methyl 6-(benzyloxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylate | 161454-24-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 6-(benzyloxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• 英文别名: methyl 6-phenylmethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate
• CAS: 161454-24-6；161454-25-7；171499-23-3
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: UYYYXEXMVFBJDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 6-(benzyloxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到(+/-)-[6-(benzyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]methanol
  参考文献：
  名称：

  Reversible Competitive α-Ketoheterocycle Inhibitors of Fatty Acid Amide Hydrolase Containing Additional Conformational Constraints in the Acyl Side Chain: Orally Active, Long-Acting Analgesics

  摘要：

  A series of alpha-ketooxazoles containing conformational constraints in the C2 acyl side chain of 2 (OL-135) were examined as inhibitors of fatty acid amide hydrolase (FAAH). Only one of the two possible enantiomers displayed potent FAAH inhibition (S vs R enantiomer), and their potency is comparable or improved relative to 2, indicating that the conformational restriction in the C2 acyl side chain is achievable. A cocrystal X-ray structure of the alpha-ketoheterocycle 12 bound to a humanized variant of rat FAAH revealed its binding details, confirmed that the (S)-enantiomer is the bound active inhibitor, shed light on the origin of the enantiomeric selectivity, and confirmed that the catalytic Ser241 is covalently bound to the electrophilic carbonyl as a deprotonated hemiketal. Preliminary in vivo characterization of the inhibitors 12 and 14 is reported demonstrating that they raise brain anandamide levels following either intraperitoneal (ip) or oral (po) administration indicative of effective in vivo FAAH inhibition. Significantly, the oral administration of 12 caused dramatic accumulation of anandamide in the brain, with peak levels achieved between 1.5 and 3 h, and these elevations were maintained over 9 h. Additional studies of these two representative members of the series (12 and 14) in models of thermal hyperalgesia and neuropathic pain are reported, including the demonstration that 12 administered orally significantly attenuated mechanical (> 6 h) and cold (> 9 h) allodynia for sustained periods consistent with its long-acting effects in raising the endogenous concentration of anandamide.

  DOI：

  10.1021/jm101597x
• 作为产物：
  描述：

  1,2,3,4-四氢-6-羟基-2-萘羧酸 在 硫酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 反应 18.0h， 生成 methyl 6-(benzyloxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylate
  参考文献：
  名称：

  [EN] ALPHA-KETOHETEROCYCLES AND METHODS OF MAKING AND USING
  [FR] ALPHA-CÉTOHÉTÉROCYCLES ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION

  摘要：

  抑制脂肪酸酰胺水解酶的有效化合物已被披露，该酶负责代谢内源大麻素如阿南胺。这些化合物可用作镇痛化合物和诱导睡眠的化合物，可经口服给药，并具有相对较长的作用持续时间。还提供了这些化合物的制备方法。这些化合物是杂环酮的构象约束类似物，如噁唑基酮。

  公开号：

  WO2012106569A1

文献信息

• ALPHA-KETOHETEROCYCLES AND METHODS OF MAKING AND USING
  申请人：Boger Dale L.

  公开号：US20130338196A1

  公开（公告）日：2013-12-19

  Compounds are disclosed that are effective in inhibition of fatty acid amide hydrolase, an enzyme responsible for catabolism of endogenous cannabinoids such as anandamide. The compounds are useful as analgesic compounds and as sleep-inducing compounds, that can be orally administered, and that can have a relatively long duration of effect. Methods of preparation of the compounds are also provided. The compounds are conformationally constrained analogs of heterocyclylketones such as oxazolylketones.

  本文披露了一些化合物，这些化合物能够有效地抑制脂肪酸酰胺水解酶，这种酶负责代谢内源性大麻素如阿那酰胺。这些化合物可用作镇痛化合物和催眠化合物，可以口服，并具有相对较长的作用时间。本文还提供了制备这些化合物的方法。这些化合物是杂环羰基酮（如噁唑基酮）的构象限制类似物。
• Liquid crystal material, liquid crystal composition and liquid crystal element
  申请人：MITSUI PETROCHEMICAL INDUSTRIES, LTD.

  公开号：EP0617109A1

  公开（公告）日：1994-09-28

  Disclosed is a liquid crystal material represented by the following formula [I]:         R-X-A¹-Y¹-A²- (Y²-A³)n-Z-R*   [I] wherein R is an alkyl or polyfluoroalkyl group; X is a group such as -COO-, or a single bond; n is 0 or 1; A¹, A² and A³ are each a cyclic group such as tetralin, and at least one of them has an optically active group; Y¹ and Y² are each a group such as -COO-; Z is a group such as -O-, or a single bond; and R* is an optically active group. Also disclosed are a liquid crystal composition comprising the liquid crystal material represented by the above formula, and a liquid crystal element in which the liquid crystal material is used. The liquid crystal material of the invention shows excellent liquid crystal characteristics because it has at least two optically active groups.

  本发明公开了由下式[I]表示的液晶材料： R-X-A¹-Y¹-A²- (Y²-A³)n-Z-R* [I]. 其中 R 是烷基或多氟烷基；X 是-COO-等基团或单键；n 是 0 或 1；A¹、A² 和 A³ 分别是四氢萘等环状基团，且其中至少一个具有光学活性基团；Y¹ 和 Y² 分别是-COO-等基团；Z 是-O-等基团或单键；以及 R* 是光学活性基团。本发明还公开了一种液晶组合物，该组合物包含由上式表示的液晶材料，以及一种使用了该液晶材料的液晶元件。本发明的液晶材料具有至少两个光学活性基团，因此具有优异的液晶特性。
• JPH07224005A
  申请人：——

  公开号：JPH07224005A

  公开（公告）日：1995-08-22
• US5422039A
  申请人：——

  公开号：US5422039A

  公开（公告）日：1995-06-06
• US9504675B2
  申请人：——

  公开号：US9504675B2

  公开（公告）日：2016-11-29