1-(p-Anisyl)-4-furylazetidine-2,3-dione | 160947-56-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: 1-(p-Anisyl)-4-furylazetidine-2,3-dione
• 英文别名: 4-(2-furyl)-1-(4-methoxyphenyl)-2,3-azetidinedione；4-(furan-2-yl)-1-(4-methoxyphenyl)azetidine-2,3-dione；4-(2-Furanyl)-1-(4-methoxyphenyl)-2,3-azetidinedione
• CAS: 160947-56-8
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: NRKMGMXDZGGIRW-UHFFFAOYSA-N

物化性质

• 沸点：
  415.4±55.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  59.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(p-Anisyl)-4-furylazetidine-2,3-dione 在 sodium hydroxide 、 M₉ salt medium 葡萄糖 、 Escherichia coli BL₂₁(DE₃) 、 氧气 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 以40%的产率得到(3S,4R)-(+)-4-(furan-2-yl)-3-hydroxy-1-(4-methoxyphenyl)-2-azetidinone
  参考文献：
  名称：

  The dynamic kinetic resolution of 3-oxo-4-phenyl-β-lactam by recombinant E. coli overexpressing yeast reductase Ara1p

  摘要：

  Using a recombinant E coli strain overexpressing yeast reductase Ara 1 p, we reduced racemic 3-oxo-4-phenyl-beta-lactam to cis-(3S,4R)-3-hydroxy-4-phenyl-beta-lactam as a single enantiopure product. The dynamic kinetic resolution occurred over the course of fermentation at pH 7. Under the same conditions, 3-oxo-4-(2-thiophenyl)-beta-lactam 4 and 3-oxo-4-(2-furyl)-beta-lactam 5 were not resolved. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.029
• 作为产物：
  描述：

  1-(呋喃-2-基)-N-(4-甲氧基苯基)甲亚胺 在 四磷十氧化物 、 碳酸氢钠 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 1-(p-Anisyl)-4-furylazetidine-2,3-dione
  参考文献：
  名称：

  质子穿梭使镍催化的DKR催化α-酮基-β-内酰胺的不对称还原

  摘要：

  手性α-羟基-β-内酰胺是许多生物活性化合物和抗生素的关键片段，开发有效的合成方法具有重要价值。α-酮-β-内酰胺的高对映选择性动态动力学拆分（DKR）通过一种新颖的质子穿梭策略。Ni催化不对称氢化可有效地和对映选择性地还原各种α-酮-β-内酰胺，从而提供具有高收率和对映选择性的相应α-羟基-β-内酰胺衍生物（最高收率92％，最高收率94％ ee）。氘标记实验表明，苯基次膦酸通过促进烯醇化过程在α-酮-β-内酰胺的DKR中起关键作用。该方案的合成潜力通过其在紫杉酚和（+）- Epi -Cytoxazone关键中间体的合成中的应用得到证明。

  DOI：

  10.1039/d0cc05599a

文献信息

• Preparation of .alpha.-Methylene and .alpha.-Ethylidene .beta.-Lactams via the Ester Enolate-Imine Condensation Using .beta.-(Dialkylamino) Esters as Starting Materials: Scope and Synthetic Applications
  作者：Benito Alcaide、Gemma Esteban、Yolanda Martin-Cantalejo、Joaquin Plumet、Julian Rodriguez-Lopez、Angeles Monge、Virginia Perez-Garcia

  DOI：10.1021/jo00105a013

  日期：1994.12

  A new, simple procedure for the preparation of appropriately substituted alpha-methylene and alpha-ethylidene beta-lactams via the ester enolate-imine condensation is described. The method is based on the use of lithium 3-(dialkylamino) ester enolates as synthetic equivalents of the corresponding acrylate alpha-anions. Thus, the reaction of lithium enolates of 3-(dialkylamino) esters with imines produced alpha-[(dialkylamino)alkyl] beta-lactams stereoselectively and in high yield. Upon dehydroamination the latter furnished a variety of alpha-alkylidene beta-lactams. The synthesis of 3-alkylidene-4-formyl-2-azetidinones is a particularly significant feature of this work. Preparation of functionalized alpha-keto beta-lactams and beta-lactam-furan hybrids through a dihydroxylation-oxidation process starting from different alpha-alkylidene derivatives is also described. In addition, reduction of various 4-functionalized (Z)- and (E)-3-ethylidene-2-azetidinones yielded the corresponding 3-ethylideneazetidines as advanced precursors of polyoximic acids.
• Mihovilovic, Marko D.; Feicht, Anton; Kayser, Margaret M., Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 6, p. 585 - 590
  作者：Mihovilovic, Marko D.、Feicht, Anton、Kayser, Margaret M.

  DOI：——

  日期：——
• Ni-Catalyzed asymmetric reduction of α-keto-β-lactams <i>via</i> DKR enabled by proton shuttling
  作者：Fangyuan Wang、Xuefeng Tan、Ting Wu、Long-Sheng Zheng、Gen-Qiang Chen、Xumu Zhang

  DOI：10.1039/d0cc05599a

  日期：——

  Chiral α-hydroxy-β-lactams are key fragments of many bioactive compounds and antibiotics, and the development of efficient synthetic methods for these compounds is of great value. The highly enantioselective dynamic kinetic resolution (DKR) of α-keto-β-lactams was realized via a novel proton shuttling strategy. A wide range of α-keto-β-lactams were reduced efficiently and enantioselectively by Ni-catalyzed

  手性α-羟基-β-内酰胺是许多生物活性化合物和抗生素的关键片段，开发有效的合成方法具有重要价值。α-酮-β-内酰胺的高对映选择性动态动力学拆分（DKR）通过一种新颖的质子穿梭策略。Ni催化不对称氢化可有效地和对映选择性地还原各种α-酮-β-内酰胺，从而提供具有高收率和对映选择性的相应α-羟基-β-内酰胺衍生物（最高收率92％，最高收率94％ ee）。氘标记实验表明，苯基次膦酸通过促进烯醇化过程在α-酮-β-内酰胺的DKR中起关键作用。该方案的合成潜力通过其在紫杉酚和（+）- Epi -Cytoxazone关键中间体的合成中的应用得到证明。
• The dynamic kinetic resolution of 3-oxo-4-phenyl-β-lactam by recombinant E. coli overexpressing yeast reductase Ara1p
  作者：Yan Yang、Melissa Drolet、Margaret M. Kayser

  DOI：10.1016/j.tetasy.2005.07.029

  日期：2005.8

  Using a recombinant E coli strain overexpressing yeast reductase Ara 1 p, we reduced racemic 3-oxo-4-phenyl-beta-lactam to cis-(3S,4R)-3-hydroxy-4-phenyl-beta-lactam as a single enantiopure product. The dynamic kinetic resolution occurred over the course of fermentation at pH 7. Under the same conditions, 3-oxo-4-(2-thiophenyl)-beta-lactam 4 and 3-oxo-4-(2-furyl)-beta-lactam 5 were not resolved. (c) 2005 Elsevier Ltd. All rights reserved.