(4-bromomethyl-[1]naphthyl)-methyl ether | 79997-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4-bromomethyl-[1]naphthyl)-methyl ether
• 英文别名: (4-Brommethyl-[1]naphthyl)-methyl-aether；4-Brommethyl-naphthol-(1)-methylaether；4-Methoxy-1-brommethyl-naphthalin；1-(Bromomethyl)-4-methoxynaphthalene
• CAS: 79997-03-8
• 化学式: C₁₂H₁₁BrO
• 分子量: 251.123
• InChiKey: FGNZXAGFZZCHBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-bromomethyl-[1]naphthyl)-methyl ether 在 potassium fluoride 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 以15%的产率得到1-(fluoromethyl)-4-methoxynaphthalene
  参考文献：
  名称：

  Dixon, Elisabeth A.; Fischer, Alfred; Robinson, Frank P., Canadian Journal of Chemistry, 1981, vol. 59, p. 2629 - 2641

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲氧基萘 在 吡啶 、 lithium aluminium tetrahydride 、 溴 、 碘 、 三溴化磷 、 magnesium 作用下， 以 乙醚 、 氯仿 、 苯 为溶剂， 反应 24.25h， 生成 (4-bromomethyl-[1]naphthyl)-methyl ether
  参考文献：
  名称：

  Dixon, Elisabeth A.; Fischer, Alfred; Robinson, Frank P., Canadian Journal of Chemistry, 1981, vol. 59, p. 2629 - 2641

  摘要：

  DOI：

文献信息

• Controlled Photochemical Release of Nitric Oxide from <i>O</i>²-Naphthylmethyl- and <i>O</i>²-Naphthylallyl-Substituted Diazeniumdiolates
  作者：K. Mani Bushan、Hua Xu、Patrick H. Ruane、Raechelle A. D'Sa、Christopher M. Pavlos、Joseph A. Smith、Tevye C. Celius、John P. Toscano

  DOI：10.1021/ja027957h

  日期：2002.10.1

  effect on the observed photochemistry, with the appropriate substitution pattern resulting in efficient diazeniumdiolate photorelease. Observed nitric oxide release rates from these photoprecursors are consistent with those expected for normal thermal dissociation of the diazeniumdiolate in aqueous solutions and show the same pH dependence.

  已经研究了 O2-萘基甲基-和 O2-萘基烯丙基-取代的二氮烯鎓二醇的光化学。供电子甲氧基取代对观察到的光化学具有显着影响，适当的取代模式导致有效的二氮烯二醇光释放。从这些光前体观察到的一氧化氮释放速率与二氮烯二醇在水溶液中正常热解离的预期一致，并显示出相同的 pH 依赖性。
• Visible-Light-Induced Intermolecular Dearomative Cyclization of 2-Bromo-1,3-dicarbonyl Compounds and Alkynes: Synthesis of Spiro[4.5]deca-1,6,9-trien-8-ones
  作者：Wuheng Dong、Yao Yuan、Xiaoshuang Gao、Miladili Keranmu、Wanfang Li、Xiaomin Xie、Zhaoguo Zhang

  DOI：10.1021/acs.orglett.8b02463

  日期：2018.9.21

  conditions. A 5.0 mmol scale dearomatization reaction proceeded smoothly with 95% yield even when the catalyst loading was reduced to 0.1 mol %, suggesting that this method was suitable for large-scale synthesis.

  可见光诱导的2-溴-1,3-二羰基化合物和炔烃的光催化分子间脱芳香环化反应，在温和的反应条件下，通过5-exo-dig自由基环化反应，以中等至良好的产率提供了生物学上重要的螺碳环结构。即使将催化剂的载量降低至0.1mol％，5.0mmol规模的脱芳香化反应也能以95％的收率顺利进行，表明该方法适用于大规模合成。
• Antiviral ethers of aspartate protease substrate isosteres
  申请人：Ciba-Geigy Corporation

  公开号：US05663200A1

  公开（公告）日：1997-09-02

  Antiretroviral compounds (which are effective, for example, against HIV) of the formula I ##STR1## in which R.sub.1 is an acyl radical lower-alkoxyl-lower-alkanoyl whose lower alkoxy radical is unsubstituted or is substituted by halogen, phenyl, lower alkoxy or a heterocyclic radical selected from piperidinyl, pyrrolidinyl, tetrahydropyranyl, tetrahydrofuranyl, thiazolidinyl, thiazolyl, indolyl or 4H-1-benzopyranyl which is unsubstituted or substituted by oxo, hydroxyl, amine, lower alkyl, lower-alkoxycarbonyl and/or phenyl-lower-alkoxycarbonyl; lower alkanoyl which is unsubstituted or is substituted by one of the said unsubstituted or substituted heterocyclic radicals; arylcarbonyl or heterocyclylcarbonyl which are substituted by heterocyclyl or heterocyclyl-lower-alkyl; phenyl-lower-alkanoyl which is substituted by hydroxyl and lower alkyl; or arylsulfonyl; or the residue of an amino acid which is defined in accordance with the description (and which may be acylated on the amino nitrogen by one of the abovementioned acyl radicals); R.sub.2 and R.sub.3 are in each case cyclohexyl, cyclohexenyl, phenyl, naphthyl or tetrahydronaphthyl which are unsubstituted or substituted by lower alkyl, phenyl, cyanophenyl, phenyl-lower-alkyl, halogen, halo-lower-alkyl, cyano, hydroxyl, lower alkoxy, phenyl-lower-alkoxyl, pyridyl-lower-alkoxy, lower-alkoxy-lower-alkoxy, lower-alkoxycarbonyl-lower-alkoxy, carboxyl-lower-alkoxy, hydroxyl-lower-alkoxy, carbamoyl-lower-alkoxy, cyano-lower-alkoxy, and phenyl-lower-alkanesulfonyl which is unsubstituted or substituted by halogen; R.sub.4 is lower alkyl, cyclohexyl or phenyl; and R.sub.5 is lower alkyl; and n is 1 or 2, or salts thereof, are novel.

  式I中的抗逆转录病毒化合物（例如针对HIV有效）## STR1 ##其中R.sub.1是酰基较低的烷氧基较低的酰基，其较低的烷氧基未取代或被卤素，苯基，较低的烷氧基或从哌啶基，吡咯烷基，四氢吡喃基，四氢呋喃基，噻唑烷基，噻唑基，吲哚基或未取代或取代为氧代，羟基，氨基，较低的烷基，较低的烷氧羰基和/或苯基-较低的烷氧羰基选择的杂环基团取代；未取代或取代为上述未取代或取代的杂环基团之一的未取代或取代的较低烷酰基；被杂环基或杂环基较低烷基取代的苯基羰基或杂环基羰基；被羟基和较低烷基取代的苯基较低烷酰基；或苯基磺酰基；或根据描述定义的氨基酸残基（并且可以通过上述酰基之一在氨基氮上酰化）；R.sub.2和R.sub.3分别是未取代或取代的环己基，环己烯基，苯基，萘基或四氢萘基，其未取代或被较低烷基，苯基，氰基苯基-较低烷基，卤素，卤代较低烷基，氰基，羟基，较低烷氧基，苯基-较低烷氧基，吡啶基-较低烷氧基，较低烷氧基-较低烷氧基，较低烷氧基羰基-较低烷氧基，羧基-较低烷氧基，羟基-较低烷氧基，氨基甲酰-较低烷氧基，氰基-较低烷氧基和未取代或取代为卤素的苯基-较低烷基磺酰基；R.sub.4是较低的烷基，环己基或苯基；而R.sub.5是较低的烷基；n为1或2，或其盐，是新颖的。
• Shoesmith; Rubli, Journal of the Chemical Society, 1927, p. 3104
  作者：Shoesmith、Rubli

  DOI：——

  日期：——
• Thienopyrimidinone Based Sirtuin-2 (SIRT2)-Selective Inhibitors Bind in the Ligand Induced Selectivity Pocket
  作者：Sandeep Sundriyal、Sébastien Moniot、Zimam Mahmud、Shang Yao、Paolo Di Fruscia、Christopher R. Reynolds、David T. Dexter、Michael J. E. Sternberg、Eric W.-F. Lam、Clemens Steegborn、Matthew J. Fuchter

  DOI：10.1021/acs.jmedchem.6b01690

  日期：2017.3.9

  Sirtuins (SIRTs) are NAD-dependent deacylases, known to be involved in a variety of pathophysiological processes and thus remain promising therapeutic targets for further validation. Previously, we reported a novel thienopyrimidinone SIRT2 inhibitor with good potency and excellent selectivity for SIRT2. Herein, we report an extensive SAR study of this chemical series and identify the key pharmacophoric elements and physiochemical properties that underpin the excellent activity observed. New analogues have been identified with submicromolar SIRT2 inhibtory activity and good to excellent SIRT2 subtype-selectivity. Importantly, we report a cocrystal structure of one of our compounds (29c) bound to SIRT2. This reveals our series to induce the formation of a previously reported selectivity pocket but to bind in an inverted fashion to what might be intuitively expected. We believe these findings will contribute significantly to an understanding of the mechanism of action of SIRT2 inhibitors and to the identification of refined, second generation inhibitors.