(4R',4a'S)-(-)-4',4a'-dimethyl-1'-[(1R)-1-phenylethyl]-1',3',4',4a',5',7'-hexahydrospiro[1,3-dioxolane-2,6'(2'H)-quinolein]-2'-one | 372955-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (4R',4a'S)-(-)-4',4a'-dimethyl-1'-[(1R)-1-phenylethyl]-1',3',4',4a',5',7'-hexahydrospiro[1,3-dioxolane-2,6'(2'H)-quinolein]-2'-one
• 英文别名: (4'R,4'aS)-4',4'a-dimethyl-1'-[(1R)-1-phenylethyl]spiro[1,3-dioxolane-2,6'-3,4,5,7-tetrahydroquinoline]-2'-one
• CAS: 372955-66-3
• 化学式: C₂₁H₂₇NO₃
• 分子量: 341.45
• InChiKey: ZYLYSPHCFUHKSL-QINHECLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R',4a'S)-(-)-4',4a'-dimethyl-1'-[(1R)-1-phenylethyl]-1',3',4',4a',5',7'-hexahydrospiro[1,3-dioxolane-2,6'(2'H)-quinolein]-2'-one 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以86%的产率得到(4R',4a'S)-(-)-4',4a'-dimethyl-1',3',4',4a',5',7'-hexahydrospiro[1,3-dioxolane-2,6'(2'H)-quinolein]-2'-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
• 作为产物：
  描述：

  7-甲基-1,4-二氧杂-螺[4.5]癸烷-8-酮 在 对苯二酚 作用下， 以 甲苯 为溶剂， 反应 184.0h， 生成 (4R',4a'S)-(-)-4',4a'-dimethyl-1'-[(1R)-1-phenylethyl]-1',3',4',4a',5',7'-hexahydrospiro[1,3-dioxolane-2,6'(2'H)-quinolein]-2'-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.