1-methyl-3,4-dihydronaphthalene-2-carboxylic acid | 6279-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methyl-3,4-dihydronaphthalene-2-carboxylic acid
• 英文别名: 1-methyl-3,4-dihydro-[2]naphthoic acid；1-Methyl-3,4-dihydro-[2]naphthoesaeure；1-Methyl-3.4-dihydro-naphthalin-carbonsaeure-(2)；3,4-dihydro-1-methyl-2-naphthalenecarboxylic acid；1-Methyl 3,4-dihydro naphthalene 2-carboxylic acid；1-methyl-3,4-dihydro-2-naphtoic acid
• CAS: 6279-88-5
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: BIWORKOXNUWVKT-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C
• 沸点：
  315.2±21.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methyl-3,4-dihydronaphthalene-2-carboxylic acid 在 palladium on activated charcoal 、 lithium aluminium tetrahydride 、 乙醚 、 乙醇 作用下， 生成 (+/-)-(cis-1-Methyl-1,2,3,4-tetrahydro-[2]naphthyl)-methanol
  参考文献：
  名称：

  Julia; Bonnet, Bulletin de la Societe Chimique de France, 1959, p. 419

  摘要：

  DOI：
• 作为产物：
  描述：

  2-苯乙基乙酰乙酸乙酯 在 硫酸 、 水 作用下， 反应 4.0h， 以81%的产率得到1-methyl-3,4-dihydronaphthalene-2-carboxylic acid
  参考文献：
  名称：

  3,4-dihydro-2-naphthamide derivatives as selective dopamine D3 ligands

  摘要：

  该发明涉及公式(I)的3,4-二氢-2-萘酰胺衍生物，包含它们的药物组合物以及它们作为多巴胺D3受体的部分激动剂或拮抗剂在治疗神经心理障碍方面的治疗应用。

  公开号：

  EP1683790A1

文献信息

• EtAlCl₂/2,6-Disubstituted Pyridine-Mediated Carboxylation of Alkenes with Carbon Dioxide
  作者：Shinya Tanaka、Kota Watanabe、Yuuki Tanaka、Tetsutaro Hattori

  DOI：10.1021/acs.orglett.6b00918

  日期：2016.6.3

  and trialkyl-substituted alkenes undergo carboxylation with CO2 in the presence of EtAlCl2 and 2,6-dibromopyridine to afford the corresponding α,β- and/or β,γ-unsaturated carboxylic acids. This reaction is suggested to proceed via the electrophilic substitution of EtAlCl2 with the aid of the base, followed by the carbonation of the resulting ate complex. This reaction can be applied to terminal dialkylalkenes

  在EtAlCl 2和2,6-二溴吡啶的存在下，α-芳基烯烃和三烷基取代的烯烃与CO 2进行羧化反应，得到相应的α，β-和/或β，γ-不饱和羧酸。建议该反应通过在碱的辅助下对EtAlCl 2进行亲电取代，然后将所得的盐配合物碳酸化来进行。通过使用2，6-二叔丁基吡啶和2，6-二溴吡啶的混合物，该反应可用于末端二烷基烯烃。
• 3,4-dihydro-2-naphthamide derivatives as selective dopamine D3 ligands
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP1683790A1

  公开（公告）日：2006-07-26

  The invention relates to 3,4-dihydro-2-naphthamide derivatives of formula (I), pharmaceutical compositions containing them and their therapeutic applications as partial agonists or antagonists of the dopamine D3 receptor for the treatment of neuropsychological disorders.

  该发明涉及公式(I)的3,4-二氢-2-萘酰胺衍生物，包含它们的药物组合物以及它们作为多巴胺D3受体的部分激动剂或拮抗剂在治疗神经心理障碍方面的治疗应用。
• 3, 4-DIHYDRO-2-NAPHTHAMIDE DERIVATIVES AS SELECTIVE DOPAMINE D3 LIGANDS
  申请人：Sokoloff Pierre

  公开号：US20090124630A1

  公开（公告）日：2009-05-14

  The invention relates to 3,4-dihydro-2-naphthamide derivatives of formula (I), pharmaceutical compositions containing them and their therapeutic applications as partial agonists or antagonists of the dopamine D3 receptor for the treatment of neuropsychological disorders.

  本发明涉及式(I)的3,4-二氢-2-萘酰胺衍生物，含有它们的药物组合物以及它们作为多巴胺D3受体的部分激动剂或拮抗剂的治疗应用于神经心理障碍的治疗。
• Cyclization of Arylacetoacetates to Indene and Dihydronaphthalene Derivatives in Strong Acids. Evidence for Involvement of Further Protonation of O,O-Diprotonated β-Ketoester, Leading to Enhancement of Cyclization
  作者：Hiroaki Kurouchi、Hiromichi Sugimoto、Yuko Otani、Tomohiko Ohwada

  DOI：10.1021/ja908749u

  日期：2010.1.20

  The chemical features, such as substrate stability, product distribution, and substrate generality, and the reaction mechanism of Bronsted superacid-catalyzed cyclization reactions of aromatic ring-containing acetoacetates (beta-ketoesters) were examined in detail. While two types of carbonyl cyclization are possible, i.e., keto cyclization and ester cyclization, the former was found to take place exclusively. The reaction constitutes an efficient method to synthesize indene and 3,4-dihydronapthalene derivatives. Acid-base titration monitored with C-13 NMR spectroscopy showed that the acetoacetates are fully O-1,O-3-diprotonated at H-0 = -11. While the five-membered ring cyclization of the arylacetoacetates proceeded slowly at H-0 = -11, a linear increase in the rate of the cyclization was found with increasing acidity in the high acidity region of H-0 = -11.8 to -13.3. Therefore, the O-1,O-3-diprotonated acetoacetates exhibited some cyclizing reactivity, but they are not the reactive intermediates responsible for the acceleration of the cyclization in the high acidity region. The reactive cationic species might be formed by further protonation (or protosolvation) of the O-1,O-3-diprotonated acetoacetates; i.e., they may be tricationic species. Thermochemical data on the acid-catalyzed cyclization of the arylacetoacetates showed that the activation energy is decreased significantly as compared with that of the related acid-catalyzed cyclization reaction of a compound bearing a single functional group, such as a ketone. These findings indicate that intervention of the trication contributes to the activation of the cyclization of arylacetoacetates in strong acid, and the electron-withdrawing nature of the O-protonated ester functionality significantly increases the electrophilicity of the ketone moiety.
• Synthesis of 3, 6-Dimethyl-2, 3-dihydro-1<i>H</i>-cyclopent[<i>a</i>]anthracene. A Possible Dehydrogenation Product of Anthranoid Rearrangement Product of Steroids
  作者：Masao Nakazaki、Sachihiko Isoe

  DOI：10.1246/bcsj.32.1202

  日期：1959.11

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