[(S)-2-[(2S,6R)-1-methyl-6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethyl acetate] | 1125824-45-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(S)-2-[(2S,6R)-1-methyl-6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethyl acetate]
• 英文别名: (S)-2-[(2R,6S)-6-(2-acetyloxy-2-phenylethyl)-1-methylpiperidin-2-yl]-1-phenylethanone；(S)-2-[(2S,6R)-1-methyl-6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethyl acetate；(2R,6S,2′′S)-2′′-O-acetyl lobeline；(2R,6S,2"S)-2"-O-acetyllobeline；(2S,6S,2R)-2-[6-(2-Acetyloxy-2-phenylethyl)-1-methylpiperidin-2-yl]-1-phenylethanone hydrochloride；[(1S)-2-[(2S,6R)-1-methyl-6-phenacylpiperidin-2-yl]-1-phenylethyl] acetate
• CAS: 1125824-45-4
• 化学式: C₂₄H₂₉NO₃
• 分子量: 379.499
• InChiKey: GJWRCTSARJBEEU-GPXNEJASSA-N

物化性质

• 沸点：
  490.4±15.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(S)-2-[(2S,6R)-1-methyl-6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethyl acetate] 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 以43 mg的产率得到洛贝林
  参考文献：
  名称：

  Synthesis of (−)-lobeline via enzymatic desymmetrization of lobelanidine

  摘要：

  The bioactive alkaloid (-)-lobeline was synthesized via the stereoselective acylation (desymmetrization) of meso-lobelanidine by vinyl acetate in the presence of Candida antarctica lipase B. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.055
• 作为产物：
  描述：

  lobelanidine monoacetate 在 Jones reagent 作用下， 以 丙酮 为溶剂， 生成 [(S)-2-[(2S,6R)-1-methyl-6-(2-oxo-2-phenylethyl)piperidin-2-yl]-1-phenylethyl acetate]
  参考文献：
  名称：

  Synthesis of (−)-lobeline via enzymatic desymmetrization of lobelanidine

  摘要：

  The bioactive alkaloid (-)-lobeline was synthesized via the stereoselective acylation (desymmetrization) of meso-lobelanidine by vinyl acetate in the presence of Candida antarctica lipase B. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.055

文献信息

• Elucidating absolute configuration of unsaturated alcohols via enantioselective acylation reactions
  作者：Christina M. LeGay、Colton G. Boudreau、Darren J. Derksen

  DOI：10.1039/c3ob40709h

  日期：——

  Enantioselective nucleophilic acylation catalysis provides a simple method of determining absolute configuration for unsaturated alcohols. Extension of this technique to natural products and synthetic compounds, as well as current limitations of this approach, are also described.

  对映选择性核亲电酰化催化提供了一种简单的方法来确定不饱和醇的绝对构型。该技术在自然产品和合成化合物中的扩展以及该方法目前的局限性也进行了描述。
• Indirect Trapping of the Retroconjugate Addition Reaction Intermediate Involved in the Epimerization of Lobeline:  Application to the Synthesis of (−)-Sedamine
  作者：Guangrong Zheng、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1021/jo048848j

  日期：2004.11.1

  Alkyl chloroformates induced indirect trapping of the retroconjugate addition reaction intermediate involved in the epimerization of lobeline is described. This strategy was applied to the conversion of (−)-lobeline to (−)-sedamine in high overall yield.

  描述了烷基氯甲酸酯诱导的间接捕集参与lobeline差向异构化的逆向共轭加成反应中间体。将该策略应用于以高总收率将（-）-小叶碱转化为（-）-二胺。
• Synthesis of (−)-lobeline via enzymatic desymmetrization of lobelanidine
  作者：Robert Chênevert、Pierre Morin

  DOI：10.1016/j.bmc.2009.01.055

  日期：2009.3

  The bioactive alkaloid (-)-lobeline was synthesized via the stereoselective acylation (desymmetrization) of meso-lobelanidine by vinyl acetate in the presence of Candida antarctica lipase B. (C) 2009 Elsevier Ltd. All rights reserved.