8-苄氧基-1-萘满酮 | 88058-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 8-苄氧基-1-萘满酮
• 英文名称: 8-benzyloxy-1,2,3,4-tetrahydro-1-naphthalenone
• 英文别名: 8-Phenylmethoxytetralone；8-benzyloxy-1,2,3,4-tetrahydro-naphthalen-1-one；8-(Benzyloxy)-3,4-dihydronaphthalen-1(2H)-one；8-phenylmethoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 88058-45-1
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: FHXGYNYDJHICOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-苄氧基-1-萘满酮 在 potassium tert-butylate 、 亚硝酸异戊酯 作用下， 以 乙醚 、 正丁醇 为溶剂， 反应 4.0h， 生成 8-Benzyloxy-3,4-dihydro-[1,2]naphthoquinone 2-oxime
  参考文献：
  名称：

  Synthesis of 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, a new class of dopamine agonists

  摘要：

  A series of tricyclic oxazines, namely, the 4-substituted 2H-naphth[1,2-b]-1,4-oxazines, have been synthesized and assayed for dopamine agonist activity. One of the members of this series, compound (+)VII-15, was found to be a remarkably potent agonist in vivo when tested in the standard 6-hydroxydopamine lesioned rat assay. The absolute configuration of the compound corresponds to that found in the active isomer of apomorphine. Its activity at the alpha 2 receptor (vs. [3H]clonidine) is relatively low. It also failed to stimulate the synthesis of cAMP in the carp retina assay, thus giving the compound a highly selective profile in favor of the D2 receptor.

  DOI：

  10.1021/jm00378a014
• 作为产物：
  描述：

  1,8-二羟基萘 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~60.0 ℃ 、344.75 kPa 条件下， 反应 20.0h， 生成 8-苄氧基-1-萘满酮
  参考文献：
  名称：

  [EN] BICYCLIC PHENOL COMPOUNDS AND USE THEREOF
  [FR] COMPOSÉS PHÉNOLIQUES BICYCLIQUES ET LEUR UTILISATION
  [ZH] 双环苯酚类化合物及其应用

  摘要：

  一系列苯酚类化合物及其应用，具体公开了式(III)所示化合物及其药学上可接受的盐。

  公开号：

  WO2022194278A1

文献信息

• Photocyclization reactions. Part<b>3</b>. Synthesis of naphtho[1,8-<i>bc</i>]-furans and Cyclohepta[<i>cd</i>]benzofurans using photocyclization of 8-alkoxy-1,2,3,4-tetrahydro-1-naphthalenones and 4-alkoxy-6,7,8,9-tetrahydro-5<i>H</i>-benzocyclohepten-5-ones
  作者：Essam Mohamed Sharshira、Haruki Iwanami、Mutsuo Okamura、Eietsu Hasegawa、Takaaki Horaguchi

  DOI：10.1002/jhet.5570330104

  日期：1996.1

  Photocyclization reactions were carried out on 8-alkoxy-1,2,3,4-tetrahydro-1-naphthalenones (six-membered ring ketones) 4a-g and 4-alkoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ones (seven-membered ring ketones) 5a-e in acetonitrile. Irradiation of 4a-f gave rearranged naphthyl alcohols 8a-f as major products. In the case of 4g, 2a,3,4,5-tetrahydronaphtho[1,8-bc]furan-2a-ol 6g was obtained. In contrast

  在8-烷氧基-1,2,3,4-四氢-1-萘酮（六元环酮）4a-g和4-烷氧基-6,7,8,9-四氢-5 H上进行光环化反应-乙腈中的-苯并环庚烯5-酮（七元环酮）5a -e。辐照4a-f得到重排的萘醇8a-f作为主要产物。在4g的情况下，获得2g，3a，3，4，5-四氢萘并[1，8 - bc ]呋喃-2a-ol 6g。相反，辐照5a -e以良好的产率得到了2,2a，3,4,5,6-六氢环庚[ cd ]苯并呋喃-2a -ols 9a-e。之间的反应性差异4a-g和5a-e归因于六元和七元环的构象。讨论了1，5-双自由基的环化步骤中的构象和取代基效应以及反应途径。
• Octahydrophenanthrene derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US05385947A1

  公开（公告）日：1995-01-31

  Compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 each individually are hydrogen or lower alkyl optionally substituted by aryl or C.sub.3-6 -cycloalkyl; R.sup.4 and R.sup.5 either both are hydrogen or both are halogen or one is hydrogen and the other is halogen, hydroxy, lower alkoxy, aryloxy or amino; and R.sup.3 is hydrogen or, where no primary or secondary amino group is present, alkanoyl; with the proviso that all the groups R.sup.1 through R.sup.5 cannot simultaneously be hydrogen; as well as pharmaceutically acceptable salts of compounds of formula I with acids have valuable pharmacodynamic properties as non-competitive NMDA antagonists and can accordingly be used as neuroprotectives.

  具有以下结构的化合物：##STR1## 其中R.sup.1和R.sup.2各自为氢或辅以芳基或C.sub.3-6-环烷基的低烷基; R.sup.4和R.sup.5要么都是氢，要么都是卤素，或者一个是氢另一个是卤素、羟基、低烷氧基、芳氧基或氨基; R.sup.3是氢或者在没有一级或二级氨基团的情况下是烷酰基; 但是要注意，所有的基团R.sup.1到R.sup.5不能同时为氢；以及具有药用酸盐的I式化合物具有有价值的药理作用性质，作为非竞争性NMDA拮抗剂，并因此可用作神经保护剂。
• Synthesis and aldose reductase inhibitory activity of a new series of benzo[h]cinnolinone derivatives
  作者：Luca Costantino、Giulio Rastelli、Giorgio Cignarella、Daniela Barlocco

  DOI：10.1016/s0014-827x(00)00035-5

  日期：2000.8

  Following our previous studies on pyridazinone carboxylic acids as potent and selective aldose reductase (ALR2) inhibitors, a new series of benzo[h]cinnolinone carboxylic acids, variously substituted at the positions 4, 7-10 and differently modified both at the central ring and at the acidic side chain, were synthesized and tested as inhibitors of ALR2. Comparison with previously synthesized compounds

  继我们先前对哒嗪酮羧酸作为有效和选择性醛糖还原酶（ALR2）抑制剂的研究之后，一系列新的苯并[h]肉桂醇酮羧酸系列分别在4、7-10位取代，并且在中心环和合成并测试了酸性侧链上的A1作为ALR2的抑制剂。与先前合成的化合物进行比较可以使我们为此类化合物更精确地定义构效关系。实际上，除了酸性侧链的重要性外，它们的性质还受到苯并[h]肉桂醇核上存在的取代基的强烈影响，其效力范围从索比尼尔到非常弱的活性化合物。
• Enantioselective Ruthenium-Catalyzed Benzocyclobutenone–Ketol Cycloaddition: Merging C–C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction
  作者：Brett R. Ambler、Ben W. H. Turnbull、Sankar Rao Suravarapu、Maulen M. Uteuliyev、Nancy O. Huynh、Michael J. Krische

  DOI：10.1021/jacs.8b05724

  日期：2018.7.25

  The first enantioselective intermolecular metal-catalyzed cycloadditions of benzocyclobutenones via C-C bond oxidative addition are described. In the presence of a ruthenium(0) complex modified by ( R)-DM-SEGPHOS, tetralone-derived ketols and benzocyclobutenones combine to form cycloadducts with complete regio- and diastereoselectivity and high enantioselectivity. Using this method, the "bay region"

  描述了苯并环丁烯酮通过 CC 键氧化加成的第一个对映选择性分子间金属催化环加成。在 (R)-DM-SEGPHOS 修饰的钌 (0) 络合物存在下，四氢萘酮衍生的酮醇和苯并环丁烯酮结合形成具有完全区域和非对映选择性以及高对映选择性的环加合物。利用该方法制备了安古环素天然产物沙霉素的“湾区”亚结构。
• Conformational effects in photocyclization of six and seven-membered ring alkoxyketones
  作者：Takaaki Horaguchi、Haruki Iwanami、Takakazu Tanaka、Eietsu Hasegawa、Takahachi Shimizu

  DOI：10.1039/c39910000044

  日期：——

  Irradiation of 8-alkoxytetrahydro-1-naphthalenones 5 gave rearranged naphthyl alcohols 11 as major products and in contrast, 4-alkoxytetrahydrobenzocyclohepten-5-ones 6 afforded tetrahydrocyclohepta[cd]benzofurans 14 in good yields; the difference in reactivities is attributed to the conformation of six- and seven-membered rings.

  辐照 8-烷氧基四氢-1-萘酮 5 得到重排萘醇 11 作为主要产物，与此相反，4-烷氧基四氢苯并环庚烯-5-酮 6 以良好的产率得到四氢环庚烷并[cd]苯并呋喃 14；反应活性的差异归因于六元环和七元环的构象。

表征谱图