methyl 4-[oxido(triisopropylsiloxy)imino]butanoate | 1181217-73-1

• 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 4-[oxido(triisopropylsiloxy)imino]butanoate
• CAS: 1181217-73-1
• 化学式: C₁₄H₂₉NO₄Si
• 分子量: 303.474
• InChiKey: PLNSMUFRCMPPEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  61.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 4-[oxido(triisopropylsiloxy)imino]butanoate 在 sodium tetrahydroborate 、 copper(II) bis(trifluoromethanesulfonate) 、 S-4,5-二氢-2-(2-((S)-4,5-二氢-4-异丙基噁唑-2-基)丙-2-基)-4-异丙基噁唑 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-[(3S,4R,5R)-4-methoxycarbonyl-3-(2-methoxycarbonylethyl)-N-triisopropylsilyloxy-2-isoxazolidin-5-yl]methanol
  参考文献：
  名称：

  Silyl Nitronate Cycloadditions Catalyzed by Cu(II)-Bisoxazoline

  摘要：

  Cu(OTf)(2) and chiral BOX ligand-catalyzed 1,3-dipolar cydoadditions Of triisopropylsilyl nitronates with alpha,beta-unsaturated carboximides produced chiral isoxazolines in high yields, high enantioselectivities, and complete diastereoselectivities. These chiral isoxazoline products were further converted into structurally diversified derivatives, which demonstrated the utility of the new method of constructing isoxazolines. The transition-state structure of cydoaddition was proposed in the light of the relative and absolute configurations of the products.

  DOI：

  10.1021/acs.joc.5b02035
• 作为产物：
  描述：

  三异丙基氯硅烷 、 4-硝基丁酸甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 4-[oxido(triisopropylsiloxy)imino]butanoate
  参考文献：
  名称：

  Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis

  摘要：

  The first enantioselective organocatalytic alpha-nitroatkylation of aldehydes has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl. nitronate to produce a beta-nitroaldehyde. Two methods, one that furnishes the syn beta-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-alpha,beta-disubstituted beta-amino acids is presented.

  DOI：

  10.1021/ja904504j