(6R,8S,8aS)-6-methyl-8-(p-toluenesulfonyl)perhydro-3,7-indolizidinedione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6R,8S,8aS)-6-methyl-8-(p-toluenesulfonyl)perhydro-3,7-indolizidinedione
• 英文别名: (6R,8S,8aS)-6-methyl-8-(4-methylphenyl)sulfonyl-1,2,5,6,8,8a-hexahydroindolizine-3,7-dione
• 化学式: C₁₆H₁₉NO₄S
• 分子量: 321.397
• InChiKey: FGUCGHWYGZAKJG-FFSVYQOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-(+)-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯 在 Oxone 、 sodium hydroxide 、 sodium hydride 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 40.0h， 生成 (6R,8S,8aS)-6-methyl-8-(p-toluenesulfonyl)perhydro-3,7-indolizidinedione
  参考文献：
  名称：

  Convergent asymmetric synthesis of indolizidines from (S)-5-(tosylmethyl)-2-pyrrolidinone: synthesis of (−)-δ-coniceine

  摘要：

  The enantiomerically pure (S)-5-(tosylmethyl)-2-pyrrolidinone 2, prepared from commercially available (S)-pyroglutaminol, is dialkylated at the nitrogen atom and the cc-sulfonyl position using several dielectrophiles using sodium hydride as the base to diastereoselectively afford indolizidine derivatives 5 and the less common hexahydropyrrolo[1,2-a]azepin-3-one 6 in moderate to good yield. This domino process has been applied to the synthesis of (-)-delta -coniceine. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00377-9

文献信息

• (E)-5-tosyl-4-pentenamide: A vinyl sulfone for the one-pot general synthesis of indolizidine derivatives
  作者：Francisco Caturla、Carmen Nájera

  DOI：10.1016/s0040-4039(97)00736-3

  日期：1997.5

  (E)-5-tosyl-4-pentenamide (3), easily prepared from 4-pentenoic acid by stereoselective iodosulfonylation-dehydroiodination and further amidation with oxalyl chloride and ammonia, reacts with sodium hydride at room temperature in DMF and then with 1,3-dielectrophiles such as 1,3-dihalides and alpha,beta-unsaturated esters to provide stereoselectively differently substituted indolizidines 6. (C) 1997 Elsevier Science Ltd.

  (E)-5-tosyl-4-pentenamide（3）是一种通过立体选择性碘砜化-脱碘化使4-烯酸酸酐（4-pentenoic acid）合成的，随后用氧化氯（oxalyl chloride）和氨（ammonia）进行进一步的 amidation反 应， 可 以 得 到。该化合物在DMF中与 NaH 在 室温下反应，随后与1,3-二价电位化合物（如1,3-双卤代物和α,β-不饱和酯）反应，可 以 产 生具 有 不 同 引物选择性取代位的标注6的立体 indolizidines。（C）1997 Elsevier Science Ltd.
• Convergent asymmetric synthesis of indolizidines from (S)-5-(tosylmethyl)-2-pyrrolidinone: synthesis of (−)-δ-coniceine
  作者：Ana Costa、Carmen Nájera、José M. Sansano

  DOI：10.1016/s0957-4166(01)00377-9

  日期：2001.8

  The enantiomerically pure (S)-5-(tosylmethyl)-2-pyrrolidinone 2, prepared from commercially available (S)-pyroglutaminol, is dialkylated at the nitrogen atom and the cc-sulfonyl position using several dielectrophiles using sodium hydride as the base to diastereoselectively afford indolizidine derivatives 5 and the less common hexahydropyrrolo[1,2-a]azepin-3-one 6 in moderate to good yield. This domino process has been applied to the synthesis of (-)-delta -coniceine. (C) 2001 Elsevier Science Ltd. All rights reserved.