rel-(3R,4S)-3-[(1R)-1-羟乙基]-1,4-二苯基-2-氮杂环丁酮 | 87342-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: rel-(3R,4S)-3-[(1R)-1-羟乙基]-1,4-二苯基-2-氮杂环丁酮
• 英文名称: αR_*-cis-3-(1-hydroxy-ethyl)-1,4-diphenyl-2-azetidinone
• 英文别名: (3R,4S)-3-[(1S)-1-hydroxyethyl]-1,4-diphenylazetidin-2-one
• CAS: 87342-69-6；87392-82-3；87419-59-8；93712-37-9；93712-38-0；93712-39-1；93712-40-4；100349-05-1；106399-66-0；106399-68-2；106399-69-3；106399-71-7；106400-00-4；113830-80-1
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: SZILNLKXIXTFEP-VBNZEHGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Formic acid (R)-1-((3S,4S)-2-oxo-1,4-diphenyl-azetidin-3-yl)-ethyl ester 在 水 作用下， 生成 rel-(3R,4S)-3-[(1R)-1-羟乙基]-1,4-二苯基-2-氮杂环丁酮
  参考文献：
  名称：

  Stereoselective synthesis of 3-(1-Hydroxyethyl)-2-azetidinonesfrom 3-hydroxybutyrates

  摘要：

  DOI：

  10.1016/s0040-4039(01)91165-7

文献信息

• Synthesis of N,4-diaryl substituted ?-lactams via Kinugasa cycloaddition/rearrangement reaction
  作者：Micha Michalak、Maciej Stodulski、Sebastian Stecko、Magdalena Wonica、Olga Staszewska-Krajewska、Przemysaw Kalicki、Bartomiej Furman、Jadwiga Frelek、Marek Chmielewski

  DOI：10.1016/j.tet.2011.11.007

  日期：2012.12

  substituted β-lactam framework, based on the Kinugasa cycloaddition/rearrangement sequence is presented. The series of protected chiral propargyl alcohols was treated with diaryl nitrones to afford mainly the cis-I adduct, providing direct access to the highly-functionalized azetitidin-2-one derivatives with a well-defined stereochemistry. Under the optimized reaction conditions, the unprotected chiral propargylic

  提出了基于Kinugasa环加成/重排序列的N，4-二芳基取代的β-内酰胺骨架的构建方法。该系列受保护的手性炔丙基醇中的溶液用碳酸二芳基硝酮主要得到处理的顺-我加成物，提供具有良好限定的立体化学可直接进入高度官能azetitidin -2-酮衍生物。在优化的反应条件下，还发现未保护的手性炔丙基醇是β-内酰胺的合适前体。通过CD或HPLC-CD技术确定加合物的绝对构型，这被证明是确定4-芳基取代的氮杂环丁烷-2-酮在C-4处构型的可靠方法。在差向异构顺通过将四元β-内酰胺环旁边的羟基氧化成酮，然后进行丙二酰片段的碱介导的差向异构化，可以容易地完成各个反式异构体的加合物。
• A stereocontrolled synthesis of 3-(1′-hydroxyethyl)-2-azetidinones through trimethylsilyl trifluoromethanesulphonate catalyzed condensation of silyl ketene acetal derived from ethyl 3-hydroxybutyrate and imine
  作者：Giuseppe Guanti、Enrica Narisano、Luca Banfi

  DOI：10.1016/s0040-4039(00)96502-x

  日期：1987.1

  The silyl ketene acetal 2, prepared from ethyl 3-hydroxybutyrate, reacted with benzylidene aniline in the presence of trimethylsilyl trifluoromethanesulphonate to furnish in satisfactory yield the β-amino ester 3 as a single diastereomer, which was subsequentially cyclized to the corresponding β-lactam.

  由3-羟基丁酸乙酯制备的甲硅烷基乙烯酮缩醛2在三甲基甲硅烷基三氟甲磺酸酯的存在下与亚苄基苯胺反应，以令人满意的产率提供作为单一非对映异构体的β-氨基酯3，随后将其环化为相应的β-内酰胺。
• Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives
  作者：Masahiro Miura、Masahiro Enna、Kazumi Okuro、Masakatsu Nomura

  DOI：10.1021/jo00121a018

  日期：1995.8

  Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza- 1-buten-3-ynes in good yields. In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products. The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used. Asymmetric induction is also observed in the reaction of phenylacetylene with alpha,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.
• Stereoselective synthesis of 3-(1-Hydroxyethyl)-2-azetidinonesfrom 3-hydroxybutyrates
  作者：Gunda I. Georg

  DOI：10.1016/s0040-4039(01)91165-7

  日期：1984.1