7-azabicyclo[4.2.0]oct-3-en-8-one

• 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]oct-3-en-8-one
• 英文别名: (1S,6R)-7-azabicyclo[4.2.0]oct-3-en-8-one
• 化学式: C₇H₉NO
• 分子量: 123.155
• InChiKey: IHROAFZNBVGGFN-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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]oct-3-en-8-one 在 盐酸 、 水 作用下， 生成 cis-6-Amino-3-cyclohexene-1-carboxylic acid hydrochloride
  参考文献：
  名称：

  具有 Conduritol F 结构的新型 2,3-Diaminoconduritol 的合成

  摘要：

  以环己-1,4-二烯为原料制备了一种新的具有 conduritol F 结构的 2,3-diaminoconduritol 衍生物。最初，通过氯磺酰基异氰酸酯 (CSI) 与环己-1,4-二烯的环加成反应制备的内酰胺转化为氨基酸。酸官能团转化为异氰酸酯导致形成咪唑烷酮衍生物，通过分子内环化形成。在这项工作的第二部分，已知的酸酐，3a,4,7,7a-四氢异苯并呋喃-1,3-二酮被成功转化为所需的双（氨基甲酸酯）。六元环中双键的溴化，然后是 DBU 诱导的（DBU = 1,8-二氮杂双环 [5.4.0] undec-7-ene）HBr 消除提供了对称的二烯。二烯单元的光氧化提供双环内过氧化物。内过氧化物与硫脲的反应随后乙酰化导致形成顺式构型的二乙酸酯。氨基甲酸酯和乙酸酯基团的脱保护得到具有 conduritol F 结构的新 2,3-diaminoconduritol。

  DOI：

  10.1002/ejoc.201200582
• 作为产物：
  描述：

  (1S,6R)-8-oxo-7-azabicyclo[4.2.0]oct-3-ene-7-sulfonyl chloride 在 sodium sulfite 作用下， 生成 7-azabicyclo[4.2.0]oct-3-en-8-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel bicyclic β-lactams as potential antimalarials

  摘要：

  A series of bicyclic N-substituted and unsubstituted beta-lactams were synthesized and evaluated as targeted potential antimalarials. The compounds MNR4 and MNR5 were found to have highest potency against Plasmodium falciparum in vitro. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.01.011

文献信息

• Azabicyclic compounds are central nervous system active agents
  申请人：——

  公开号：US20040044029A1

  公开（公告）日：2004-03-04

  Compounds of formula (I) 1 are novel CNS active agents that are useful for treating pain and for treating other disorders associated with the cholinergic system.

  公式(I)1的化合物是新颖的中枢神经系统活性剂，用于治疗疼痛以及治疗与胆碱能系统相关的其他疾病。
• Alicyclic β- and γ-Amino Acids: Useful Scaffolds for the Stereocontrolled Access to Amino Acid-Based Carbocyclic Nucleoside Analogs
  作者：Attila Márió Remete、Loránd Kiss

  DOI：10.3390/molecules24010161

  日期：——

  Stereocontrolled synthesis of some amino acid-based carbocyclic nucleoside analogs containing ring C=C bond has been performed on β- and γ-lactam basis. Key steps were N-arylation of readily available β- or γ-lactam-derived amino ester isomers and amino alcohols with 5-amino-4,6-dichloropyrimidine; ring closure of the formed adduct with HC(OMe)₃ and nucleophilic displacement of chlorine with various

  已经在β-和γ-内酰胺的基础上进行了一些含环C = C键的氨基酸基碳环核苷类似物的立体控制合成。关键步骤是将容易获得的β-或γ-内酰胺衍生的氨基酯异构体和氨基醇与5-氨基-4,6-二氯嘧啶进行N-芳基化；用HC（OMe）3闭环形成的加合物，并在所得6-氯嘌呤部分中用各种N-亲核试剂亲和置换氯。
• Synthesis of carbapenems with a sulfonyl group in the C-6 side-chain and their biological activity.
  作者：NORIKAZU TAMURA、HIDEAKI NATSUGARI、YASUHIKO KAWANO、YOSHIHIRO MATSUSHITA、KOUICHI YOSHIOKA、MICHIHIKO OCHIAI

  DOI：10.1248/cpb.35.996

  日期：——

  A new type of 5, 6-cis-carbapenems (racemic) having a sulfonyl group in the C-6 side-chain were synthesized by employing the synthetic methodology reported in our previous papers, and an alternative stereocontrolled synthesis of these 5, 6-cis-carbapenems was achieved starting from 8-oxo-7-azabicyclo [4.2.0] oct-3-ene (14) via an intramolecular aldol condensation as the key step. Chiral 5, 6-cis-carbapenems were also synthesized from (1S, 6R) -8-oxo-7-azabicyclo [4.2.0] oct-3-ene (29), which was derived from cis-1, 2, 5, 6-tetrahydrophthalic anhydride. The carbapenems thus obtained proved to be highly stable to the mouse kidney homogenate, and most of them showed good antibacterial activity as well as potent β-lactamase inhibitory activity.

  利用我们之前论文中报道的合成方法，合成了一种新型5,6-顺式-碳青霉烯类化合物（外消旋体），其C-6侧链上含有磺酰基团。通过以分子内aldol缩合作为关键步骤，从8-氧代-7-氮杂双环[4.2.0]辛-3-烯（14）开始，实现了这些5,6-顺式-碳青霉烯类化合物的替代立体控制合成。从顺-1,2,5,6-四氢邻苯二甲酸酐衍生得到的(1S,6R)-8-氧代-7-氮杂双环[4.2.0]辛-3-烯（29），也合成了手性5,6-顺式-碳青霉烯类化合物。所得到的碳青霉烯类化合物在鼠肾匀浆中表现出高稳定性，其中大多数化合物不仅具有良好的抗菌活性，还显示出强效的β-内酰胺酶抑制活性。
• Synthesis of fluorinated piperidine and azepane β-amino acid derivatives
  作者：Renáta Anita Ábrahámi、Loránd Kiss、Pablo Barrio、Ferenc Fülöp

  DOI：10.1016/j.tet.2016.10.005

  日期：2016.11

  A convenient and robust stereocontrolled procedure has been developed for the synthesis of novel trifluoromethyl-containing piperidine and azepane β-amino ester stereoisomers. The synthesis started from readily available unsaturated bicyclic β-lactams and was based on oxidative cleavage of the ring CC double bond followed by ring closure of the diformyl intermediates in the presence of 2,2,2-trifluoroethylamine

  已经开发了方便且鲁棒的立体控制方法，用于合成新型的含三氟甲基的哌啶和氮杂环庚烷β-氨基酯立体异构体。合成从容易获得的不饱和双环β-内酰胺开始，并且基于环CC双键的氧化裂解，然后在2,2,2-三氟乙胺盐酸盐存在下通过还原胺化对二甲酰基中间体进行闭环。合成方法已有效地扩展到单氟化和二氟化类似物的合成。
• cis-2-Aminocyclohex-4-enecarboxylic acid as a new building block of helical foldamers
  作者：Sunmi Kwon、Philjae Kang、Moon-Gun Choi、Soo Hyuk Choi

  DOI：10.1039/c4nj02056a

  日期：——

  cis-2-Aminocyclohex-4-enecarboxylic acid (cis-ACHE) is a conformationally constrained β-amino acid. We showed that the conformational preference of a cis-ACHE residue is similar to that of cis-2-aminocyclohexanecarboxylic acid. α/β-Peptides that consist of the alternation of (1S,2R)-cis-ACHE and L-alanine adopted 11/9-helical conformations in solution and in the crystal state.

  顺式-2-氨基环己基-4-烯羧酸（顺式-ACHE）是一种构象受限的β-氨基酸。我们表明，顺式-ACHE残基的构象偏好类似于顺式-2-氨基环己烷羧酸。由（1 S，2 R）-顺式-ACHE和L-丙氨酸交替组成的α/β-肽在溶液和晶体状态下均采用11/9螺旋构象。