2-萘羧酸,3-(苯基甲氧基)- | 128019-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-萘羧酸,3-(苯基甲氧基)-
• 英文名称: 3-benzyloxy-[2]naphthoic acid
• 英文别名: 3-Benzyloxy-[2]naphthoesaeure；2-Naphthalenecarboxylic acid, 3-(phenylmethoxy)-；3-phenylmethoxynaphthalene-2-carboxylic acid
• CAS: 128019-31-8
• 化学式: C₁₈H₁₄O₃
• mdl: MFCD00526545
• 分子量: 278.307
• InChiKey: BPWLGUHJSQRCJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.055
• 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-萘羧酸,3-(苯基甲氧基)- 在 palladium on activated charcoal 三乙基硅烷 、 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 正丁基锂 、 cerium(III) chloride 、 sodium iodate 、 (PhSeO)2O 、 四丁基氟化铵 、 氢气 、 potassium carbonate 、 三氟乙酸 、 potassium iodide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 丙酮 、 叔丁醇 为溶剂， 反应 7.0h， 生成 C52WZ2Q5T4
  参考文献：
  名称：

  1,2-萘醌衍生物的合成和PTP1B抑制作为有效的抗糖尿病药。

  摘要：

  通过各种合成方法合成了一系列新的1,2-萘醌衍生物，并对其抑制蛋白酪氨酸磷酸酶1B（PTP1B）的能力进行了评估。在R（4）位置具有取代基的1,2-萘醌衍生物显示出亚微摩尔抑制活性，化合物24对所测试的磷酸酶表现出10至60倍的选择性。此外，几种在R（3），R（6），R（7）或/和R（8）处具有取代基的4-芳基-1,2-萘醌衍生物显示出亚微摩尔抑制活性和良好的血浆稳定性。

  DOI：

  10.1016/s0960-894x(02)00331-1
• 作为产物：
  描述：

  3-benzyloxy-naphthalene-2-carboxylic acid, benzyl ester 在 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 6.0h， 生成 2-萘羧酸,3-(苯基甲氧基)-
  参考文献：
  名称：

  铜催化好氧氧化交叉偶联对映体合成3,3'-双取代的2-氨基-2'-羟基-1,1'-联萘

  摘要：

  首次成功开发了具有挑战性的2-萘胺和2-萘酚的直接不对称催化好氧氧化交叉偶联，使用新型Cu I / SPDO系统。获得了对映体富集的3,3'-双取代NOBIN，可以很容易地衍生出不同的手性配体和催化剂。该反应具有高对映选择性（高达96％ee）和良好的产率（高达80％）。在DFT计算表明，CF之间在F-H相互作用3的L17和2-萘酚的H-1,8，和两个联接伙伴之间的π-π堆叠可以在这个交叉偶联反应的enantiocontrol起到至关重要的作用。

  DOI：

  10.1002/anie.202015001

文献信息

• Preparation of enantioenriched helical- and axial-chiral molecules by dynamic asymmetric induction
  作者：Yuuya Kawasaki、Ryota Kamikubo、Yuta Kumegawa、Kouhei Ogawa、Takeru Kashiwagi、Yusuke Ano、Kazunobu Igawa、Katsuhiko Tomooka

  DOI：10.1039/d1cc05881a

  日期：——

  Dynamic asymmetric induction (DYASIN) of racemic dynamic chiral heterohelicenes afforded their highly enantioenriched forms (up to 96% ep) in quantitative yields. These heterohelicenes were readily converted into semi-static axial-chiral 1,1′-binaphthyl derivatives in a stereospecific manner.

  外消旋动态手性异螺旋烯的动态不对称诱导 (DYASIN) 以定量产率提供了它们高度对映体富集的形式（高达 96% ep）。这些异螺旋烯很容易以立体定向的方式转化为半静态轴向手性 1,1'-联萘衍生物。
• INHIBITORS OF VIRAL REPLICATION, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES
  申请人：Chasset Sophie

  公开号：US20140031338A1

  公开（公告）日：2014-01-30

  The present invention relates to compounds, their use in the treatment or the prevention of viral disorders, including HIV.

  本发明涉及化合物及其在治疗或预防病毒性疾病，包括HIV方面的应用。
• Cohen; Dudley, Journal of the Chemical Society, 1910, vol. 97, p. 1747
  作者：Cohen、Dudley

  DOI：——

  日期：——
• Synthesis of key sandramycin analogs: systematic examination of the intercalation chromophore
  作者：Dale L. Boger、Jyun-Hung Chen、Kurt W. Saionz、Qing Jin

  DOI：10.1016/s0968-0896(97)10014-1

  日期：1998.1

  The preparation and examination of 2-22 constituting a systematic study of the chromophore of sandramycin (1) are detailed. Fluorescence quenching studies were used to establish binding constants for 1-24 within calf thymus DNA, within a single high affinity bis-intercalation binding site 5'-d(GCATGC)(2), and to establish the preference for sandramycin binding to 5'-d(GCXXGC)(2) where XX = AT, TA, GC, and CG. From the latter studies, sandramycin was found to exhibit a preference that follows the order: 5'-d(GCATGC)(2) > 5'-d(GCGCGC)(2), Delta Delta G degrees = 0.3 kcal/mol > 5'-d(GCTAGC)(2), 5'-d(GCCGGC)(2), Delta Delta G degrees = 0.6 kcal/mol although it binds with high affinity to all four deoxyoligonucleotides. The two highest affinity sequences constitute repeating 5'-PuPy motifs with each intercalation event occurring at a 5'-PyPu step. The most effective sequence constitutes the less stable duplex, contains the sterically most accessible minor groove central to the bis-intercalation site, and the ability to accept two gly-NH/T C2 carbonyl H-bonds identified in prior NMR studies. Similarly, the contribution of the individual structural features of the chromophore were assessed with the high affinity duplex sequence 5'-d(GCATGC)(2). To a first approximation, the cytotoxic properties were found to parallel trends established in the DNA binding affinities. The exception to this generalization was 4 which lacks the sandramycin chromophore phenol. Although typically 4-10x less potent than sandramycin against leukemia cell lines, it proved to be 1-10,000x more potent against melanomas, carcinomas, and adenocarcinomas exhibiting IC50 values of IpM-10 nM placing it among the most potent agents identified to date. Additionally, the first disclosure of the HIV-1 reverse transcriptase inhibitory activity of sandramycin (1) as well as that of its key analogs are described and define the chromophore structural features required for their exceptional potency. Two analogs, 18 and 3, roughly maintain the HIV-I reverse transcriptase inhibitory potency of 1 but exhibit substantially diminished cytotoxic activity (10(2) - 10(3)x). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Amino acid derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0346847B1

  公开（公告）日：1994-05-11