(3S,3aS,7aR)-3-(1-isopropylvinyl)-7a-methyloctahydro-4H-inden-4-one | 850195-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,3aS,7aR)-3-(1-isopropylvinyl)-7a-methyloctahydro-4H-inden-4-one
• 英文别名: (3S,3aS,7aR)-7a-methyl-3-(3-methylbut-1-en-2-yl)-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 850195-71-0
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: ZRIAQHLTBOMYTI-BPLDGKMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (3S,3aS,7aR)-3-(1-isopropylvinyl)-7a-methyloctahydro-4H-inden-4-one 在 正丁基锂 、 sodium methylate 、 臭氧 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 171.75h， 生成 2-methyl-1-[(3S,3aR,4R,7aR)-7a-methyloctahydrospiro[indene-4,2'-oxiran]-3-yl]propan-1-one
  参考文献：
  名称：

  Total syntheses of the sesquiterpenoids (+)-trans-dracunculifoliol and (+)-4-hydroxyoppositan-7-one

  摘要：

  Sesquiterpenoids (+)-trans-dracuncuflifoliol (1) and (+)-4-hydroxyoppositan-7-one (2) were prepared stereoselectively from enantiomerically pure (7aR)-7a-methyl-1,2,5,6,7,7a-hexahydro-4H-inden-4-one ((-)-6), whose synthesis was described herein. Conjugate addition of the organocopper (1) reagent 10 to (-)-6, followed by epimerization of the ring junction, generated 3 of the 4 contiguous chiral centers of both natural products. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.089
• 作为产物：
  描述：

  hexahydro-1,2,6,7,7a methyl-7a 4H-indenone-4 (ou methyl-7a Δ^3(3a)-hydrindenone-4) 在 正丁基锂 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 、 正戊烷 为溶剂， 反应 5.5h， 生成 (3S,3aS,7aR)-3-(1-isopropylvinyl)-7a-methyloctahydro-4H-inden-4-one
  参考文献：
  名称：

  Total syntheses of the sesquiterpenoids (+)-trans-dracunculifoliol and (+)-4-hydroxyoppositan-7-one

  摘要：

  Sesquiterpenoids (+)-trans-dracuncuflifoliol (1) and (+)-4-hydroxyoppositan-7-one (2) were prepared stereoselectively from enantiomerically pure (7aR)-7a-methyl-1,2,5,6,7,7a-hexahydro-4H-inden-4-one ((-)-6), whose synthesis was described herein. Conjugate addition of the organocopper (1) reagent 10 to (-)-6, followed by epimerization of the ring junction, generated 3 of the 4 contiguous chiral centers of both natural products. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.089

文献信息

• Total syntheses of the sesquiterpenoids (+)-trans-dracunculifoliol and (+)-4-hydroxyoppositan-7-one
  作者：Renata M. Oballa、Rebekah Carson、Susan Lait、Jay A. Cadieux、Joël Robichaud

  DOI：10.1016/j.tet.2005.01.089

  日期：2005.3

  Sesquiterpenoids (+)-trans-dracuncuflifoliol (1) and (+)-4-hydroxyoppositan-7-one (2) were prepared stereoselectively from enantiomerically pure (7aR)-7a-methyl-1,2,5,6,7,7a-hexahydro-4H-inden-4-one ((-)-6), whose synthesis was described herein. Conjugate addition of the organocopper (1) reagent 10 to (-)-6, followed by epimerization of the ring junction, generated 3 of the 4 contiguous chiral centers of both natural products. (c) 2005 Elsevier Ltd. All rights reserved.