1,2,3,4-Tetrahydro-6-methoxy-2-naphthalenemethanol | 88285-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-Tetrahydro-6-methoxy-2-naphthalenemethanol
• 英文别名: (6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methanol；6-methoxy-1,2,3,4-tetrahydro-2-naphthylmethyl alcohol；7-methoxy-1,2,3,4-tetrahydronaphthalen-3-ylmethanol；6-methoxy-1,2,3,4-tetrahydro-2-naphthalenemethanol；2-hydroxymethyl-6-methoxytetralin
• CAS: 88285-44-3
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: BZBOEUSIJFUBKT-UHFFFAOYSA-N

物化性质

• 沸点：
  332.4±35.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-Tetrahydro-6-methoxy-2-naphthalenemethanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以79%的产率得到6-甲氧基-1,2,3,4-四氢-萘-2-甲醛
  参考文献：
  名称：

  在氧化还原标记过程中探测分子内电子转移

  摘要：

  在这里，我们表明，氧化还原标记引导的分子间形式的[2 + 2]环加成可以用作探针，以研究分子内单电子转移（SET）的机制。分子内SET的功效可与伴随的碳-碳键形成和/或裂解，从而导致环加成或交叉复分解一起评估。实验和理论结果表明，分子内SET受热力学和动力学控制，并且还可以通过键发生，不仅通过空间发生。

  DOI：

  10.1021/acs.orglett.9b02808
• 作为产物：
  描述：

  6-Methoxy-2-hydroxymethylen-1-tetralon 在 三氟化硼乙醚 、 硼烷-叔丁基胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到1,2,3,4-Tetrahydro-6-methoxy-2-naphthalenemethanol
  参考文献：
  名称：

  在氧化还原标记过程中探测分子内电子转移

  摘要：

  在这里，我们表明，氧化还原标记引导的分子间形式的[2 + 2]环加成可以用作探针，以研究分子内单电子转移（SET）的机制。分子内SET的功效可与伴随的碳-碳键形成和/或裂解，从而导致环加成或交叉复分解一起评估。实验和理论结果表明，分子内SET受热力学和动力学控制，并且还可以通过键发生，不仅通过空间发生。

  DOI：

  10.1021/acs.orglett.9b02808

文献信息

• Synthesis and biological activities of 3-aminomethyl-1,2-dihydronaphthalene derivatives.
  作者：KATSUMI ITOH、AKIO MIYAKE、MASAO TANABE、MINORU HIRATA、YOSHIKAZU OKA

  DOI：10.1248/cpb.31.2006

  日期：——

  A series of 3-aminomethyl-1, 2-dihydronaphthalene derivatives (6-22) was prepared from the corresponding 3, 4-dihydro-1 (2H)-naphthalenone derivatives (24a-q) in three steps, namely the Mannich reaction, reduction of the carbonyl group with sodium borohydride, and dehydration with ethanolic hydrogen chloride. Compounds 6-22 and several related analogs (23, 27-30) were tested for vasodilating and antihypertensive activities. Potent cerebral vasodilating and antihypertensive activities were exhibited by 1-benzhydryl-4-(7-disubstituted amino-1, 2-dihydro-3-naphthyl) methylpiperazines (16, 18 and 19).

  一系列3-氨基甲基-1,2-二氢萘衍生物（6-22）通过三步反应从相应的3,4-二氢-1(2H)-萘酚酮衍生物（24a-q）制备得到，这三步反应分别是曼尼希反应、用硼氢化钠还原羰基和用乙醇氢氯酸脱水。化合物6-22及其相关类似物（23, 27-30）被测试了血管舒张和抗高血压活性。1-二苯甲基-4-(7-二取代氨基-1,2-二氢-3-萘基)甲基哌嗪（16,18和19）展现了强大的脑部血管舒张和抗高血压活性。
• Farnesylated tetrahydro-naphthalenols as hypolipidemic agents
  申请人：Bristol-Myers Squibb Company

  公开号：US05204373A1

  公开（公告）日：1993-04-20

  The invention relates to novel farnesylated tetrahydro-naphthalenols, that inhibit HMGR activity which results in a decrease in serum total cholesterol, a decrease in LDL cholesterol levels, and inhibition of LDL oxidation. The farnesylated tetrahydro-naphthalenols of the present invention are thus useful for cholesterol/lipid lowering in cases of hypercholesterolemia, hyperlipidemia, and atherosclerosis.

  该发明涉及一种新型的韦尼基化四氢萘酚，它抑制HMGR活性，导致血清总胆固醇降低，LDL胆固醇水平降低，以及抑制LDL氧化。因此，本发明的韦尼基化四氢萘酚在高胆固醇血症、高脂血症和动脉粥样硬化病例中用于降低胆固醇/脂质是有用的。
• Amine compounds, their production and use
  申请人：——

  公开号：US20040077867A1

  公开（公告）日：2004-04-22

  A compound of the formula: 1 wherein Ar is an aromatic ring assembly group which may be substituted or a fused aromatic group which may be substituted; X is (i) a bond, (ii) —S—, —SO— or —SO 2 —, (iii) C 1-6 alkylene, C 2-6 alkenylene or C 2-6 alkynylene, etc., (iv) —CO—O— or (v) —(CH 2 )p-X 1 —, —(CH 2 )p-X 1 —CH 2 )q-, —(CH 2 )r-CO—X 1 —, —SO 2 —NR 8 — or —(CH 2 )r-SO 2 —NR 8 — wherein X 1 is O or NR 8 , R 8 is H, a hydrocarbon group which may be substituted or an acyl, p is 0 to 5, q is 1 to 5, p+q is 1 to 5, and r is 1 to 4; Y is a divalent C 1-6 aliphatic hydrocarbon group optionally containing O or S, which may be substituted; R 1 and R 2 each is H or a lower alkyl which may be substituted, or R 1 and R 2 form a N-containing heterocyclic ring which may be substituted; Ring A is a benzene ring which may be further substituted; and Ring B is a 4- to 8-membered ring which may be further substituted, or a salt thereof has the effect of inhibiting amyloid-&bgr; protein production and/or secretion and is useful as a pharmaceutical composition for preventing and/or treating the neurodegenerative disease, etc.

  化合物的公式为1，其中Ar是芳香环组装基团，可以是取代的或融合的芳香族基团，X是(i)键，(ii) -S-, -SO-或-SO2-, (iii) C1-6烷基，C2-6烯基或C2-6炔基等，(iv) -CO-O-或(v) -(CH2)p-X1-，-(CH2)p-X1-CH2)q-，-(CH2)r-CO-X1-，-SO2-NR8-或-(CH2)r-SO2-NR8-其中X1是O或NR8，R8是H，可以是取代的碳氢基团或酰基，p为0至5，q为1至5，p+q为1至5，r为1至4；Y是二价的C1-6脂肪烃基团，可以包含O或S，可以是取代的；R1和R2分别是H或可以取代的低碳烷基，或R1和R2形成一个可以取代的含氮杂环；环A是苯环，可以进一步取代；环B是4-至8成员环，可以进一步取代，或其盐具有抑制淀粉样-β蛋白产生和/或分泌的作用，并且作为预防和/或治疗神经退行性疾病的药物组成物有用。
• 4-hydroxy-piperidine derivatives
  申请人：Hoffmann-La Roche Inc.

  公开号：US06359138B1

  公开（公告）日：2002-03-19

  The present invention relates to 4-hydroxy-piperidine derivatives of the general formula wherein X denotes —O—, —NH—, —CH2—, —CH═, —CHOH—, —CO—, —S—, —SO— or —SO2—; R1-R4 are, independently from each other, hydrogen, hydroxy, lower-alkyl-sulfonylamino, 1- or 2-imidazolyl or acetamido; R5-R8 are, independently from each other, hydrogen, hydroxy, lower-alkyl, halogen, lower-alkoxy, trifluoromethyl or trifluoromethyloxy; a and b may be a double bond, provided that when “a” is a double bond, “b” cannot be a double bond; n is 0-2; m is 1-3; p is 0 or 1 and to pharmaceutically acceptable addition salts thereof. Compounds of the present invention are NMDA(N-methyl-D-aspartate)-receptor subtype selective blockers, which can be used in mediating processes underlying development of CNS including learning and memory formation and function.

  本发明涉及一般式的4-羟基哌啶衍生物，其中X表示-O-，-NH-，-CH2-，-CH═，-CHOH-，-CO-，-S-，-SO-或-SO2-;R1-R4独立地表示氢、羟基、较低烷基磺酰胺、1-或2-咪唑基或乙酰胺基;R5-R8独立地表示氢、羟基、较低烷基、卤素、较低烷氧基、三氟甲基或三氟甲氧基;a和b可以是双键，但是当“a”是双键时，“b”不能是双键;n为0-2;m为1-3;p为0或1，并且其药学上可接受的盐。本发明化合物是NMDA（N-甲基-D-天门冬氨酸）受体亚型选择性阻滞剂，可用于调节中枢神经系统发育过程，包括学习和记忆形成和功能。
• Synthesis and Structure−Activity Relationships of 1-Aralkyl-4-Benzylpiperidine and 1-Aralkyl-4-Benzylpiperazine Derivatives as Potent σ Ligands
  作者：Luca Costantino、Francesca Gandolfi、Claudia Sorbi、Silvia Franchini、Orazio Prezzavento、Franco Vittorio、Giuseppe Ronsisvalle、Amedeo Leonardi、Elena Poggesi、Livio Brasili

  DOI：10.1021/jm049433t

  日期：2005.1.1

  In the attempt to define more accurately structure-affinity relationships for sigma(1) and sigma(2) ligands, we synthesized and tested on sigma subtype receptors a series of aralkyl derivatives of 4-benzylpiperidine, in which the effect of modifications on the aralkyl moiety was studied in a systematic way. The affinity of the compounds here described varied to a great extent, with a sigma(2)/sigma(1), selectivity ranging from 0.1 to 9. Thus, to confirm the ability of the piperazine derivative to bind to sigma(1) receptors in a different way than piperidines, we synthesized and tested a series of piperazine compounds; the comparison of their affinity with that of the corresponding piperidines strongly supports the possibility of a different binding mode. While the compounds here described are on the whole selective for a vs serotonin 5-HT1A and dopamine D-2 receptors, 9aa, 9ba and 9ab possess a remarkable affinity for both a and 5-HT1A receptors, with K-i in the nanomolar range, and are selective with respect to D2 receptors. They displayed also a partial agonist profile in a human 5-HT1A [S-35]GTPgammaS binding assay, suggesting their potential use as atypical antipsychotic agents.