methyl ((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)carbamate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl ((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)carbamate
• 英文别名: methyl (1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylcarbamate；methyl N-[(1R,2R,3R,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]carbamate
• 化学式: C₁₂H₂₁NO₂
• 分子量: 211.304
• InChiKey: FJPNFRSHCQGDQF-UTINFBMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl ((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)carbamate 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 以60%的产率得到(1R,2R,3R,5S)-N,2,6,6-tetramethylbicyclo[3.1.1]heptan-3-amine hydrochloride
  参考文献：
  名称：

  Discovery of highly potent agents against influenza A virus

  摘要：

  We previously reported several new M2 inhibitors as active as amantadine against influenza A virus and validated by three types of in vitro assays. Herein, we further modified one of the most potent hits in a viral inhibition assay and conducted structure activity relationship studies on this scaffold. As a result, compound 8e was identified to be the most potent inhibitor against wild-type influenza A virus, being nearly 240-fold more active than amantadine. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.010
• 作为产物：
  描述：

  (1R,2R,3R,5S)-(-)-Isopinocampheylamine 、 氯甲酸甲酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以89%的产率得到methyl ((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)carbamate
  参考文献：
  名称：

  [EN] PYRIDAZINONE DERIVATIVES AND USE THEREOF AS P2X7 RECEPTOR INHIBITORS
  [FR] DÉRIVÉS DE PYRIDAZINONE ET LEUR UTILISATION COMME INHIBITEURS DU RÉCEPTEUR P2X7

  摘要：

  翻译结果为：新型的哒嗪酮化合物，其化学公式为(I)，能够抑制嘌呤能P2X7受体，并对预防、治疗和改善炎症性和免疫性疾病有益。

  公开号：

  WO2009057827A1

文献信息

• [EN] PYRIDAZINONE DERIVATIVES AND USE THEREOF AS P2X7 RECEPTOR INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDAZINONE ET LEUR UTILISATION COMME INHIBITEURS DU RÉCEPTEUR P2X7
  申请人：NISSAN CHEMICAL IND LTD

  公开号：WO2009057827A1

  公开（公告）日：2009-05-07

  Novel pyridazinone compounds of formula (I), which inhibit the purinergic P2X7 receptor and are useful for prevention, therapy and improvement of inflammatory and immunological diseases.

  翻译结果为：新型的哒嗪酮化合物，其化学公式为(I)，能够抑制嘌呤能P2X7受体，并对预防、治疗和改善炎症性和免疫性疾病有益。
• PYRIDAZINONE COMPOUNDS AND P2X7 RECEPTOR INHIBITORS
  申请人：Shigeta Yukihiro

  公开号：US20100286390A1

  公开（公告）日：2010-11-11

  Novel pyridazinone compounds of formula (I), which inhibit the purinergic P2X7 receptor and are useful for prevention, therapy and improvement of inflammatory and immunological diseases.

  化合物(I)是一种新型的吡啶并嗪酮化合物，可以抑制嘌呤能P2X7受体，因此可用于预防、治疗和改善炎症和免疫性疾病。
• 1,5-Asymmetric Induction in Squarate Cascades. Conformational Control of Helicity by Chiral Amino Substituents during Conrotatory Octatetraene Cyclization Prior to β-Elimination
  作者：Leo A. Paquette、Jinsung Tae

  DOI：10.1021/jo9722921

  日期：1998.3.1

  Both the sigmatropic and electrocyclic rearrangement pathways that can arise when a pair of alkenyl anions are added to a squarate ester have high stereochemical demands. The distinction is nontrivial. When cis addition occurs initially, the stereoinduction that materializes at this point is fully transmitted into the product(s). The more commonly observed trans addition exhibits fleeting stereochemical consequences because of rapid equilibration of the octatetraenyl intermediates. In this instance, product distribution is governed by the relative rates of conrotatory cyclization at this advanced stage. Herein reported is a complete dissection of a squarate cascade when a stereogenic center attached to an amino substituent effects 1,5-asymmetric induction prior to B-elimination of the entire fragment. Deuterium labeling permits a direct measure of the contrasting kinetic imbalances associated with the two possible modes of alkenyl anion addition. Furthermore; quantitative analysis of the partitioning experienced by the two helical octatetraenes is readily accomplished. This work constitutes the first example where a complete dynamic profile for these complex processes has been possible. The fact that long-range asymmetric induction has been instrumental in solving the mechanistic puzzle is noteworthy.
• US8440666B2
  申请人：——

  公开号：US8440666B2

  公开（公告）日：2013-05-14
• Discovery of highly potent agents against influenza A virus
  作者：Xin Zhao、Chufang Li、Shaogao Zeng、Wenhui Hu

  DOI：10.1016/j.ejmech.2010.10.010

  日期：2011.1

  We previously reported several new M2 inhibitors as active as amantadine against influenza A virus and validated by three types of in vitro assays. Herein, we further modified one of the most potent hits in a viral inhibition assay and conducted structure activity relationship studies on this scaffold. As a result, compound 8e was identified to be the most potent inhibitor against wild-type influenza A virus, being nearly 240-fold more active than amantadine. (C) 2010 Elsevier Masson SAS. All rights reserved.