8-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid | 74145-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 8-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid
• 英文别名: 1-Naphthalenecarboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-
• CAS: 74145-11-2
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: IWKURRAOVBDUMT-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMF；二甲基亚砜；

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid 在 palladium on activated charcoal manganese(IV) oxide 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 5,6,7,8-四氢萘-1-甲醛
  参考文献：
  名称：

  光化学生成的双环邻喹啉甲烷：双环醛和酮的光烯化

  摘要：

  研究了双环邻喹啉二甲烷的光烯化路线。首次以分子间方式将双环光烯醇与各种亲二烯体一起捕获。通过从1-茚满醇，α-四醇和1-苯并亚砜开始的选择性路线制备所有邻-喹二甲烷前体。辐照提供了E-单独捕获具有相同效率的-光烯醇，但其衍生自茚满-4-羧醛。这种低效率归因于醛快速自氧化为羧酸。与本研究中的其他醛相比，苯并suberan-9-羧醛的光烯醇与富马酸二甲酯之间反应的面部选择性要低得多。由七元环的存在引起的扭曲的二烯解释了这些结果。

  DOI：

  10.1016/s0040-4020(97)10068-0
• 作为产物：
  描述：

  1,2,3,4-四氢-1-萘酚 在 正丁基锂 、 四甲基乙二胺 作用下， 以 正戊烷 为溶剂， 反应 9.0h， 生成 8-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid
  参考文献：
  名称：

  Meyer, Norbert; Seebach, Dieter, Chemische Berichte, 1980, vol. 113, # 4, p. 1304 - 1319

  摘要：

  DOI：

文献信息

• Supramolecular Control of Selectivity in Hydroformylation of Vinyl Arenes: Easy Access to Valuable β-Aldehyde Intermediates
  作者：Paweł Dydio、Joost N. H. Reek

  DOI：10.1002/anie.201209582

  日期：2013.4.2

  flow! A rationally designed regioselective hydroformylation catalyst, [Rh/L], in which noncovalent ligand–substrate interactions allow the unprecedented reversal of selectivity from the typical α‐aldehyde to the otherwise unfavored product β‐aldehyde, is reported. This catalytic system opens up novel and sustainable synthetic pathways to important intermediates for the fine‐chemicals industry.

  逆流而上！据报道，一种合理设计的区域选择性加氢甲酰化催化剂[Rh / L]，其中非共价配体-底物的相互作用使选择性从典型的α-醛到其他不利的产物β-醛发生了前所未有的逆转。该催化体系为精细化工行业的重要中间体开辟了新的，可持续的合成途径。
• [EN] 4-SUBSTITUTED IMIDAZOLE-2-THIONES AND IMIDAZOL-2-ONES AS AGONISTS OF THE ALPHA-2B AND ALPHA-2C ADRENERGIC RECEPTORS<br/>[FR] IMIDAZOLE-2-ONES ET IMIDAZOLE-2-THIONES 4 SUBSTITUES COMME AGONISTES DES ADRENO-RECEPTEURS ALPHA-2B ET ALPHA-2C
  申请人：ALLERGAN INC

  公开号：WO2003099795A1

  公开（公告）日：2003-12-04

  Compounds of Formula (I): where X is S and the variables have the meaning defined in the specification are specific or selective to alpha2B and/or alpha2C adrenergic receptors in preference over alpha2A adrenergic receptors, and as such have no or only minimal cardivascular and/or sedatory activity. These compounds of Formula (I) are useful as medicaments in mammals, including humans, for treatment of diseases and or alleviations of conditions which are responsive to treatment by agonists of alpha2B adrenergic receptors. Compounds of Formula (I) where X is O also have the advantageous property that they have no or only minimal cardivascular and/or sedatory activity and are useful for treating pain and other conditions with no or only minimal cardivascular and/or sedatory activity.

  式(I)的化合物：其中X为S，变量的含义如规范中定义的那样，对alpha2B和/或alpha2C肾上腺素受体具有特异性或选择性，优先于alpha2A肾上腺素受体，并且因此具有无或仅有极小的心血管和/或镇静活性。这些式(I)的化合物在哺乳动物，包括人类中，作为药物用于治疗对alpha2B肾上腺素受体激动剂治疗有响应的疾病和/或缓解症状是有用的。式(I)的化合物，其中X为O，还具有有利的特性，即它们具有无或仅有极小的心血管和/或镇静活性，并且适用于治疗无或仅有极小的心血管和/或镇静活性的疼痛和其他症状。
• A solid state NMR and X-ray crystallographic investigation of dynamic disorder in solid tetrahydronaphthalene derivatives
  作者：Glenn A. Facey、Terrence J. Connolly、Corinne Bensimon、Tony Durst

  DOI：10.1139/v96-206

  日期：1996.10.1

  The solid state disorder of two tetrahydronaphthalene derivatives, N-methyl-N-methoxy-5,6,7,8-tetrahydro-1-naphthamide and 5,6,7,8-tetrahydro-1-naphthoic acid, was studied by solid state NMR and single crystal X-ray diffraction. The X-ray crystal structure of N-methyl-N-methoxy-5,6,7,8-tetrahydro-1-naphthamide was obtained at 123 K. It indicated the presence of two distinct molecular conformations. Solid state ¹³C CP/MAS NMR data using the dipolar dephasing technique revealed that the two conformations of the molecule are dynamically disordered, while solid state ²H NMR data, collected on a specifically deuterated analog, were used to determine the populations of each conformation as well as an apparent activation energy. Solid state NMR experiments were also used to show that 5,6,7,8-tetrahydro-1-naphthoic acid possesses the same type of dynamic disorder. Key words: deuterium NMR, solid state NMR, dynamic disorder. X-ray, tetrahydronaphthalene derivatives

  两个四氢萘衍生物，N-甲基-N-甲氧基-5,6,7,8-四氢-1-萘酰胺和5,6,7,8-四氢-1-萘甲酸的固态无序性通过固态NMR和单晶X射线衍射进行了研究。N-甲基-N-甲氧基-5,6,7,8-四氢-1-萘酰胺的X射线晶体结构在123K时获得。它表明存在两种不同的分子构象。使用偶极耦合去相位技术的固态¹³C CP/MAS NMR数据显示分子的两种构象是动态无序的，而在特定氘代物上收集的固态²H NMR数据用于确定每种构象的种群以及表观活化能。固态NMR实验还表明5,6,7,8-四氢-1-萘甲酸具有相同类型的动态无序性。关键词：氘NMR，固态NMR，动态无序。X射线，四氢萘衍生物
• The synthesis of bicyclic ortho-quinodimethanes from tricyclic sulfones
  作者：Terrence J. Connolly、Tony Durst

  DOI：10.1016/s0040-4020(97)10066-7

  日期：1997.11

  The first synthesis of bicyclic ortho-quinodimethanes from tricyclic sulfone precursors has been achieved. The required sulfones, 3,4,5,6-tetrahydro-1H-cyclohex[cd]benzothiophene-2,2-dioxide and 1,3,4,5,6,7-hexahydrocyclohept[cd]benzothiophene-2,2-dioxide, were prepared from α-tetralone and benzosuberone utilizing a ring closure proceeding through a sulfonium salt intermediate. The same strategy failed

  已经实现了从三环砜前体的第一合成双环邻-喹二甲烷。所需的砜，3,4,5,6-四氢-1H-环己[cd]苯并噻吩-2,2-二氧化物和1,3,4,5,6,7-六氢环庚[cd]苯并噻吩-2,2-使用闭环通过α盐中间体，由α-四氢萘酮和苯并亚砜制备二氧化碳。尝试制备茚满系列的三环砜时，相同的策略失败了。当比较三环醚化合物的能力和易形成性时，还发现了其他对比反应性。这些结果表明，后面的环形系统应变很大。
• 4-(SUBSTITUTED CYCLOALKYLMETHYL) IMIDAZOLE-2-THIONES, 4-(SUBSTITUTED CYCLOALKENYLMETHYL) IMIDAZOLE-2-THIONES, 4-(SUBSTITUTED CYCLOALKYLMETHYL) IMIDAZOL-2-ONES AND 4-(SUBSTITUTED CYCLOALKENYLMETHYL) IMIDAZOL-2-ONES AND RELATED COMPOUNDS
  申请人：Chow Ken

  公开号：US20070072926A1

  公开（公告）日：2007-03-29

  Compounds of Formula 1 where X is S and the variables have the meaning defined in the specification are specific or selective to alpha 2B and/or alpha 2C adrenergic receptors in preference over alpha 2A adrenergic receptors, and as such have no or only minimal cardivascular and/or sedatory activity. These compounds of Formula 1 are useful as medicaments in mammals, including humans, for treatment of diseases and or alleviations of conditions which are responsive to treatment by agonists of alpha 2B adrenergic receptors. Compounds of Formula 1 where X is O also have the advantageous property that they have no or only minimal cardivascular and/or sedatory activity and are useful for treating pain and other conditions with no or only minimal cardivascular and/or sedatory activity.

  式1中X为S且变量的含义已在说明书中定义，这些化合物具有特异性或选择性作用于α2B和/或α2C肾上腺素受体，而不是α2A肾上腺素受体，因此它们没有或仅有最小的心血管和/或镇静活性。这些式1的化合物可用作哺乳动物，包括人类的药物，用于治疗对α2B肾上腺素受体激动剂有反应的疾病和/或缓解条件。式1中X为O的化合物还具有优越的特性，即它们没有或仅有最小的心血管和/或镇静活性，可用于治疗无或仅有最小心血管和/或镇静活性的疼痛和其他病症。