular [4 + 3] cycloadditions – Stereochemical issues in the cycloaddition reactions of cyclopentenyl cations – A synthesis of (+)-dactylol
  作者：Michael Harmata、Paitoon Rashatasakhon、Charles L Barnes

  DOI：10.1139/v06-122

  日期：2006.10.1

  Five cyclopentanones were prepared for the purpose of examining the effects of stereogenic centers on the course of the intramolecular [4 + 3] cycloaddition reactions of cyclopentenyl cations. One substrate reacted with very high levels of diastereoselectivity and was converted to (+)-dactylol. The cyclopentenone without stereogenic centers on the tether or the five-membered ring gave two cycloadducts

  为了检查立体中心对环戊烯基阳离子的分子内 [4 + 3] 环加成反应过程的影响，制备了五种环戊酮。一种底物以非常高的非对映选择性反应并转化为 (+)-dactylol。在系链或五元环上没有立体中心的环戊烯酮产生两个环加合物，内型异构体仅略微优于外型。其他底物反应的立体选择性通常从好到差。导致(+)-dactylol 的底物的差向异构体提供了环加合物的所有可能的异构体，具有相对较差的立体选择性。关键词：环加成，全合成，dactylol。
• Intramolecular 4 + 3 Cycloadditions. Aspects of Stereocontrol in the Synthesis of Cyclooctanoids. A Synthesis of (+)-Dactylol
  作者：Michael Harmata、Paitoon Rashatasakhon

  DOI：10.1021/ol006390b

  日期：2000.9.1

  The judicious placement of stereocenters on precursors for 4 + 3 cycloaddition reactions can lead to high levels of stereocontrol in the 4 + 3 cycloaddition process of cyclopentenyl cations and tethered butadienes. This concept was successfully tested in the context of a synthesis of (+)-dactylol.