(3R,4R)-3-(benzylideneamino)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-[(1S)-1-(4-methoxyphenyl)ethyl]-3-methylpyrrolidin-2-one | 1192132-54-9

• 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: (3R,4R)-3-(benzylideneamino)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-[(1S)-1-(4-methoxyphenyl)ethyl]-3-methylpyrrolidin-2-one
• CAS: 1192132-54-9
• 化学式: C₂₈H₄₀N₂O₃Si
• 分子量: 480.723
• InChiKey: CMUOHTFEFZPLAD-YGZVCBRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-(benzylideneamino)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-[(1S)-1-(4-methoxyphenyl)ethyl]-3-methylpyrrolidin-2-one 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以76%的产率得到(3R,4R,1'S)-3-amino-4-hydroxymethyl-1-[1'-(4-methoxyphenyl)ethyl]-3-methylpyrrolidin-2-one
  参考文献：
  名称：

  New isosteres of (R)-2-methylhomoserine and (R)-2-methylaspartic acid by alkylation of a chiral imine leading stereoselectively to a quaternary stereogenic center

  摘要：

  Imines obtained from either chiral 3-amino-4-silyloxymethylpyrrolidin-2-one 5a or 5b underwent alkylation to give, in good yield and total stereoselection, the corresponding 3,3,4-trisubstituted pyrrolidin-2-ones 8a-d where both the amino and the silyloxymethyl groups lie cis to each other, as shown by H-1 NMR spectroscopic data and NOE experiments. By removal of both the imino group and the chiral inducer from 8b, the pyrrolidin-2-one 12, an isostere of(R)-2-methylhomoserine 2 and the pyrrolidin-2-one 14, an isostere of (R)-2-methylaspartic acid 4 were obtained straightforwardly. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.005
• 作为产物：
  描述：

  (3S,4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1-[(1S)-1-(4-methoxyphenyl)ethyl]-3-{[phenylmethylene]amino}pyrrolidin-2-one 、 碘甲烷 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以78%的产率得到(3R,4R)-3-(benzylideneamino)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-[(1S)-1-(4-methoxyphenyl)ethyl]-3-methylpyrrolidin-2-one
  参考文献：
  名称：

  New isosteres of (R)-2-methylhomoserine and (R)-2-methylaspartic acid by alkylation of a chiral imine leading stereoselectively to a quaternary stereogenic center

  摘要：

  Imines obtained from either chiral 3-amino-4-silyloxymethylpyrrolidin-2-one 5a or 5b underwent alkylation to give, in good yield and total stereoselection, the corresponding 3,3,4-trisubstituted pyrrolidin-2-ones 8a-d where both the amino and the silyloxymethyl groups lie cis to each other, as shown by H-1 NMR spectroscopic data and NOE experiments. By removal of both the imino group and the chiral inducer from 8b, the pyrrolidin-2-one 12, an isostere of(R)-2-methylhomoserine 2 and the pyrrolidin-2-one 14, an isostere of (R)-2-methylaspartic acid 4 were obtained straightforwardly. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.005

文献信息

• New isosteres of (R)-2-methylhomoserine and (R)-2-methylaspartic acid by alkylation of a chiral imine leading stereoselectively to a quaternary stereogenic center
  作者：Emanuela Crucianelli、Gianluca Martelli、Mario Orena、Samuele Rinaldi、Federica Sgolastra

  DOI：10.1016/j.tetasy.2009.07.005

  日期：2009.8

  Imines obtained from either chiral 3-amino-4-silyloxymethylpyrrolidin-2-one 5a or 5b underwent alkylation to give, in good yield and total stereoselection, the corresponding 3,3,4-trisubstituted pyrrolidin-2-ones 8a-d where both the amino and the silyloxymethyl groups lie cis to each other, as shown by H-1 NMR spectroscopic data and NOE experiments. By removal of both the imino group and the chiral inducer from 8b, the pyrrolidin-2-one 12, an isostere of(R)-2-methylhomoserine 2 and the pyrrolidin-2-one 14, an isostere of (R)-2-methylaspartic acid 4 were obtained straightforwardly. (c) 2009 Elsevier Ltd. All rights reserved.