9-azabicyclo<6.2.0>decan-10-one | 4946-36-5

• 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: 9-azabicyclo<6.2.0>decan-10-one
• 英文别名: 9-aza-bicyclo[6.2.0]decan-10-one；9-Azabicyclo[6.2.0]decan-10-one
• CAS: 4946-36-5
• 化学式: C₉H₁₅NO
• mdl: MFCD21758424
• 分子量: 153.224
• InChiKey: IRZLUTQKGLCRPL-UHFFFAOYSA-N

物化性质

• 沸点：
  321.4±11.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.888
• 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：

  甲醇 、 9-azabicyclo<6.2.0>decan-10-one 在 SiO₂-Cl 、 碳酸氢钠 作用下， 反应 0.33h， 以82%的产率得到Methyl 2-aminocyclooctane-1-carboxylate
  参考文献：
  名称：

  Highly Efficient Methanolysis of Bicyclic β-Lactams to β-Amino Ester Using Silica Chloride

  摘要：

  氯化硅作为一种有效的异相催化剂，可用于在弱酸性条件下对高度受限的环状 β-内酰胺进行甲醇分解，以获得定量的 β-氨基酯。

  DOI：

  10.1246/cl.2006.1004
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 环辛烷 生成 9-azabicyclo<6.2.0>decan-10-one
  参考文献：
  名称：

  Electron impact and ammonia chemical ionization mass spectra ofn-azabicyclo[m.2.0]alkan-(n + 1)-ones (m = 3-6,n = 6-9)

  摘要：

  AbstractElectron impact induced fragmentation of the title compounds obeys a route where the lactam moiety, OCNH, is cleaved first, with the accompanying formation of a cycloalkene ion. This can be verified by low‐resolution, high‐resolution, B/E and B2/E spectra as well as by collisional activation spectra of, for example, the ions m/z 82 and 67 from 7‐azabicyclo[4.2.0]octan‐8‐one and from cyclohexene. The only, and fairly weak, fragment ions including O and N are [C3H3O]+, [CkH2k‐2N]+ (k = 5–8) and [C3H6N]+. The ammonia chemical ionization spectra are also characteristic for all four lactams and show the same dominant ions in all cases, namely [M + 1]+, [M + 1 + NH3]+˙ and [2 M + 1]+˙.

  DOI：

  10.1002/oms.1210210202

文献信息

• Poly-β-peptides from functionalized β-lactam monomers and antibacterial compositions containing same
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US10323121B2

  公开（公告）日：2019-06-18

  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.

  本发明公开了一种制造β-多肽的方法。该方法包括在碱引发剂和非含金属分子的助引发剂存在下，使含β-内酰胺的单体聚合，生成β-多肽。具体公开的方法是碱引发剂为叔丁醇钾、双（三甲基硅基）酰胺锂（LiN(TMS)2）、双（三甲基硅基）酰胺钾和乙醇钠，反应在氯仿、二氯甲烷、二甲亚砜或四氢呋喃等溶剂中进行。
• Nylon-3 co-polymers and synthetic lung surfactant compositions containing same
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US10736915B2

  公开（公告）日：2020-08-11

  Non-natural oligomers have recently shown promise as functional analogues of lung surfactant proteins B and C (SP-B and SP-C), two helical and amphiphilic proteins that are critical for normal respiration. The generation of non-natural mimics of SP-B and SP-C has previously been restricted 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-B mimicry that is based on sequence-random copolymers containing cationic and lipophilic subunits. These materials, members of the nylon-3 family, are prepared by ring-opening polymerization of β-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. Attachment of an N-terminal octadecanoyl unit to the nylon-3 copolymers affords further improvements by reducing the percent surface area compression to reach low minimum surface tension.

  非天然低聚物最近有望成为肺表面活性蛋白 B 和 C（SP-B 和 SP-C）的功能类似物，这两种螺旋状两亲性蛋白对正常呼吸至关重要。以前，SP-B 和 SP-C 的非天然模拟物的生成一直局限于分步、序列特异性合成，从而产生离散的低聚物，以显示特定的结构属性。本文介绍的另一种 SP-B 拟态方法是基于含有阳离子和亲油亚单位的序列随机共聚物。这些材料属于尼龙-3 家族，是通过 β-内酰胺的开环聚合反应制备的。最好的尼龙-3 聚合物在混合脂膜中显示出良好的体外表面活性。脉动气泡表面活性测定法的数据表明，含有表面活性最强的聚合物的薄膜所具有的吸附性和动态循环特性超过了用于模拟 SP-B 的离散肽。在尼龙-3 共聚物上连接一个 N 端十八碳酰单位可降低表面积压缩百分比，从而达到较低的最小表面张力，从而进一步提高了性能。
• Fused-ring metallamacrocyclic mercury/lanthanide complexes formed by fused-ring lactams
  作者：David M.L. Goodgame、Stuart P.W. Hill、Roger Lincoln、Miguel Quiros、David J. Williams

  DOI：10.1016/s0277-5387(00)80055-8

  日期：1993.12

  Mercury(II) acetate reacts with the fused-ring lactams (I) and lanthanide(III) nitrates, Ln = La Gd (Pm not studied), to give [LnHg2L4(NO3)3]n and with Y and Ln = Tb-Yb to yield [Y2Hg3L6(NO3)6]n and [Ln2Hg3L6(NO3)6]n. respectively. Each set of compounds forms an isostructural series. For the ligand Ic representative members of each series (Ln = Nd and Er, respectively) have been characterized by single-crystal X-ray diffraction methods. Both compounds form two-dimensional polymeric metallamacrocyclic arrays. They differ in the sense that the erbiuM complex comprises sheets of contiguous 48-membered rings, whereas in the neodymium compound two sizes of metallamacrocyclic coexist-one 48-membered and one 16-membered, which are fused together. The erbium ion is nine-coordinate and the neodymium atom 10-coordinate. The nitrate anions are involved in weak intra- and intermolecular interactions within the macrocycles.
• POLY-BETA-PEPTIDES FROM FUNCTIONALIZED BETA-LACTAM MONOMERS AND ANTIBACTERIAL COMPOSITIONS CONTAINING SAME
  申请人：Stahl Shannon S.

  公开号：US20100222250A1

  公开（公告）日：2010-09-02

  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：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：US20180153928A1

  公开（公告）日：2018-06-07

  Non-natural oligomers have recently shown promise as functional analogues of lung surfactant proteins B and C (SP-B and SP-C), two helical and amphiphilic proteins that are critical for normal respiration. The generation of non-natural mimics of SP-B and SP-C has previously been restricted 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-B mimicry that is based on sequence-random copolymers containing cationic and lipophilic subunits. These materials, members of the nylon-3 family, are prepared by ring-opening polymerization of β-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. Attachment of an N-terminal octadecanoyl unit to the nylon-3 copolymers affords further improvements by reducing the percent surface area compression to reach low minimum surface tension.