methyl (RS)-5-(1',3'-dithian-2'-yl)cyclopent-1-enecarboxylate | 1046427-56-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: methyl (RS)-5-(1',3'-dithian-2'-yl)cyclopent-1-enecarboxylate
• CAS: 1046427-56-8
• 化学式: C₁₁H₁₆O₂S₂
• 分子量: 244.379
• InChiKey: NITDYPHZTQXEHI-UHFFFAOYSA-N

物化性质

• 沸点：
  360.6±42.0 °C(predicted)
• 密度：
  1.242±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (RS)-5-(1',3'-dithian-2'-yl)cyclopent-1-enecarboxylate 、 N-苄基异丙胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以53%的产率得到methyl (1RS,2SR,5SR)-2-(N-benzyl-N-isopropylamino)-5-(1',3'-dithian-2'-yl)cyclopentanecarboxylate
  参考文献：
  名称：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin

  摘要：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98% de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (I R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.016
• 作为产物：
  描述：

  1,3-二噻烷 、 methyl 5-acetoxy-cyclopentene-1-carboxylate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.5h， 以18%的产率得到methyl (RS)-5-(1',3'-dithian-2'-yl)cyclopent-1-enecarboxylate
  参考文献：
  名称：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate for the asymmetric synthesis of (1R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin

  摘要：

  Parallel kinetic resolution of methyl (RS)-5-tris(phenylthio)methyl-cyclopent-1-ene-carboxylate with a 50:50 pseudoenantiomeric mixture of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and lithium (R)N-3,4-dimethoxybenzyl-N-(alpha-methylbenzyl)amide provides an efficient entry to the corresponding homochiral methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tris(phenylthio)methyl-cyclopentane-carboxylate derivatives in >98% de, with subsequent, sequential desulfurisation with Raney Nickel, N-debenzylation and ester hydrolysis furnishing (I R,2S,5S)- and (1S,2R,5R)-5-methyl-cispentacin in high yield, >98% de and >98% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.05.016