(1S,12R)-13-Aza-bicyclo[10.2.0]tetradecan-14-one | 929296-20-8

• 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: (1S,12R)-13-Aza-bicyclo[10.2.0]tetradecan-14-one
• 英文别名: (1S,12R)-13-azabicyclo[10.2.0]tetradecan-14-one
• CAS: 929296-20-8
• 化学式: C₁₃H₂₃NO
• 分子量: 209.332
• InChiKey: QZGCOFZRRZPWHB-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (1S,12R)-13-Aza-bicyclo[10.2.0]tetradecan-14-one 在 盐酸 作用下， 以 水 为溶剂， 反应 3.0h， 以89%的产率得到(1S,2R)-2-Amino-cyclododecanecarboxylic acid; hydrochloride
  参考文献：
  名称：

  Do lipases also catalyse the ring cleavage of inactivated cyclic trans-β-lactams?

  摘要：

  Twelve-membered cyclic cis- and trans-beta-lactams 1b and 2b and the corresponding cyclic cis- and trans-beta-amino acid enantiomers, 1a, 1e and 2a, 2c were prepared through the CAL-B-catalysed enantio selective ring cleavage of racemic cis-13-azabicyclo[10.2.0]tetradecan-14-one, (+/-)-1, and trans-13-azabicyclo[10.2.0]tetradecan-14-one, (+/-)-2. High enantioselectivities (E > 200) were observed for the ring opening of both the cis- and trans-beta-lactams when the Lipolase-catalysed reactions were performed with 0.5 equiv of H2O in i-Pr2O at 70 degrees C. The resolved beta-lactams 1b and 2b (yield >= 47%) and beta-amino acids 1a and 2a (yield >= 32%) could be easily separated. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.030
• 作为产物：
  描述：

  (+/-)-cis-13-azabicyclo[10.2.0]tetradecan-14-one 在 Lipolase C_. antarctica lipase B 作用下， 以 异丙醚 、 水 为溶剂， 反应 18.0h， 以39%的产率得到(1R,2S)-2-Amino-cyclododecanecarboxylic acid
  参考文献：
  名称：

  Do lipases also catalyse the ring cleavage of inactivated cyclic trans-β-lactams?

  摘要：

  Twelve-membered cyclic cis- and trans-beta-lactams 1b and 2b and the corresponding cyclic cis- and trans-beta-amino acid enantiomers, 1a, 1e and 2a, 2c were prepared through the CAL-B-catalysed enantio selective ring cleavage of racemic cis-13-azabicyclo[10.2.0]tetradecan-14-one, (+/-)-1, and trans-13-azabicyclo[10.2.0]tetradecan-14-one, (+/-)-2. High enantioselectivities (E > 200) were observed for the ring opening of both the cis- and trans-beta-lactams when the Lipolase-catalysed reactions were performed with 0.5 equiv of H2O in i-Pr2O at 70 degrees C. The resolved beta-lactams 1b and 2b (yield >= 47%) and beta-amino acids 1a and 2a (yield >= 32%) could be easily separated. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2006.11.030

文献信息

• 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.
• POLY-BETA-PEPTIDES FROM FUNCTIONALIZED BETA-LACTAM MONOMERS AND ANTIBACTERIAL COMPOSITIONS CONTAINING SAME
  申请人：Stahl Shannon S.

  公开号：US20110196127A1

  公开（公告）日：2011-08-11

  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.
• US7951912B2
  申请人：——

  公开号：US7951912B2

  公开（公告）日：2011-05-31
• US8519095B2
  申请人：——

  公开号：US8519095B2

  公开（公告）日：2013-08-27