(3S,1'S)-3-(N-α-methylbenzyl-N'-benzylamino)-dodecanoate | 556068-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,1'S)-3-(N-α-methylbenzyl-N'-benzylamino)-dodecanoate
• 英文别名: ethyl (3S)-3-{benzyl[(1S)-1-phenylethyl]amino}dodecanoate；ethyl (3S)-3-[benzyl-[(1S)-1-phenylethyl]amino]dodecanoate
• CAS: 556068-55-4
• 化学式: C₂₉H₄₃NO₂
• 分子量: 437.666
• InChiKey: NSCQJALFOQIKPC-LSYYVWMOSA-N

物化性质

• 沸点：
  514.6±38.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,1'S)-3-(N-α-methylbenzyl-N'-benzylamino)-dodecanoate 在 palladium on activated charcoal 氢气 、 sodium 、 N,N-二异丙基乙胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~130.0 ℃ 、413.68 kPa 条件下， 生成 methyl (3S)-3-[(3S)-3-benzyl-2,5-dioxopiperazinyl]dodecanoate
  参考文献：
  名称：

  Determination of the absolute stereochemistry of Etzionin

  摘要：

  The absolute configuration of Etzionin, a marine peptide-like compound isolated in 1989 from a red tunicate collected from the Red Sea has been determined by a combination of synthetic and spectroscopic procedures. Finally, its absolute stereochemistry has been established as 3S,3'R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00403-8
• 作为产物：
  描述：

  癸醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 (3S,1'S)-3-(N-α-methylbenzyl-N'-benzylamino)-dodecanoate
  参考文献：
  名称：

  Determination of the absolute stereochemistry of Etzionin

  摘要：

  The absolute configuration of Etzionin, a marine peptide-like compound isolated in 1989 from a red tunicate collected from the Red Sea has been determined by a combination of synthetic and spectroscopic procedures. Finally, its absolute stereochemistry has been established as 3S,3'R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00403-8

文献信息

• A facile enantioselective synthesis of 2-(2-aminoethyl)allylsilanes, new synthons for piperidine synthesis
  作者：Jérémy Monfray、Yvonne Gelas-Mialhe、Jean-Claude Gramain、Roland Remuson

  DOI：10.1016/s0040-4039(03)01428-x

  日期：2003.7

  The synthesis of chiral (2-substituted-2-aminoethyl)allylsilanes by cerium mediated trimethylsilylmethylmagnesium chloride addition to the ester group of non racemic chiral β-aminoesters is described.

  描述了通过将铈介导的三甲基甲硅烷基甲基氯化镁加到非外消旋手性β-氨基酯的酯基上来合成手性（2-取代的2-氨基乙基）烯丙基硅烷。
• A new asymmetric synthesis of 2,6-cis-disubstituted 4-methylenepiperidines: total synthesis of (+)-alkaloid 241D and (+)-isosolenopsin A
  作者：Jérémy Monfray、Yvonne Gelas-Mialhe、Jean-Claude Gramain、Roland Remuson

  DOI：10.1016/j.tetasy.2005.01.018

  日期：2005.3

  A highly diastereoselective synthesis of 2,6-cis-disubstituted-4-methylenepiperidines based on a Mannich type intramolecular cyclization of an allylsilane on an iminium ion is described. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of two natural piperidine alkaloids: (+)-alkaloid 241 D and (+)-isosolenopsin A. (C) 2005 Elsevier Ltd. All rights reserved.