2-(naphthalen-2-ylmethoxy)acetic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(naphthalen-2-ylmethoxy)acetic acid
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: CHEIPWDKCHTIEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(naphthalen-2-ylmethoxy)acetic acid 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成
  参考文献：
  名称：

  相转移催化的不对称酰基咪唑烷基化。

  摘要：

  在2-辛基吡啶鎓催化剂的相转移条件下，将2-酰基咪唑与烯丙基和苄基亲电子试剂在-40℃下以高收率和优异的对映选择性（79至> 99％ee）烷基化。酰基咪唑底物由溴乙酸经N-酰基吗啉加合物分三步制备。该催化剂以高纯度制备，可在温和条件下形成S产物（6-20小时），这与离子对机理相符。使用三氟甲磺酸甲酯和甲醇钠，经由二甲基酰基咪唑鎓中间体容易地将产物转化为有用的酯产物，而没有外消旋作用。该过程是有效的，直接的，并且适合于通过烯醇化中间体进行的其他亲电试剂和转化。

  DOI：

  10.1021/ol702197r
• 作为产物：
  描述：

  2-(naphthalen-2-ylmethoxy)propane-1,3-diol 在 氧气 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以59%的产率得到2-萘甲酸
  参考文献：
  名称：

  甘油转化为高价值化学品：利用自然资源合成非天然α-氨基酸的含义

  摘要：

  甘油衍生物是一类重要的化合物，作为有机合成中的基本结构基石具有很大的应用前景。使用NaO t Bu-O 2系统将O-苄基甘油氧化以高收率生产高价值的化合物。此外，通过将其转化为非天然的α-氨基酸证明了所得产物的合成效用，从而表明了甘油生物质的增值。

  DOI：

  10.1039/c9gc00755e

文献信息

• Phase-Transfer-Catalyzed Asymmetric Acylimidazole Alkylation
  作者：Merritt B. Andrus、Michael A. Christiansen、Erik J. Hicken、Morgan J. Gainer、D. Karl Bedke、Kaid C. Harper、Shawn R. Mikkelson、Daniel S. Dodson、David T. Harris

  DOI：10.1021/ol702197r

  日期：2007.11.1

  2-Acylimidazoles are alkylated under phase-transfer conditions with cinchonidinium catalysts at -40 degrees C with allyl and benzyl electrophiles in high yield with excellent enantioselectivity (79 to >99% ee). The acylimidazole substrates are made in three steps from bromoacetic acid via the N-acylmorpholine adduct. The catalyst is made in high purity allowing for S-product formation (6-20 h) under

  在2-辛基吡啶鎓催化剂的相转移条件下，将2-酰基咪唑与烯丙基和苄基亲电子试剂在-40℃下以高收率和优异的对映选择性（79至> 99％ee）烷基化。酰基咪唑底物由溴乙酸经N-酰基吗啉加合物分三步制备。该催化剂以高纯度制备，可在温和条件下形成S产物（6-20小时），这与离子对机理相符。使用三氟甲磺酸甲酯和甲醇钠，经由二甲基酰基咪唑鎓中间体容易地将产物转化为有用的酯产物，而没有外消旋作用。该过程是有效的，直接的，并且适合于通过烯醇化中间体进行的其他亲电试剂和转化。
• Cyclic tetrapeptide compound and use thereof
  申请人：Satoh Shigeki

  公开号：US20060229236A1

  公开（公告）日：2006-10-12

  A cyclic tetrapeptide compound of the formula (I): wherein R 1 is hydrogen; R 2 is lower alkyl, aryl, optionally substituted ar(lower)alkyl, heterocyclic(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, lower alkylcarbamoyl(lower)alkyl or arylcarbamoyl(lower)alkyl; R 3 and R 4 are each independently hydrogen, lower alkyl, optionally substituted ar(lower)alkyl, optionally substituted heterocyclic(lower)alkyl or cyclo(lower)alkyl(lower)alkyl, or R 3 and R 4 are linked together to form lower alkylene or condensed ring, or one of R 3 and R 4 is linked to the adjacent nitrogen atom to form a ring; R 5 is lower alkylene or lower alkenylene, Y is [wherein R Y1 is hydrogen, halogen or optionally protected hydroxy, R Y2 is hydrogen, halogen, lower alkyl or phenyl, and R Y3 is hydrogen or lower alkyl]; R 8 is hydrogen or lower alkyl; and n is an integer of 1 or 2, or a salt thereof.

  公式（I）的环状四肽化合物：其中R1为氢；R2为低碳基、芳基、可选取代的芳基（较低）烷基、杂环（较低）烷基、环（较低）烷基（较低）烷基、低碳基氨基（较低）烷基或芳基氨基（较低）烷基；R3和R4各自独立地为氢、低碳基、可选取代的芳基（较低）烷基、可选取代的杂环（较低）烷基或环（较低）烷基（较低）烷基，或者R3和R4结合形成低碳基亚烷基或缩合环，或者R3和R4中的一个与相邻的氮原子结合形成环；R5为低碳基亚烷基或低碳基烯烃基，Y为[其中RY1为氢、卤素或可选保护的羟基，RY2为氢、卤素、低碳基或苯基，RY3为氢或低碳基]；R8为氢或低碳基；n为1或2的整数，或其盐。
• CYCLIC TETRAPEPTIDE COMPOUND AND USE THEREOF
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP1458746A2

  公开（公告）日：2004-09-22
• [EN] CYCLIC TETRAPEPTIDE COMPOUND AND USE THEREOF<br/>[FR] COMPOSE TETRAPEPTIDE CYCLIQUE ET UTILISATION ASSOCIEE
  申请人：FUJISAWA PHARMACEUTICAL CO

  公开号：WO2003057722A2

  公开（公告）日：2003-07-17

  A cyclic tetrapeptide compound of the formula (I): wherein R1 is hydrogen; R2 is lower alkyl, aryl, optionally substituted ar(lower)alkyl, heterocyclic(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, lower alkylcarbamoyl(lower)alkyl or arylcarbamoyl(lower)alkyl; R3 and R4 are each independently hydrogen, lower alkyl, optionally substituted ar(lower)alkyl, optionally substituted heterocyclic(lower)alkyl or cyclo(lower)alkyl(lower)alkyl, or R3 and R4 are linked together to form lower alkylene or condensed ring, or one of R3 and R4 is linked to the adjacent nitrogen atom to form a ring; R5 is lower alkylene or lower alkenylene, Y is [wherein RY1 is hydrogen, halogen or optionally protected hydroxy, RY2 is hydrogen, halogen, lower alkyl or phenyl, and RY3 is hydrogen or lower alkyl]; R8 is hydrogen or lower alkyl; and n is an integer of 1 or 2, or a salt thereof.
• Discovery of 1,4-Benzodiazepine-2,5-dione (BZD) Derivatives as Dual Nucleotide Binding Oligomerization Domain Containing 1/2 (NOD1/NOD2) Antagonists Sensitizing Paclitaxel (PTX) To Suppress Lewis Lung Carcinoma (LLC) Growth in Vivo
  作者：Suhua Wang、Jingshu Yang、Xueyuan Li、Zijie Liu、Youzhen Wu、Guangxu Si、Yiran Tao、Nan Zhao、Xiao Hu、Yao Ma、Gang Liu

  DOI：10.1021/acs.jmedchem.7b00608

  日期：2017.6.22

  Nucleotide-binding oligomerization domain-like receptors (NLRs) are intracellular sensors of pathogen-associated molecular patterns (PAMPs) and damage-associated molecular patterns (DAMPs). Previously, we reported nucleotide-binding oligomerization domain-containing protein 1 (NOD1) antagonists (II, 12) and a NOD2 antagonist (9) that sensitized docetaxel (DTX) or paclitaxel (PTX) treatment for breast or lung cancer. In this article, we describe for the first time a 1,4-benzodiazepine-2,5-dione (BZD) derivative (26bh) that acts as a dual NOD1/NOD2 antagonist and inhibits both nuclear factor kappa B (NF-kappa B) and mitogen-activated protein kinase (MAPK) inflammatory signaling, thereby sensitizing PTX to suppress Lewis lung carcinoma (LLC) growth. After investigation of the compound's cytotoxicity, a systematic structure-activity relationship (SAR) was completed and revealed several key factors that were necessary to maintain antagonistic ability. This study establishes the possibility for using adjuvant treatment to combat cancer by antagonizing both NOD1 and NOD2 signaling.