(1S,2R,2'S,5S,5'R,7S,8R)-5'-methyl-2'-propan-2-ylspiro[4-oxatricyclo[6.2.1.02,7]undec-9-ene-5,1'-cyclohexane]-3,6-dione | 173928-57-9

• 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: (1S,2R,2'S,5S,5'R,7S,8R)-5'-methyl-2'-propan-2-ylspiro[4-oxatricyclo[6.2.1.02,7]undec-9-ene-5,1'-cyclohexane]-3,6-dione
• CAS: 173928-57-9
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: OGLOADOKBNRROG-JBLOWMKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,2'S,5S,5'R,7S,8R)-5'-methyl-2'-propan-2-ylspiro[4-oxatricyclo[6.2.1.02,7]undec-9-ene-5,1'-cyclohexane]-3,6-dione 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以87%的产率得到(1S,2S,5R)-1-[hydroxy-[(1R,2S,3R,4S)-3-(hydroxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]methyl]-5-methyl-2-propan-2-ylcyclohexan-1-ol
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions with a chiral spirodione, (6S, 7S, 10R)-7-Isopropyl-10-methyl-1-oxaspiro[5.5]undec-3-ene-2,5-dione

  摘要：

  The synthesis of the title spirodione, a new class of auxiliary based chiral synthon, using (-)-menthone having a unique carbon-carbon bond is described. Diels-Alder reactions were carried out with variety of dienes using the title auxiliary as a chiral dienophile in the presence of diethyl aluminium chloride as Lewis acid catalyst to afford the cycloadduct with good diastereoselectivity. The configurations of the chiral synthon and cycloadducts were determined by X-ray crystallography. Methodology for detachment of the chiral auxiliary from the cycloadducts has been developed.

  DOI：

  10.1016/0957-4166(95)00393-2
• 作为产物：
  描述：

  trans-1-(2-furyl)-menthan-1-ol 在 Jones'reagent 、 氯化二乙基铝 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 8.5h， 生成 (1S,2R,2'S,5S,5'R,7S,8R)-5'-methyl-2'-propan-2-ylspiro[4-oxatricyclo[6.2.1.02,7]undec-9-ene-5,1'-cyclohexane]-3,6-dione
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions with a chiral spirodione, (6S, 7S, 10R)-7-Isopropyl-10-methyl-1-oxaspiro[5.5]undec-3-ene-2,5-dione

  摘要：

  The synthesis of the title spirodione, a new class of auxiliary based chiral synthon, using (-)-menthone having a unique carbon-carbon bond is described. Diels-Alder reactions were carried out with variety of dienes using the title auxiliary as a chiral dienophile in the presence of diethyl aluminium chloride as Lewis acid catalyst to afford the cycloadduct with good diastereoselectivity. The configurations of the chiral synthon and cycloadducts were determined by X-ray crystallography. Methodology for detachment of the chiral auxiliary from the cycloadducts has been developed.

  DOI：

  10.1016/0957-4166(95)00393-2

文献信息

• Asymmetric Diels-Alder reactions with a chiral spirodione, (6S, 7S, 10R)-7-Isopropyl-10-methyl-1-oxaspiro[5.5]undec-3-ene-2,5-dione
  作者：Chimmanamada U. Dinesh、Pradeep Kumar、Ravinder S. Reddy、Bipin Pandey、Vedavathi G. Puranik

  DOI：10.1016/0957-4166(95)00393-2

  日期：1995.12

  The synthesis of the title spirodione, a new class of auxiliary based chiral synthon, using (-)-menthone having a unique carbon-carbon bond is described. Diels-Alder reactions were carried out with variety of dienes using the title auxiliary as a chiral dienophile in the presence of diethyl aluminium chloride as Lewis acid catalyst to afford the cycloadduct with good diastereoselectivity. The configurations of the chiral synthon and cycloadducts were determined by X-ray crystallography. Methodology for detachment of the chiral auxiliary from the cycloadducts has been developed.