9-benzyl 4-methyl (7RS)-7-(2-chloroacetylamino)-7,8-dihydro-3-methyl-6-oxo-2H,6H-pyrido[2,1-b][1,3]thiazine-4,9-dicarboxylate | 832111-37-2

• 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: 9-benzyl 4-methyl (7RS)-7-(2-chloroacetylamino)-7,8-dihydro-3-methyl-6-oxo-2H,6H-pyrido[2,1-b][1,3]thiazine-4,9-dicarboxylate
• 英文别名: 9-O-benzyl 4-O-methyl 7-[(2-chloroacetyl)amino]-3-methyl-6-oxo-7,8-dihydro-2H-pyrido[2,1-b][1,3]thiazine-4,9-dicarboxylate
• CAS: 832111-37-2
• 化学式: C₂₁H₂₁ClN₂O₆S
• 分子量: 464.927
• InChiKey: IXLWMGZBQJUKNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-benzyl 4-methyl (7RS)-7-(2-chloroacetylamino)-7,8-dihydro-3-methyl-6-oxo-2H,6H-pyrido[2,1-b][1,3]thiazine-4,9-dicarboxylate 在 邻苯二胺 作用下， 生成 9-benzyl 4-methyl (7RS)-7-amino-7,8-dihydro-3-methyl-6-oxo-2H,6H-pyrido[2,1-b][1,3]thiazine-4,9-dicarboxylate
  参考文献：
  名称：

  An interesting dichotomy in the cyclisation of exocyclic enamines with protected dehydroamino acids leading to different β-turn templates

  摘要：

  Two templates for the preparation of external beta-turns have been synthesised. In the course of the synthetic studies an interesting dichotomy was observed in the PCl3 catalysed reaction of exocyclic enamines such as 6 and 14 with protected dehydroamino acids. When amide protected dehydroamino acids were condensed with 6 and 14 the expected 6/6 and 6/5 fused bicyclic compounds such as 7 and 15 respectively were obtained, whereas when urethane protected dehydroamino acids were used, the 5/6 and 5/5 fused products 9 and 18 were obtained.(C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02141-x
• 作为产物：
  描述：

  2-[(2-氯乙酰基)氨基]丙-2-烯酸 、 methyl 2-benzyloxycarbonylmethylene-3,6-dihydro-5-methyl-2H-[1,3]-thiazine-4-carboxylate 在 三氯化磷 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 1.5h， 以68%的产率得到9-benzyl 4-methyl (7RS)-7-(2-chloroacetylamino)-7,8-dihydro-3-methyl-6-oxo-2H,6H-pyrido[2,1-b][1,3]thiazine-4,9-dicarboxylate
  参考文献：
  名称：

  Synthesis of external β-turn templates by reaction of protected dehydroamino acids with cyclic enaminoesters

  摘要：

  Two external beta-turn templates have been synthesised and one of them has been derivatised as a GLDV-tetrapeptide. In the course of the synthesis an interesting dichotomy was observed in the condensation of exocyclic enamines such as 4 and 19 with protected dehydroamino acids using phosphorus trichloride. When dehydroamido acids were condensed with the enamines 4 and 19 then 6/6 and 6/5 fused bicyclic compounds such as 5 and 20, respectively, were obtained, whereas, when dehydroamino acid urethanes were used, the 5/6 and 5/5 fused products 7 and 23 were obtained. The bicyclic template 20 was converted to the GLDV-tetrapeptide derivative 31 but the sensitivity to base of the acyl-enamine system of the template reduced the yield in the synthesis of the external turn 35. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.036

文献信息

• An interesting dichotomy in the cyclisation of exocyclic enamines with protected dehydroamino acids leading to different β-turn templates
  作者：Jane M. Berry、Paul M. Doyle、Douglas W. Young

  DOI：10.1016/s0040-4039(02)02141-x

  日期：2002.12

  Two templates for the preparation of external beta-turns have been synthesised. In the course of the synthetic studies an interesting dichotomy was observed in the PCl3 catalysed reaction of exocyclic enamines such as 6 and 14 with protected dehydroamino acids. When amide protected dehydroamino acids were condensed with 6 and 14 the expected 6/6 and 6/5 fused bicyclic compounds such as 7 and 15 respectively were obtained, whereas when urethane protected dehydroamino acids were used, the 5/6 and 5/5 fused products 9 and 18 were obtained.(C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of external β-turn templates by reaction of protected dehydroamino acids with cyclic enaminoesters
  作者：Jane M. Berry、Paul M. Doyle、Douglas W. Young

  DOI：10.1016/j.tet.2004.09.036

  日期：2005.1

  Two external beta-turn templates have been synthesised and one of them has been derivatised as a GLDV-tetrapeptide. In the course of the synthesis an interesting dichotomy was observed in the condensation of exocyclic enamines such as 4 and 19 with protected dehydroamino acids using phosphorus trichloride. When dehydroamido acids were condensed with the enamines 4 and 19 then 6/6 and 6/5 fused bicyclic compounds such as 5 and 20, respectively, were obtained, whereas, when dehydroamino acid urethanes were used, the 5/6 and 5/5 fused products 7 and 23 were obtained. The bicyclic template 20 was converted to the GLDV-tetrapeptide derivative 31 but the sensitivity to base of the acyl-enamine system of the template reduced the yield in the synthesis of the external turn 35. (C) 2004 Elsevier Ltd. All rights reserved.