(R)-1,4-dibenzyl-3-phenylpiperazin-2-one | 1327310-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (R)-1,4-dibenzyl-3-phenylpiperazin-2-one
• 英文别名: 1,4-dibenzyl-(R)-3-phenyl-2-piperazinone
• CAS: 1327310-54-2
• 化学式: C₂₄H₂₄N₂O
• 分子量: 356.467
• InChiKey: NCNPFLWEJQVBBJ-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  alpha-溴苯乙酸 在 4-二甲氨基吡啶 、 四丁基碘化铵 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (S)-1,4-dibenzyl-3-phenylpiperazin-2-one 、 (R)-1,4-dibenzyl-3-phenylpiperazin-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

• Stereoselective Substitution of Configurationally Labile α-Bromo Aryl­acetates with Amines and Az­lactones by<scp>L</scp>-Threonine-Mediated Crystallization-Induced Dynamic Resolution
  作者：Yun Soo Choi、SeHee Park、Yong Sun Park

  DOI：10.1002/ejoc.201600201

  日期：2016.5

  We developed a highly stereoselective C–N and C–C bond-forming reaction by carrying out a crystallization-induced dynamic resolution (CIDR) of α-bromo arylacetates followed by a stereoselective substitution reaction with an amine or azlactone nucleophile. Applications of this synthetic method to the preparation of highly enantioenriched nitrogen-containing six-membered heterocycles and α,β-disubstituted

  我们通过对α-溴芳基乙酸酯进行结晶诱导动态拆分（CIDR），然后与胺或吖内酯亲核试剂进行立体选择性取代反应，开发了高度立体选择性的 C-N 和 C-C 键形成反应。还介绍了这种合成方法在制备高度对映体富集的含氮六元杂环和 α,β-二取代天冬氨酸中的应用。
• Asymmetric Synthesis of 3-Substituted Morpholinones and Piperazinones by L-Malate-mediated Dynamic Kinetic Resolution of α-Bromo Esters
  作者：Jin-Ho Baek、Jung-In Jang、Yong-Sun Park

  DOI：10.5012/bkcs.2011.32.11.4067

  日期：2011.11.20

  [e-mail] August 26, 2011, Accepted September 5, 2011Key Words : Dynamic kinetic resolution, Nucleophilic substitution, Malic acid, Chiral auxiliary, AsymmetricsynthesisChiral auxiliary-mediated dynamic resolution of α-haloesters has been known as an effective method for asym-metric synthesis of α-heteroatom substituted carboxylic acidderivatives.

  E-mail: [e-mail] August 26, 2011, Accepted September 5, 2011关键词：动态动力学拆分，亲核取代，苹果酸，手性助剂，不对称合成手性助剂介导的α-卤代酯动态拆分被称为不对称合成α-杂原子取代羧酸衍生物的有效方法。
• Asymmetric Catalytic Access to Piperazin-2-ones and Morpholin-2-ones in a One-Pot Approach: Rapid Synthesis of an Intermediate to Aprepitant
  作者：Sara Meninno、Alessandra Lattanzi

  DOI：10.1021/acs.joc.2c02491

  日期：——

  A one-pot Knoevenagel reaction/asymmetric epoxidation/domino ring-opening cyclization (DROC) has been developed from commercial aldehydes, (phenylsulfonyl)acetonitrile, cumyl hydroperoxide, 1,2-ethylendiamines, and 1,2-ethanol amines to provide 3-aryl/alkyl piperazin-2-ones and morpholin-2-ones in yields of 38 to 90% and up to 99% ee. Two out of the three steps are stereoselectively catalyzed by a

  一锅 Knoevenagel 反应/不对称环氧化/多米诺开环环化 (DROC) 是由商业醛、(苯磺酰基)乙腈、枯基氢过氧化物、1,2-乙二胺和 1,2-乙醇胺开发而成，可提供 3-芳基/烷基哌嗪-2-酮和吗啉-2-酮的产率为 38% 至 90%，ee 高达 99%。三个步骤中的两个是由奎宁衍生的尿素立体选择性催化的。该序列已应用于关键中间体的短对映选择性进入，以两种绝对构型参与强效止吐药阿瑞吡坦的合成。
• Asymmetric Epoxidation of Alkylidenemalononitriles: Key Step for One-Pot Approach to Enantioenriched 3-Substituted Piperazin-2-ones
  作者：Sara Meninno、Andreu Vidal-Albalat、Alessandra Lattanzi

  DOI：10.1021/acs.orglett.5b02186

  日期：2015.9.4

  The first enantioselective epoxidation of readily available alkylidenemalononitriles has been developed by using a multifunctional cinchona derived thiourea as the organocatalyst and cumyl hydroperoxide as the oxidant. A new simple one-pot asymmetric epoxidation/S(N)2 ring-opening reaction with 1,2-diamines leading to important enantioenriched heterocycles, i.e. 3-substituted piperazin-2-ones, has been established.
• 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.