(1S,2S,3S,4S,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo<4.3.0.0<2,4>>nonane-3-carboxamide | 220623-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1S,2S,3S,4S,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo<4.3.0.0<2,4>>nonane-3-carboxamide
• 英文别名: (3R,5aS,6S,6aS,6bS)-5-oxo-3-phenylhexahydro-3H-cyclopropa[3,4]pyrrolo[1,2-c]oxazole-6-carboxamide；(1S,2S,3S,4S,7R)-5-oxo-7-phenyl-8-oxa-6-azatricyclo[4.3.0.02,4]nonane-3-carboxamide
• CAS: 220623-16-5
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: GLPZVURCOIWCIG-ADADXYTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,4S,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo<4.3.0.0<2,4>>nonane-3-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (1S,2S,5S,6R)-6-(aminomethyl)-3-aza-3-benzylbicyclo<3.1.0>hexyl-2-methanol
  参考文献：
  名称：

  WO2020150372A5

  摘要：

  公开号：

  WO2020150372A5
• 作为产物：
  描述：

  (3R,7aS)-3-phenyl-3,7a-dihydro-1H-pyrrolo[1,2-c]oxazol-5-one 在 methylsulfinylcarbanion 、 氨 、 水 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 71.0h， 生成 (1S,2S,3S,4S,7R)-6-aza-8-oxa-5-oxo-7-phenyltricyclo<4.3.0.0<2,4>>nonane-3-carboxamide
  参考文献：
  名称：

  Cyclopropanation Reactions of Pyroglutamic Acid-Derived Synthons with Akylidene Transfer Reagents

  摘要：

  The cyclopropanation of unsaturated lactams 1 and 3 derived from pyroglutamic acid with nucleophilic alkylidene transfer reagents is investigated. Good-to-modest yields of cyclopropanes were obtained with most sulfur ylides explored. Syn/anti selectivity was found to be dependent on the synthon as well as the sulfur ylide. This cyclopropanation methodology is used in the synthesis of arginine and glutamic acid analogues.

  DOI：

  10.1021/jo9816109

文献信息

• WO2020150372A5
  申请人：——

  公开号：WO2020150372A5

  公开（公告）日：2023-01-26
• Solid-Phase Guanidinylation as a Diversification Strategy of Poly-<scp>l</scp>-proline Type II Peptide Mimic Scaffolds
  作者：Ahmed Mamai、Jose S. Madalengoitia

  DOI：10.1021/ol0069711

  日期：2001.2.1

  [GRAPHICS]Solid phase guanidinylation of praline templated amino acids is studied as a diversification strategy of poly-L-proline type tl scaffolds.
• ANTIMICROBIAL COMPOUNDS AND METHODS
  申请人：Curza Global LLC

  公开号：EP3911643A1

  公开（公告）日：2021-11-24
• [EN] ANTIMICROBIAL COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS ANTIMICROBIENS ET PROCÉDÉS
  申请人：CURZA GLOBAL LLC

  公开号：WO2020150372A1

  公开（公告）日：2020-07-23

  The invention is directed to compounds that are active as antibacterial agents. The invention compounds are active against gram-positive and gram-negative bacteria and can be used to treat infections caused by gram-positive and gram-negative bacteria. Also disclosed are processes and intermediates for making the compounds.
• Strategies for the Solid-Phase Diversification of Poly-<scp>l</scp>-proline-Type II Peptide Mimic Scaffolds and Peptide Scaffolds Through Guanidinylation
  作者：Stevenson Flemer、Alexander Wurthmann、Ahmed Mamai、José S. Madalengoitia

  DOI：10.1021/jo8012258

  日期：2008.10.3

  A strategy for the solid-phase diversification of PPII mimic scaffolds through guanidinylation is presented. The approach involves the synthesis N-Pinc-N'-alkyl thioureas as diversification reagents. Analogues of Fmoc-Orn(Mtt)-OH can be incorporated into a growing peptide chain on Wang resin. Side chain deprotection with 1% TFA/CH(2)Cl(2) followed by EDCI-mediated reaction of N-Pmc-N'-alkyl thioureas with the side chain amine affords arginine analogues with modified guanidine head groups. The scope, limitations, and incidental chemistry are discussed.