7-azabicyclo[4.2.0]octan-8-one | 22031-53-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 7-azabicyclo[4.2.0]octan-8-one
• 英文别名: (1S,6R)-7-azabicyclo[4.2.0]octan-8-one
• CAS: 22031-53-4；34102-49-3；150781-24-1
• 化学式: C₇H₁₁NO
• mdl: MFCD19216947
• 分子量: 125.17
• InChiKey: SQHJLZVUXVHXKC-NTSWFWBYSA-N

物化性质

• 熔点：
  56-57 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  297.4±9.0 °C(Predicted)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-azabicyclo[4.2.0]octan-8-one 在 盐酸 作用下， 以 水 为溶剂， 反应 14.0h， 以92%的产率得到(1S,2R)-(+)-2-氢氯化氨基环己胺羧基酸
  参考文献：
  名称：

  Large-Scale Syntheses of FMOC-Protected Non-Proteogenic Amino Acids:  Useful Building Blocks for Combinatorial Libraries

  摘要：

  Convenient and reliable large-scale procedures for the protection of various amino acids with N-(9-fluorenyimethoxycarbonyl)oxysuccinimide (FMOC-OSu) are described. Commercially available 4-aminomethylbenzoic acid and trans-4-(aminomethyl)cyclohexanecarboxylic acid were converted into their corresponding FMOC-derivatives in excellent yields without the need for an extractive workup. In addition, FMOC-cis-beta -amino acids were also prepared, employing a [2 + 2]-cycloaddition strategy between a cyclic olefin and N-chlorosulfonyl isocyanate (CSI). The resulting N-chlorosulfonyl fl-lactams were reduced to the parent beta -lactams with sodium sulfite and then converted to the cis-fi-amino acid hydrochlorides by exposure to aqueous hydrochloric acid. The resulting cis-fi-amino acids were converted to their FMOC-derivatives under conditions similar to those developed for the commercially available amino acids. Differences in the conditions employed between these beta -amino acids and the commercial derivatives were observed, primarily in the nature of the base required for the reaction. A possible rationale for the differences in behavior is described. These FMOC-amino acid derivatives are valuable intermediates for the solid-phase synthesis of combinatorial libraries.

  DOI：

  10.1021/op010204f
• 作为产物：
  描述：

  (1S,6R)-8-oxo-7-azabicyclo[4.2.0]octane-7-sulfonyl chloride 在 水 、 sodium hydroxide 、 sodium sulfite 作用下， 生成 7-azabicyclo[4.2.0]octan-8-one
  参考文献：
  名称：

  Large-Scale Syntheses of FMOC-Protected Non-Proteogenic Amino Acids:  Useful Building Blocks for Combinatorial Libraries

  摘要：

  Convenient and reliable large-scale procedures for the protection of various amino acids with N-(9-fluorenyimethoxycarbonyl)oxysuccinimide (FMOC-OSu) are described. Commercially available 4-aminomethylbenzoic acid and trans-4-(aminomethyl)cyclohexanecarboxylic acid were converted into their corresponding FMOC-derivatives in excellent yields without the need for an extractive workup. In addition, FMOC-cis-beta -amino acids were also prepared, employing a [2 + 2]-cycloaddition strategy between a cyclic olefin and N-chlorosulfonyl isocyanate (CSI). The resulting N-chlorosulfonyl fl-lactams were reduced to the parent beta -lactams with sodium sulfite and then converted to the cis-fi-amino acid hydrochlorides by exposure to aqueous hydrochloric acid. The resulting cis-fi-amino acids were converted to their FMOC-derivatives under conditions similar to those developed for the commercially available amino acids. Differences in the conditions employed between these beta -amino acids and the commercial derivatives were observed, primarily in the nature of the base required for the reaction. A possible rationale for the differences in behavior is described. These FMOC-amino acid derivatives are valuable intermediates for the solid-phase synthesis of combinatorial libraries.

  DOI：

  10.1021/op010204f

文献信息

• Enantiomeric discrimination of cyclic β-amino acids using (18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent
  作者：Cora D. Chisholm、Ferenc Fülöp、Eniko Forró、Thomas J. Wenzel

  DOI：10.1016/j.tetasy.2010.07.031

  日期：2010.9

  (18-Crown-6)-2,3,11,12-tetracarboxylic acid is an excellent chiral NMR solvating agent for cyclic β-amino acids with cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, bicyclo[2.2.1]heptane, and bicyclo[2.2.1]heptene rings. The crown ether was added to the neutral β-amino acids in methanol-d4. A neutralization reaction between the crown ether and β-amino acid forms the ammonium ion needed for

  （18-Crown-6）-2,3,11,12-四羧酸是一种出色的手性NMR溶剂，用于环β-氨基酸与环戊烷，环己烷，环庚烷，环戊烯，环己烯，双环[2.2.1]庚烷，和双环[2.2.1]庚烯环。将冠醚加入到甲醇-d 4中的中性β-氨基酸中。冠醚和β-氨基酸之间的中和反应形成有利缔合所需的铵离子。在所研究的每种底物上均观察到两个氢原子α与β-氨基酸的胺和羧酸部分的对映体区别。对于相似结构的底物，某些氢原子的对映异构顺序的变化趋势与绝对构型相关。
• β-Lactams as Formal Dipoles through Amide-Bond Activation
  作者：Vincent Barbier、Jérôme Marrot、François Couty、Olivier R. P. David

  DOI：10.1002/ejoc.201501342

  日期：2016.1

  Activation of β-lactams can be achieved by simple Lewis-base catalysis to trigger an unprecedented reaction based on the formal dipolar behaviour of a strained amide bond. A new synthetic route for 1,3-oxazinan-6-ones is presented by reaction of β-lactams with ethylglyoxylate, which after methodological optimizations identified 4-pyrrolidinopyridine as the catalyst of choice in aprotic polar solvents

  β-内酰胺的活化可以通过简单的路易斯碱催化来实现，以基于张力酰胺键的形式偶极行为触发前所未有的反应。β-内酰胺类与乙醛酸乙酯反应，提出了一种新的 1,3-恶嗪喃-6-酮合成路线，经过方法优化后确定 4-吡咯烷基吡啶为非质子极性溶剂中的首选催化剂。还根据为这种转变确定的内在局限性讨论了机械细节。
• Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane β-Amino Acid Derivatives
  作者：Loránd Kiss、Enikő Forró、György Orsy、Renáta Ábrahámi、Ferenc Fülöp

  DOI：10.3390/molecules201219749

  日期：——

  Cyclohexane analogues of the antifungal icofungipen [(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid] were selectively synthesized from unsaturated bicyclic β-lactams by transformation of the ring olefinic bond through three different regio- and stereocontrolled hydroxylation techniques, followed by hydroxy group oxidation and oxo-methylene interconversion with a phosphorane. Starting from an

  通过三种不同的区域和立体控制羟基化技术，通过环烯烃键的转化，从不饱和双环β-内酰胺选择性地合成了抗真菌剂icofungipen [（1R，2S）-2-氨基-4-亚甲基环戊烷羧酸]的环己烷类似物羟基氧化和氧代亚甲基与磷烷的相互转化。从通过消旋外消旋化合物的酶促拆分获得的对映体纯的双环β-内酰胺开始，对映发散的方法导致制备了艾可芬净的右旋和左旋环己烷类似物。
• Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis
  作者：Sayeh Shahmohammadi、Tünde Faragó、Márta Palkó、Enikő Forró

  DOI：10.3390/molecules27082600

  日期：——

  Candida antarctica lipase B-catalyzed hydrolysis of carbocyclic 5–8-membered cis β-amino esters was carried out in green organic media, under solvent-free and ball-milling conditions. In accordance with the high enantioselectivity factor (E > 200) observed in organic media, the preparative-scale resolutions of β-amino esters were performed in tBuOMe at 65 °C. The unreacted β-amino ester enantiomers

  在无溶剂和球磨条件下，在绿色有机介质中进行了南极假丝酵母脂肪酶 B 催化的碳环5-8 元顺式 β-氨基酯水解。根据在有机介质中观察到的高对映选择性因子 ( E > 200)，β-氨基酯的制备级拆分是在 65 °C 的t BuOMe 中进行的。未反应的 β-氨基酯对映体 (1 R ,2 S ) 和产物 β-氨基酸对映体 (1 S , 2 R ) 的对映体过量 ( ee ) 值适中至极佳( ee s > 62% 和ee p> 96%) 和良好的化学收率 (>25%) 在一个或两个步骤中。对映异构体很容易通过有机溶剂/H 2 O 萃取分离。
• Nylon-3 polymers active against Clostridium difficile
  申请人：Wisconsin Alumni Research Foundation

  公开号：US10463688B2

  公开（公告）日：2019-11-05

  A method and corresponding composition to inhibit outgrowth of C. difficile spores and/or to inhibit growth of C. difficile vegetative cells in a mammal in which an amount of a nylon-3 polymer or nylon-3 copolymer or a pharmaceutically suitable salt thereof is administered to the subject.

  一种抑制艰难梭菌孢子生长和/或抑制艰难梭菌无性细胞在哺乳动物体内生长的方法和相应组合物，其中向受试者施用一定量的尼龙-3聚合物或尼龙-3共聚物或其药用盐。