10-azabicyclo[6.2.0]dec-4-en-9-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: 10-azabicyclo[6.2.0]dec-4-en-9-one
• 英文别名: (1S,8R)-9-azabicyclo[6.2.0]dec-4-en-10-one；(1S,8R,4Z)-9-azabicyclo[6.2.0]dec-4-en-10-one；(1S,4Z,8R)-9-azabicyclo[6.2.0]dec-4-en-10-one
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: LGFGPHLZVAEHME-WFWQCHFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  10-azabicyclo[6.2.0]dec-4-en-9-one 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以73%的产率得到(Z)-(1S,8R)-8-Amino-cyclooct-4-enecarboxylic acid; hydrochloride
  参考文献：
  名称：

  Advanced procedure for the enzymatic ring opening of unsaturated alicyclic β-lactams

  摘要：

  Enantiopure beta-amino acids 1a-4a and beta-lactams 1b-4b were prepared simultaneously through the lipolase-catalysed enantioselective ring opening of unsaturated racemic beta-lactams (+/-)-1-(+/-)-4. High enantioselectivities (E >200) were observed when the reactions were performed with 1 equiv of water in iPr(2)O at 70degreesC. The resolved (1R,2S)-amino acids (yield greater than or equal to 45%) and (1S,5R)-, (1S,6R)- and (1S,8R)-lactams (yield greater than or equal to47%) could be easily separated. The ring opening of lactam enantiomers 1b-4b with 18% HCl afforded the corresponding beta-amino acid hydrochlorides 1c(.)HCl-4c(.)HCl (ee >95%). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.029
• 作为产物：
  描述：

  1,5-cis,cis-cyclooctadiene 在 ammonium hydroxide 、 lipase PS on Celite 、 sodium carbonate 、 potassium carbonate 、 sodium sulfate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醚 、 水 为溶剂， 反应 8.0h， 生成 10-azabicyclo[6.2.0]dec-4-en-9-one
  参考文献：
  名称：

  （1 R，8 S）-和（1 S，8 R）-9-氮杂双环[6.2.0] dec-4-en-10-one的制备：合成抗毒素-a的潜在起始化合物

  摘要：

  通过添加氯磺酰基异氰酸酯从环辛二烯获得的9-氮杂双环[6.2.0] dec-4-en-10-one（±）-2被N-羟甲基化成（±）-3，然后通过脂肪酶催化的不对称拆分（S）-成骨中心的一级羟基的酰化作用。高对映选择性（Ë当脂肪酶PS和丁酸乙烯酯在二-用于观察= 94）异-丙基醚在-15℃下，产生对映体富集酯3A和醇3B（EE≥92％）。用NH 4 OH / MeOH处理3a和3b得到相应的β-内酰胺（1 R，8 S）-2a和（1 S，8 R）-2b（ee≥93％），是抗毒素a合成中的潜在起始化合物。内酰胺的开环（±） - 2，（±） - 7，图3a和3b中，接着还原，导致外消旋4 - 6和8和对映体4A，4B，5A和5B中的八元环状β氨基酸衍生品。

  DOI：

  10.1016/s0957-4166(01)00100-8

文献信息

• Preparation of (1R,8S)- and (1S,8R)-9-azabicyclo[6.2.0]dec-4-en-10-one: potential starting compounds for the synthesis of anatoxin-a
  作者：Enikő Forró、Judit Árva、Ferenc Fülöp

  DOI：10.1016/s0957-4166(01)00100-8

  日期：2001.3

  enriched ester 3a and alcohol 3b (e.e. ≥92%). Treatment of 3a and 3b with NH4OH/MeOH afforded the corresponding β-lactams (1R,8S)-2a and (1S,8R)-2b (e.e. ≥93%), potential starting compounds in anatoxin-a synthesis. The ring opening of lactams (±)-2, (±)-7, 3a and 3b, followed by reduction, resulted in racemic 4–6 and 8 and enantiomeric 4a, 4b, 5a and 5b eight-membered cyclic β-amino acid derivatives.

  通过添加氯磺酰基异氰酸酯从环辛二烯获得的9-氮杂双环[6.2.0] dec-4-en-10-one（±）-2被N-羟甲基化成（±）-3，然后通过脂肪酶催化的不对称拆分（S）-成骨中心的一级羟基的酰化作用。高对映选择性（Ë当脂肪酶PS和丁酸乙烯酯在二-用于观察= 94）异-丙基醚在-15℃下，产生对映体富集酯3A和醇3B（EE≥92％）。用NH 4 OH / MeOH处理3a和3b得到相应的β-内酰胺（1 R，8 S）-2a和（1 S，8 R）-2b（ee≥93％），是抗毒素a合成中的潜在起始化合物。内酰胺的开环（±） - 2，（±） - 7，图3a和3b中，接着还原，导致外消旋4 - 6和8和对映体4A，4B，5A和5B中的八元环状β氨基酸衍生品。
• Helical folding of α/β-peptides containing β-amino acids with an eight-membered ring constraint
  作者：Woohyung Lee、Sunmi Kwon、Philjae Kang、Ilia A. Guzei、Soo Hyuk Choi

  DOI：10.1039/c4ob00266k

  日期：——

  αβα-Tripeptide that contains a cyclic β-amino acid with an eight-membered ring, a cis-2-aminocyclooct-5-enecarboxylic acid (cis-ACOE) or a cis-2-aminocyclooctanecarboxylic acid (cis-ACOC) displayed an 11/9-helical turn in the crystal state. The related α/β-peptide oligomers were shown to adopt 11/9-helical conformations in solution.

  包含具有八元环的环状β-氨基酸，顺式-2-氨基环辛基5-烯基羧酸（顺式-ACOE）或顺式-2-氨基环辛烷羧酸（顺式-ACOC）的αβα-三肽显示11 / 9螺旋在晶体状态下旋转。相关的α/β-肽寡聚体在溶液中显示为采用11 / 9-螺旋构象。
• Poly-beta-peptides from functionalized beta-lactam monomers and antibacterial compositions containing same
  申请人：Stahl S. Shannon

  公开号：US20070087404A1

  公开（公告）日：2007-04-19

  Disclosed is a method of making β-polypeptides. The method includes polymerizing β-lactam-containing monomers in the presence of a base initiator and a co-initiator which is not a metal-containing molecule to yield the product β-polypeptides. Specifically disclosed are methods wherein the base initiator is potassium t-butoxide, lithium bis(trimethylsilyl)amide (LiN(TMS) 2 ), potassium bis(trimethyl-silyl)amide, and sodium ethoxide, and the reaction is carried out in a solvent such as chloroform, dichloromethane, dimethylsulfoxide, or tetrahydrofuran.
• NYLON-3 CO-POLYMERS AND SYNTHETIC LUNG SURFACTANT COMPOSITIONS CONTAINING SAME
  申请人：Gellman Samuel H.

  公开号：US20130004453A1

  公开（公告）日：2013-01-03

  Non-natural oligomers have recently shown promise as functional analogues of lung surfactant proteins Band C (SP-B and SP-C), two helical and amphiphilic proteins that are clitical for normal respiration. The generation of non-natural mimics of SP-B and SP-C has previously been restlicted to step-by-step, sequence-specific synthesis, which results in discrete oligomers that are intended to manifest specific structural attributes. Presented herein an alternative approach to SP-R mimicry that is based on sequence-random copolymers containing cationic and lipophilic subunits. These materials, members of the nylon-3 family, arc prepared by ling-opening polymelization of 13-lactams. The best of the nylon-3 polymers display promising in vitro surfactant activities in a mixed lipid film. Pulsating bubble surfactometry data indicate that films containing the most surface-active polymers attain adsorptive and dynamic-cycling properties that surpass those of discrete peptides intended to mimic SP-B.
• POLY-BETA-PEPTIDES FROM FUNCTIONALIZED BETA-LACTAM MONOMERS AND ANTIBACTERIAL COMPOSITIONS CONTAINING SAME
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20150322205A1

  公开（公告）日：2015-11-12

  Disclosed is a method of making β-polypeptides. The method includes polymerizing β-lactam-containing monomers in the presence of a base initiator and a co-initiator which is not a metal-containing molecule to yield the product β-polypeptides. Specifically disclosed are methods wherein the base initiator is potassium t-butoxide, lithium bis(trimethylsilyl)amide (LiN(TMS) 2 ), potassium bis(trimethyl-silyl)amide, and sodium ethoxide, and the reaction is carried out in a solvent such as chloroform, dichloromethane, dimethylsulfoxide, or tetrahydrofuran.