(2R,6R,8S,12S)-1-aza-10-oxo-12-phenyl-4-thiatricyclo<6.4.0^1,8.0^2,6>dodecan-9-one | 147406-87-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,6R,8S,12S)-1-aza-10-oxo-12-phenyl-4-thiatricyclo<6.4.0^1,8.0^2,6>dodecan-9-one
• 英文别名: (2S,6R,8S,12S)-12-phenyl-10-oxa-4-thia-1-azatricyclo[6.4.0.02,6]dodecan-9-one
• CAS: 147406-87-9
• 化学式: C₁₅H₁₇NO₂S
• 分子量: 275.371
• InChiKey: FCCUURORSYONLB-IGQOVBAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,6R,8S,12S)-1-aza-10-oxo-12-phenyl-4-thiatricyclo<6.4.0^1,8.0^2,6>dodecan-9-one 在 palladium hydroxide - carbon 氢气 、 镍 、 三氟乙酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.0h， 生成 (2S,4R,5R)-4,5-dimethylproline
  参考文献：
  名称：

  Enantiocontrolled construction of bicyclic proline derivatives via one-pot generation and intramolecular trapping of chiral stabilised azomethine ylids

  摘要：

  Aldehydes possessing unsaturation at C-5 or C-6 condense with (5S)-phenylmorpholin-2-one (1), generating chiral stabilised azomethine ylids which undergo concommitant diastereospecific intramolecular 3+2 dipolar cycloaddition to furnish adducts (2), (4), and (5) which may be converted to homochiral bicyclic proline derivatives. Reductive desulfurisation of the thioether derivative (5) leads to (2S,4R,5R)-4,5-dimethylproline (7).

  DOI：

  10.1016/0040-4039(93)85121-c
• 作为产物：
  描述：

  allyl 2-hydroxyethyl sulfide 在 molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 (2R,6R,8S,12S)-1-aza-10-oxo-12-phenyl-4-thiatricyclo<6.4.0^1,8.0^2,6>dodecan-9-one
  参考文献：
  名称：

  Enantiocontrolled construction of bicyclic proline derivatives via one-pot generation and intramolecular trapping of chiral stabilised azomethine ylids

  摘要：

  Aldehydes possessing unsaturation at C-5 or C-6 condense with (5S)-phenylmorpholin-2-one (1), generating chiral stabilised azomethine ylids which undergo concommitant diastereospecific intramolecular 3+2 dipolar cycloaddition to furnish adducts (2), (4), and (5) which may be converted to homochiral bicyclic proline derivatives. Reductive desulfurisation of the thioether derivative (5) leads to (2S,4R,5R)-4,5-dimethylproline (7).

  DOI：

  10.1016/0040-4039(93)85121-c

文献信息

• Enantiocontrolled construction of bicyclic proline derivatives via one-pot generation and intramolecular trapping of chiral stabilised azomethine ylids
  作者：Laurence M. Harwood、Ian A. Lilley

  DOI：10.1016/0040-4039(93)85121-c

  日期：1993.1

  Aldehydes possessing unsaturation at C-5 or C-6 condense with (5S)-phenylmorpholin-2-one (1), generating chiral stabilised azomethine ylids which undergo concommitant diastereospecific intramolecular 3+2 dipolar cycloaddition to furnish adducts (2), (4), and (5) which may be converted to homochiral bicyclic proline derivatives. Reductive desulfurisation of the thioether derivative (5) leads to (2S,4R,5R)-4,5-dimethylproline (7).