2-norbornylacetic acid | 6485-19-4

• 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: 2-norbornylacetic acid
• 英文别名: bicyclo[2.2.1]heptan-2-ylacetic acid；exo-Norbornylessigsaeure；exo-Norbornyl-(2)-essigsaeure；(+/-)-(2exo-Norbornyl)-essigsaeure；(+/-)-2-(exo-bicyclo[2.2.1]heptan-2-yl)acetic acid；(+/-)-(exo)-2-norbornaneacetic acid；rac-2-[(1R,2S,4S)-bicyclo[2.2.1]heptan-2-yl]aceticacid；2-[(1R,2S,4S)-2-bicyclo[2.2.1]heptanyl]acetic acid
• CAS: 6485-19-4
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: FYHBMPWRHCWNBC-RNJXMRFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-norbornylacetic acid 在 盐酸 、 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.17h， 生成 8-(1R,2S,4S)-1-Bicyclo[2.2.1]hept-2-ylmethyl-1,3-dipropyl-3,7-dihydro-purine-2,6-dione
  参考文献：
  名称：

  8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors

  摘要：

  With the aim of characterizing the hydrophobic interactions between xanthines and the A1 receptor site, 1,3-dipropyl-8-substituted xanthines were synthesized. Introduction of a quaternary carbon and the conformationally restricted cyclopentyl moiety into the 8-position of xanthines enhanced the adenosine A1 antagonism. 1,3-Dipropyl-8-(3-noradamantyl)xanthine (42) was identified to be a selective and the most potent A1 receptor antagonist reported to date. Under our structure-activity relationship, the 8-substituent of xanthine antagonists and the N6-substituent of adenosine agonists appears to bind to the same region of the A1 receptor.

  DOI：

  10.1021/jm00083a018
• 作为产物：
  描述：

  exo-Norbornyl-(2)-chloressigsaeure 在 盐酸 、 汞 、 锌 作用下， 生成 2-norbornylacetic acid
  参考文献：
  名称：

  Bott,K., Chemische Berichte, 1970, vol. 103, p. 3850 - 3861

  摘要：

  DOI：

文献信息

• POTASSIUM CHANNEL MODULATORS
  申请人：Brown Brian S.

  公开号：US20110124642A1

  公开（公告）日：2011-05-26

  Disclosed herein are KCNQ potassium channels modulators of formula (I) wherein ring Z 1 , R 1 , p, R 3 , and R 4 are as defined in the specification. Compositions comprising such compounds; and methods for treating conditions and disorders using such compounds and compositions are also described.

  本文披露了具有以下结构的KCNQ钾通道调节剂（I）： 其中环Z 1 ，R 1 ，p，R 3 和R 4 如规范中所定义。还描述了包含这些化合物的组合物；以及使用这些化合物和组合物治疗疾病和疾病的方法。
• Palladium-Catalyzed Double Activation and Arylation of 2° and 3° C(sp3)–H Bonds of the Norbornane System: Formation of a C–C Bond at the Bridgehead Carbon and Bridgehead Quaternary Stereocenter
  作者：Srinivasarao Babu、Ramarao Parella

  DOI：10.1055/s-0033-1341242

  日期：——

  Pd-catalyzed activation and direct arylation of both 2° and the bridgehead 3° (sp3) C–H bonds and an unprecedented C–C bond formation at the bridgehead carbon of the norbornane system are reported. The assembly of bridgehead-substituted norbornane frameworks having contiguous stereocenters was accomplished. X-ray crystal structure analysis of representative molecules unambiguously established the stereochemistry

  据报道，Pd 催化的 2° 和桥头 3°（sp3）C-H 键的活化和直接芳基化以及在降冰片烷系统的桥头碳上形成了前所未有的 C-C 键。完成了具有连续立体中心的桥头取代降冰片烷骨架的组装。代表性分子的 X 射线晶体结构分析明确地建立了立体化学。
• Synthesis and Identification of Novel Berberine Derivatives as Potent Inhibitors against TNF-α-Induced NF-κB Activation
  作者：Yan-Xiang Wang、Lu Liu、Qing-Xuan Zeng、Tian-Yun Fan、Jian-Dong Jiang、Hong-Bin Deng、Dan-Qing Song

  DOI：10.3390/molecules22081257

  日期：——

  A preliminary mechanism study revealed that all of them could inhibit TNF-α-induced NF-κB activation via impairing IκB kinase (IKK) phosphorylation as well as cytokines interleukin (IL)-6 and IL-8 induced by TNF-α. Therefore, the results provided powerful information on further structural modifications and development of BBR derivatives into a new class of anti-inflammatory candidates for the treatment

  合成了在环D的取代基上定义的二十三种新的小碱（BBR）类似物，并评估了其抑制肿瘤坏死因子（TNF）-α诱导的核因子（NF）-κB活化的活性。结构-活性关系（SAR）分析表明，在9位上合适的叔/季碳取代基或10位上的刚性片段可能有利于增强其抗炎能力。其中，化合物2d，2e，2i和2j对NF-κB活化表现出令人满意的抑制作用，抑制率约为90％（5μM），远优于BBR。初步的机制研究表明，它们均可以通过削弱IκB激酶（IKK）磷酸化以及TNF-α诱导的细胞因子白介素（IL）-6和IL-8来抑制TNF-α诱导的NF-κB活化。所以，
• A Detailed Study of Antibacterial 3-Acyltetramic Acids and 3-Acylpiperidine-2,4-diones
  作者：Yong-Chul Jeong、Zsolt Bikadi、Eszter Hazai、Mark G. Moloney

  DOI：10.1002/cmdc.201402093

  日期：2014.5.18

  Inspired by the core fragment of antibacterial natural products such as streptolydigin, 3‐acyltetramic acids and 3‐acylpiperidine‐2,4‐diones have been synthesised from the core heterocycle by direct acylation with the substituted carboxylic acids using a strategy which permits ready access to a structurally diverse compound library. The antibacterial activity of these systems has been established against

  受到抗菌天然产物（例如链霉菌丝蛋白），3-酰基四酸和3-酰基哌啶-2,4-二酮的核心片段的启发，已通过直接与取代的羧酸进行酰化反应从核心杂环合成了一种策略，该策略允许随时使用结构上多样化的化合物库。这些系统的抗菌活性已经针对一系列革兰氏阳性和革兰氏阴性细菌而建立，并且大部分针对前者，在某些情况下非常有效。已获得与针对该文库一小部分的十一碳烯基焦磷酸合酶（UPPS）和/或RNA聚合酶（RNAP）的作用方式一致的数据。活性最高的化合物已显示出在UPPS和RNAP的链霉菌毒素和粘质激肽的已知结合位点上具有结合力。
• Addition of Carboxyalkyl Radicals to Alkenes through a Catalytic Process, Using a Mn(II)/Co(II)/O₂ Redox System
  作者：Koji Hirase、Satoshi Sakaguchi、Yasutaka Ishii

  DOI：10.1021/jo034584+

  日期：2003.7.1

  production of mono- and dicarboxylic acids by the addition of carboxyalkyl radicals to alkenes and dienes, respectively, was successfully developed through a catalytic process with use of Mn(II)/Co(II)/O(2) system. Thus, a variety of carboxylic acids were prepared by the reaction of alkenes and dienes with acid anhydrides in the presence of a very small amount of Mn(OAc)(2) (0.5 mol %) and Co(OAc)(2)

  通过使用Mn（II）/ Co（II）/ O（2）系统进行催化过程，成功开发了一种通过分别向烯烃和二烯中添加羧基烷基来生产一元羧酸和二元羧酸的新策略。因此，在非常少量的Mn（OAc）（2）（0.5 mol％）和Co（OAc）（2）（0.1摩尔％）。