diethyl (2S,5R)-2,5-bis(benzylsulfanyl)-1,4-dimethyl-3,6-dioxopiperazine-2,5-dicarboxylate | 1215725-20-4

• 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: diethyl (2S,5R)-2,5-bis(benzylsulfanyl)-1,4-dimethyl-3,6-dioxopiperazine-2,5-dicarboxylate
• CAS: 1215725-20-4
• 化学式: C₂₆H₃₀N₂O₆S₂
• 分子量: 530.666
• InChiKey: DXFOPFUURCJTOG-WMPKNSHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-(benzylsulfanyl)-1,2,4-triazole 、 diethyl 1,4-dimethyl-3,6-dioxopiperazine-2,5-dicarboxylate 在 hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以72%的产率得到diethyl (2S,5R)-2,5-bis(benzylsulfanyl)-1,4-dimethyl-3,6-dioxopiperazine-2,5-dicarboxylate
  参考文献：
  名称：

  Enantioselective organocatalytic α-sulfenylation of substituted diketopiperazines

  摘要：

  The asymmetric organocatalytic alpha-sulfenylation of substituted piperazine-2,5-diones is reported, with cinchona alkaloids as chiral Lewis bases and electrophilic sulfur transfer reagents. Catalyst loadings, the type of sulfur transfer reagent, temperature and solvent were investigated in order to optimize the reaction conditions. The effects of ring substitution and the type of catalyst on the yield and enantioselectivity of the reaction are reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.037

文献信息

• Enantioselective organocatalytic α-sulfenylation of substituted diketopiperazines
  作者：Nathan W. Polaske、Ramin Dubey、Gary S. Nichol、Bogdan Olenyuk

  DOI：10.1016/j.tetasy.2009.10.037

  日期：2009.12

  The asymmetric organocatalytic alpha-sulfenylation of substituted piperazine-2,5-diones is reported, with cinchona alkaloids as chiral Lewis bases and electrophilic sulfur transfer reagents. Catalyst loadings, the type of sulfur transfer reagent, temperature and solvent were investigated in order to optimize the reaction conditions. The effects of ring substitution and the type of catalyst on the yield and enantioselectivity of the reaction are reported. (C) 2009 Elsevier Ltd. All rights reserved.