(S)-1,4-dibenzyl-3-methylpiperazin-2-one | 1327310-76-8

• 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: (S)-1,4-dibenzyl-3-methylpiperazin-2-one
• 英文别名: 1,4-dibenzyl-(S)-3-methyl-2-piperazinone；(3S)-1,4-dibenzyl-3-methylpiperazin-2-one
• CAS: 1327310-76-8
• 化学式: C₁₉H₂₂N₂O
• 分子量: 294.396
• InChiKey: GVYRIAMGCSHJON-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  23.55
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N,N'-二苄基乙二胺 、 2-Bromo-propionic acid (R)-4,4-dimethyl-2-oxo-tetrahydro-furan-3-yl ester 在 四丁基碘化铵 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1,4-dibenzyl-(R)-3-methyl-2-piperazinone 、 (S)-1,4-dibenzyl-3-methylpiperazin-2-one
  参考文献：
  名称：

  动态拆分α-卤代手性酯，用于合成3-取代的哌嗪-2-酮

  摘要：

  在乙二胺亲核试剂的亲核取代中，已经研究了衍生自五种手性醇的α-卤代酯的动态拆分。α-卤代酯的立体选择性取代和自发环化后，可为不对称合成高达94：6 er的3-取代的哌嗪-2-酮提供实用的方案。

  DOI：

  10.1016/j.tet.2011.06.055

文献信息

• Enantioselective Organocatalytic Synthesis of 2-Oxopiperazines from Aldehydes: Identification of the Elusive Epoxy Lactone Intermediate
  作者：Nikolaos Kaplaneris、Constantinos Spyropoulos、Maroula G. Kokotou、Christoforos G. Kokotos

  DOI：10.1021/acs.orglett.6b02699

  日期：2016.11.18

  organocatalytic linchpin catalysis approach was envisaged to convert simple aldehydes into enantioenriched 2-oxopiperazines. A four-step reaction sequence (chlorination, oxidation, substitution, and cyclization) was developed and led to different substitution patterns in high yields and selectivities. The reaction mechanism was studied, and the previously elusive epoxy lactone intermediate was identified by

  设想了一种有机催化的关键催化方法，将简单的醛转化为对映体富集的2-氧代哌嗪。开发了四步反应序列（氯化，氧化，取代和环化），并以高收率和选择性导致了不同的取代方式。研究了反应机理，并通过HRMS鉴定了以前难以捉摸的环氧内酯中间体。
• A facile route for highly enantioenriched six‐membered 1,4‐<i>N,N</i>‐ and <i>N,O</i>‐heterocycles from <scp>L</scp>‐serinate‐derived <scp>α</scp>‐bromoacetates
  作者：So Jeong Lee、Min Ji Park、Seyeon Kim、Yong Sun Park

  DOI：10.1002/bkcs.12787

  日期：2023.12

  Preparation of highly enantioenriched six-membered 1,4-N,N- and N,O-heterocycles has been developed through [4 + 2] heteroannulation of α-bromoacetates with 1,4-binucleophiles. Two consecutive substitutions of highly diastereoenriched L-serinate-derived α-bromoacetates provide convenient access to a wide range of C-aryl/aliphatic substituted 1,4-N,N- and N,O-heterocycles with up to 99:1 er.

  通过 α-溴乙酸酯与 1,4-双亲核试剂的 [4 + 2] 杂环化，开发了高度对映体富集的六元 1,4- N,N-和N,O-杂环。高度非对映体富集的 L-丝氨酸衍生的 α-溴乙酸酯的两次连续取代可方便地获得各种 C-芳基/脂肪族取代的 1,4- N,N-和N,O-杂环，其比例高达 99:1。
• L-Tartaric Acid as a New Chiral Auxiliary for Asymmetric Synthesis of Piperazinones, Morpholinones, Dihydroquinoxalinones and Dihydrobenzoxazinones
  作者：Yelim Kim、Kon Ji Park、Yong Sun Park

  DOI：10.5012/bkcs.2012.33.11.3853

  日期：2012.11.20

  2012, Accepted August 10, 2012Key Words : Dynamic resolution, Nucleophilic substitution, Tartaric acid, Chiral auxiliary, Asymmetric syn-thesisDynamic resolution of α-haloacyl compounds in nucleo-philic substitution has been recently developed as an asym-metric synthetic method for α-substituted carboxylic acids.