methyl [1-(1-(S)-phenylethyl)-piperidin-2-(R)-yl]acetate | 686343-39-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl [1-(1-(S)-phenylethyl)-piperidin-2-(R)-yl]acetate
• 英文别名: methyl 2-{(R)-1-[(S)-phenylethyl]piperidin-2-yl}acetate；methyl [(1S)-phenylethyl]-2(R)-piperidylacetate；methyl 2-[(2R)-1-[(1S)-1-phenylethyl]piperidin-2-yl]acetate
• CAS: 686343-39-5
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: QYRIDPZDHRVYKZ-DZGCQCFKSA-N

物化性质

• 沸点：
  332.6±15.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  methyl [1-(1-(S)-phenylethyl)-piperidin-2-(R)-yl]acetate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 40.0 ℃ 、300.0 kPa 条件下， 反应 6.0h， 以95%的产率得到甲基2-哌啶基乙酸酯
  参考文献：
  名称：

  (R)-高哌啶酸甲酯的方便多克合成

  摘要：

  (R)-高哌啶酸甲酯已由 3,4-二氢-2H-吡喃以 5 步和 36% 的总产率以多克规模制备。通过不对称迈克尔加成和分级结晶引入立体化学。

  DOI：

  10.1055/s-2006-926419
• 作为产物：
  描述：

  5-氯戊酸 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 四丁基碘化铵 、 三乙酰氧基硼氢化钠 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 33.0h， 生成 methyl [1-(1-(S)-phenylethyl)-piperidin-2-(R)-yl]acetate
  参考文献：
  名称：

  Practical method for the synthesis of (R)-homopipecolinic acid and (R)-homoproline esters from ω-chloroalkanoic acids and available chiral amines

  摘要：

  A practical synthesis of (R)-homopipecolinic acid methyl ester 1 and (R)-homoproline methyl ester 2 was performed utilizing (i) a direct intramolecular cyclization of omega-chloro-beta-enamino esters 11 and 12, which were prepared from available (S)-1-phenylethylamine or (S)-1-(1-naphthyl)ethylamine and omega-chloro-beta-keto esters 5 and 10, respectively and (ii) a highly diastereoselective NaBH4 reduction followed by hydrogenolysis. The present method is a short-step process using inexpensive and readily available substrates and reagents with fewer wasted materials. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.014

文献信息

• Novel Routes to Chiral 2-Alkoxy-5-/6- methoxycarbonylmethylidenepyrrolidines/-piperidines
  作者：Olivier David、Sandrine Calvet、François Chau、Corinne Vanucci-Bacqué、Marie-Claude Fargeau-Bellassoued、Gérard Lhommet

  DOI：10.1021/jo049961c

  日期：2004.4.1

  We report the results of a study aimed at the diastereoselective synthesis of chiral 2-alkoxy-5-/6-methoxy-carbonylmethylidenepyrrolidines/-piperidines by condensation of chiral amines onto omega-oxo alkynoates and omega-oxo beta-keto esters.
• Pereira, Jennifer; Calvet-Vitale, Sandrine; Fargeau-Bellassoued, Marie-Claude, Heterocycles, 2007, vol. 71, # 2, p. 437 - 444
  作者：Pereira, Jennifer、Calvet-Vitale, Sandrine、Fargeau-Bellassoued, Marie-Claude、Mouries-Mansuy, Virginie、Vanucci-Bacque, Corinne、Lhommet, Gerard

  DOI：——

  日期：——
• Practical method for the synthesis of (R)-homopipecolinic acid and (R)-homoproline esters from ω-chloroalkanoic acids and available chiral amines
  作者：Norio Hashimoto、Takashi Funatomi、Tomonori Misaki、Yoo Tanabe

  DOI：10.1016/j.tet.2005.12.014

  日期：2006.3

  A practical synthesis of (R)-homopipecolinic acid methyl ester 1 and (R)-homoproline methyl ester 2 was performed utilizing (i) a direct intramolecular cyclization of omega-chloro-beta-enamino esters 11 and 12, which were prepared from available (S)-1-phenylethylamine or (S)-1-(1-naphthyl)ethylamine and omega-chloro-beta-keto esters 5 and 10, respectively and (ii) a highly diastereoselective NaBH4 reduction followed by hydrogenolysis. The present method is a short-step process using inexpensive and readily available substrates and reagents with fewer wasted materials. (c) 2005 Elsevier Ltd. All rights reserved.
• Convenient Multigram Synthesis of (<i>R</i>)-Homopipecolic Acid Methyl Ester
  作者：Matthias Breuning、Melanie Steiner

  DOI：10.1055/s-2006-926419

  日期：2006.4

  (R)-Homopipecolic acid methyl ester has been prepared on a multigram scale from 3,4-dihydro-2H-pyran in five steps and 36% overall yield. The stereochemistry was introduced via an asymmetric Michael addition and a fractional crystallization.

  (R)-高哌啶酸甲酯已由 3,4-二氢-2H-吡喃以 5 步和 36% 的总产率以多克规模制备。通过不对称迈克尔加成和分级结晶引入立体化学。