methyl (5E)-5-[(R)-tert-butylsulfinyl]iminopentanoate | 1106776-93-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (5E)-5-[(R)-tert-butylsulfinyl]iminopentanoate
• CAS: 1106776-93-5
• 化学式: C₁₀H₁₉NO₃S
• 分子量: 233.332
• InChiKey: VVWNLAOXPFRGRT-KUCQQTCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (5E)-5-[(R)-tert-butylsulfinyl]iminopentanoate 、 2-环庚烯-1-酮 、 diethylzinc 在 chiral phosphoramidite ligand 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 正己烷 为溶剂， 反应 0.33h， 以85%的产率得到(R(S),2S,3S,1'R)-N-(tert-butylsulfinyl)-2-[1-amino-4-(methoxycarbonyl)butyl]-3-ethylcycloheptanone
  参考文献：
  名称：

  Tandem enantioselective conjugate addition–Mannich reactions: efficient multicomponent assembly of dialkylzincs, cyclic enones and chiral N-sulfinimines

  摘要：

  A convenient access to enantiopure beta-amino ketones through a multicomponent reaction of dialkyl zinc reagents, cyclic enones and chiral N-tert-butanesulfinimines is disclosed. Four diastereoisomers can be selectively obtained by the appropriate choice of the chiral ligand (L or ent-L) and the chiral N-sulfinimine (R-S or S-S). The protocol is particularly efficient when enolisable N-sulfinimines are used. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.076

文献信息

• Tandem enantioselective conjugate addition–Mannich reactions: efficient multicomponent assembly of dialkylzincs, cyclic enones and chiral N-sulfinimines
  作者：José C. González-Gómez、Francisco Foubelo、Miguel Yus

  DOI：10.1016/j.tetlet.2008.02.076

  日期：2008.4

  A convenient access to enantiopure beta-amino ketones through a multicomponent reaction of dialkyl zinc reagents, cyclic enones and chiral N-tert-butanesulfinimines is disclosed. Four diastereoisomers can be selectively obtained by the appropriate choice of the chiral ligand (L or ent-L) and the chiral N-sulfinimine (R-S or S-S). The protocol is particularly efficient when enolisable N-sulfinimines are used. (C) 2008 Elsevier Ltd. All rights reserved.