(-)-(SS,5a'S,8a'R)-9'-[(4-methylphenyl)sulfinyl]-1',5a',6',7',8',8a'-hexahydro-5'H-spiro[cyclohexane-1,3'-cyclopenta[d][1,3]oxazolo[3,4-a]pyridin]-5'-one | 875150-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (-)-(SS,5a'S,8a'R)-9'-[(4-methylphenyl)sulfinyl]-1',5a',6',7',8',8a'-hexahydro-5'H-spiro[cyclohexane-1,3'-cyclopenta[d][1,3]oxazolo[3,4-a]pyridin]-5'-one
• 英文别名: (-)-(S_S,5a'S,8a'R)-9'-[(4-methylphenyl)sulfinyl]-1',5a',6',7',8',8a'-hexahydro-5'H-spiro[cyclohexane-1,3'-cyclopenta[d][1,3]oxazolo[3,4-a]pyridin]-5'-one
• CAS: 875150-89-3
• 化学式: C₂₂H₂₇NO₃S
• 分子量: 385.527
• InChiKey: XQKZNLLBADQYOC-UHMYUZELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  27.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (-)-(SS,5a'S,8a'R)-9'-[(4-methylphenyl)sulfinyl]-1',5a',6',7',8',8a'-hexahydro-5'H-spiro[cyclohexane-1,3'-cyclopenta[d][1,3]oxazolo[3,4-a]pyridin]-5'-one 在 镍 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以97%的产率得到(+)-(5aS,8aS,9aS)-octahydro-5'H-spiro[cyclohexane-1,3'-cyclopenta[d][1,3]oxazolo[3,4-a]pyridin]-5'-one
  参考文献：
  名称：

  Diastereoselective synthesis of 3,4-disubstituted 5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones: chirality transfer in the enantioselective synthesis of ethyl (+)-(3S,4aS,7aS)-1-oxo-octahydro-1H-cyclopenta[c]pyridine-3-carboxylate

  摘要：

  The base-mediated reaction of enantiomerically pure alpha-sulfinylketimine (+)-1 with (E)-alpha,beta-disubstituted propenoate esters afforded 3,4-disubstituted-5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones 9 alpha-13 alpha and 14 with high or complete diastereoselectivity. A sole diastereomer of the four possible ones, with regard to the nature of ester, was isolated, which revealed the stereocontrol of the chiral sulfinyl group in the Michael reaction and transenolization steps. In addition, the enantioselective synthesis of ethyl (+)(3S,4aS,7aS)-1-oxo-octahydro-H-1-cyclopenta[c]pyridine-3-carboxylates (+)-17 alpha is described (five steps; 47% yield; ee >= 97%). The absolute configuration of stereocentres introduced in (+)-17 alpha was assigned on the basis of H-1 NMR data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.009
• 作为产物：
  描述：

  1-环戊烯-1-甲酸乙酯 、 (R)-2,2-pentamethylene-4-(p-tolylsulfinyl)methyl-2,5-dihydroixazole 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 168.0h， 以83%的产率得到(-)-(SS,5a'S,8a'R)-9'-[(4-methylphenyl)sulfinyl]-1',5a',6',7',8',8a'-hexahydro-5'H-spiro[cyclohexane-1,3'-cyclopenta[d][1,3]oxazolo[3,4-a]pyridin]-5'-one
  参考文献：
  名称：

  Diastereoselective synthesis of 3,4-disubstituted 5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones: chirality transfer in the enantioselective synthesis of ethyl (+)-(3S,4aS,7aS)-1-oxo-octahydro-1H-cyclopenta[c]pyridine-3-carboxylate

  摘要：

  The base-mediated reaction of enantiomerically pure alpha-sulfinylketimine (+)-1 with (E)-alpha,beta-disubstituted propenoate esters afforded 3,4-disubstituted-5-(p-tolylsulfinyl)-5,6-dehydropiperidin-2-ones 9 alpha-13 alpha and 14 with high or complete diastereoselectivity. A sole diastereomer of the four possible ones, with regard to the nature of ester, was isolated, which revealed the stereocontrol of the chiral sulfinyl group in the Michael reaction and transenolization steps. In addition, the enantioselective synthesis of ethyl (+)(3S,4aS,7aS)-1-oxo-octahydro-H-1-cyclopenta[c]pyridine-3-carboxylates (+)-17 alpha is described (five steps; 47% yield; ee >= 97%). The absolute configuration of stereocentres introduced in (+)-17 alpha was assigned on the basis of H-1 NMR data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.11.009