(1S,2R)-N-methylephedrine acrylate | 187600-79-9

• 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: (1S,2R)-N-methylephedrine acrylate
• 英文别名: (1S,2R)-N-methylephedrinyl acrylate；[(1S,2R)-2-(dimethylamino)-1-phenylpropyl] prop-2-enoate
• CAS: 187600-79-9
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: SYNKPSQOFFOWAG-BXUZGUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (1S,2R)-N-methylephedrine acrylate 、 (Z)-N-(1-cyclohexylmethylidene)benzylamine-N-oxide 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以70%的产率得到4-(Benzyl-hydroxy-amino)-4-cyclohexyl-butyric acid (1S,2R)-2-dimethylamino-1-phenyl-propyl ester
  参考文献：
  名称：

  SmI（2）促进亚硝基向α，β-不饱和酰胺和酯的自由基加成反应：通过与酮基等同的氮原子合成γ-氨基酸。

  摘要：

  [反应：见正文]当烷基氮酮经相当于酮基自由基阴离子的氮与二碘化sa反应时，烷基硝酮会与一系列α，β-不饱和酰胺和酯发生自由基加成反应。该反应方便地提供了获得各种官能化的γ-氨基酸的途径。通过将硝酮自由基加成反应与具有手性助剂的丙烯酸酯/酰胺的反应，该方法扩展到了4-取代的γ-氨基酸的不对称合成。

  DOI：

  10.1021/ol027386y
• 作为产物：
  描述：

  (1S,2R)-(+)-N-methylephedrine 、 丙烯酰氯 生成 (1S,2R)-N-methylephedrine acrylate
  参考文献：
  名称：

  One-Step Highly Diastereoselective Synthesis of γ-Aminoalkyl-Substituted γ-Butyrolactones by an Asymmetric Samarium-Mediated Ketyl−Alkene Coupling Reaction

  摘要：

  The samarium(II) iodide mediated reaction of N,N-dibenzyl-protected (S)-alpha-amino aldehydes with (1S,2R)-N-methylephedrinyl acrylate gave the (4R,1'S)-gamma-(aminoalkyl)-gamma-butyrolactones in good yields with high diastereoselectivities (up to 80% de); (4R,1'S)-gamma-amino-(2-phenylethyl)-gamma-butyrolactone (6a), which should be a potent precursor for gamma-secretase inhibitors, was obtained with high de value.

  DOI：

  10.1021/jo020574h

文献信息

• One-Step Highly Diastereoselective Synthesis of γ-Aminoalkyl-Substituted γ-Butyrolactones by an Asymmetric Samarium-Mediated Ketyl−Alkene Coupling Reaction
  作者：Shin-ichi Fukuzawa、Manabu Miura、Takahide Saitoh

  DOI：10.1021/jo020574h

  日期：2003.3.1

  The samarium(II) iodide mediated reaction of N,N-dibenzyl-protected (S)-alpha-amino aldehydes with (1S,2R)-N-methylephedrinyl acrylate gave the (4R,1'S)-gamma-(aminoalkyl)-gamma-butyrolactones in good yields with high diastereoselectivities (up to 80% de); (4R,1'S)-gamma-amino-(2-phenylethyl)-gamma-butyrolactone (6a), which should be a potent precursor for gamma-secretase inhibitors, was obtained with high de value.
• A Facile Synthesis of Chiral γ-Butyrolactones in Extremely High Enantioselectivity Mediated by Samarium(II) Iodide
  作者：Shin-ichi Fukuzawa、Kazutaka Seki、Masahiro Tatsuzawa、Keisuke Mutoh

  DOI：10.1021/ja962965h

  日期：1997.2.1
• Total Synthesis of (−)-Spongidepsin
  作者：Laurent Ferrié,、Sébastien Reymond、Patrice Capdevielle、Janine Cossy

  DOI：10.1021/ol061029w

  日期：2006.8.1

  A convergent and rapid stereoselective synthesis of (-)-spongidepsin has been achieved from the Roche ester in 14 steps with an overall yield of 13%.
• SmI₂-Promoted Radical Addition of Nitrones to α,β-Unsaturated Amides and Esters:  Synthesis of γ-Amino Acids via a Nitrogen Equivalent to the Ketyl Radical
  作者：Ditte Riber、Troels Skrydstrup

  DOI：10.1021/ol027386y

  日期：2003.1.1

  [reaction: see text] Alkyl nitrones undergo radical addition reactions to a series of alpha,beta-unsaturated amides and esters when subjected to samarium diiodide via a nitrogen equivalent to a ketyl radical anion. This reaction conveniently provides access to a variety of functionalized gamma-amino acids. The methodology was extended to the asymmetric synthesis of 4-substituted gamma-amino acids,

  [反应：见正文]当烷基氮酮经相当于酮基自由基阴离子的氮与二碘化sa反应时，烷基硝酮会与一系列α，β-不饱和酰胺和酯发生自由基加成反应。该反应方便地提供了获得各种官能化的γ-氨基酸的途径。通过将硝酮自由基加成反应与具有手性助剂的丙烯酸酯/酰胺的反应，该方法扩展到了4-取代的γ-氨基酸的不对称合成。