(8'R,8a'S)-(+)-8,8a'-dimethyl-1',3',4',7',8',8a'-hexahydrospiro[1,3-dioxolane-2,2'(6'H)naphthalen]-6'-one | 73466-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (8'R,8a'S)-(+)-8,8a'-dimethyl-1',3',4',7',8',8a'-hexahydrospiro[1,3-dioxolane-2,2'(6'H)naphthalen]-6'-one
• 英文别名: (4'R,4'aS)-4',4'a-dimethylspiro[1,3-dioxolane-2,6'-4,5,7,8-tetrahydro-3H-naphthalene]-2'-one
• CAS: 73466-00-9
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: AMJTUKHPRGDKMK-MFKMUULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8'R,8a'S)-(+)-8,8a'-dimethyl-1',3',4',7',8',8a'-hexahydrospiro[1,3-dioxolane-2,2'(6'H)naphthalen]-6'-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以79%的产率得到(6'S,8'R,8a'S)-(+)-8,8a'-dimethyl-3',4',6',7',8',8a'-hexahydrospiro[1,3-dioxolane-2,2'(1'H)naphthalen]-6'-ol
  参考文献：
  名称：

  Enantioselective imine Michael reaction for the preparation of the (8′R,8a′S)-8,8a′-dimethyl-1′,3′,4′,7′,8′,8a′-hexahydrospiro[1,3-dioxolane-2,2′(6′H)naphthalen]-6′-one building block. A formal synthesis of (+)-valencenol

  摘要：

  The enantioselective Michael addition of a chiral imine of 4-protected 2-methylcyclohexane-1,4-dione to phenyl crotonate led after cyclization. to the corresponding bicyclic lactam. Reductive cleavage of the chiral moiety followed by saponification gave the corresponding keto-acid, which was cyclized to afford a lactone. Belleau-Fujimoto reaction of the lactone then led to the title building block (diastereoselectivity 96:4, e.e. > 98%) in 11% overall yield from the starting dione. (8R, 8aS)-(+)-8,8a-Dimethyl-3,4,6,7,8,8a-hexahydronaphthalen-2 (1H)-one was obtained after reduction of the carbonyl group, acetylation, and reductive cleavage-deprotection (52% overall yield), representing a formal synthesis of (+)-valencenol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00289-0
• 作为产物：
  描述：

  (βR,7S)-β,7-dimethyl-8-oxo-1,4-dioxaspiro[4,5]decane-7-propanoic acid 在 正丁基锂 、 sodium acetate 作用下， 以 四氢呋喃 、 正己烷 、 乙酸酐 为溶剂， 反应 5.58h， 生成 (8'R,8a'S)-(+)-8,8a'-dimethyl-1',3',4',7',8',8a'-hexahydrospiro[1,3-dioxolane-2,2'(6'H)naphthalen]-6'-one
  参考文献：
  名称：

  Enantioselective imine Michael reaction for the preparation of the (8′R,8a′S)-8,8a′-dimethyl-1′,3′,4′,7′,8′,8a′-hexahydrospiro[1,3-dioxolane-2,2′(6′H)naphthalen]-6′-one building block. A formal synthesis of (+)-valencenol

  摘要：

  The enantioselective Michael addition of a chiral imine of 4-protected 2-methylcyclohexane-1,4-dione to phenyl crotonate led after cyclization. to the corresponding bicyclic lactam. Reductive cleavage of the chiral moiety followed by saponification gave the corresponding keto-acid, which was cyclized to afford a lactone. Belleau-Fujimoto reaction of the lactone then led to the title building block (diastereoselectivity 96:4, e.e. > 98%) in 11% overall yield from the starting dione. (8R, 8aS)-(+)-8,8a-Dimethyl-3,4,6,7,8,8a-hexahydronaphthalen-2 (1H)-one was obtained after reduction of the carbonyl group, acetylation, and reductive cleavage-deprotection (52% overall yield), representing a formal synthesis of (+)-valencenol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00289-0

文献信息

• Enantioselective imine Michael reaction for the preparation of the (8′R,8a′S)-8,8a′-dimethyl-1′,3′,4′,7′,8′,8a′-hexahydrospiro[1,3-dioxolane-2,2′(6′H)naphthalen]-6′-one building block. A formal synthesis of (+)-valencenol
  作者：Gilbert Revial、Ivan Jabin、Michaël Redolfi、Michel Pfau

  DOI：10.1016/s0957-4166(01)00289-0

  日期：2001.7

  The enantioselective Michael addition of a chiral imine of 4-protected 2-methylcyclohexane-1,4-dione to phenyl crotonate led after cyclization. to the corresponding bicyclic lactam. Reductive cleavage of the chiral moiety followed by saponification gave the corresponding keto-acid, which was cyclized to afford a lactone. Belleau-Fujimoto reaction of the lactone then led to the title building block (diastereoselectivity 96:4, e.e. > 98%) in 11% overall yield from the starting dione. (8R, 8aS)-(+)-8,8a-Dimethyl-3,4,6,7,8,8a-hexahydronaphthalen-2 (1H)-one was obtained after reduction of the carbonyl group, acetylation, and reductive cleavage-deprotection (52% overall yield), representing a formal synthesis of (+)-valencenol. (C) 2001 Elsevier Science Ltd. All rights reserved.