5,6-dihydro-naphthalene-2-carboxylic acid | 151623-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,6-dihydro-naphthalene-2-carboxylic acid
• 英文别名: 5,6-Dihydronaphthalene-2-carboxylic acid
• CAS: 151623-58-4
• 化学式: C₁₁H₁₀O₂
• mdl: MFCD20645143
• 分子量: 174.199
• InChiKey: ZIOKEAPOECTGSN-UHFFFAOYSA-N

物化性质

• 沸点：
  329.7±31.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 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：

  5,6-dihydro-naphthalene-2-carboxylic acid 在 N-溴代丁二酰亚胺(NBS) 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 sodium methylate 、 N-溴代乙酰胺 作用下， 以 四氢呋喃 、 四氯化碳 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 7,8-Epoxide-7,8-dihydronaphthalene-2-carboxylic acid
  参考文献：
  名称：

  Hapten design and development of an ELISA (enzyme-linked immunosorbent assay) for the detection of the mercapturic acid conjugates of naphthalene

  摘要：

  Measurement of urinary metabolites constitutes a noninvasive method to assess toxic exposure. Naphthalene is a common environmental contaminant showing selective pulmonary toxicity in mice and presumably is involved in development of lung disease in man (Buckpitt, A.R.; Franklin, R.B. Pharmacol. Ther. 1989, 41, 339). A glutathione-based detoxification pathway leads to the formation of the mercapturic acid conjugates [NaphMA 1, (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-1-hydroxy-2-naphthyl]cysteine] and (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-2-hydroxy-1-naphthyl]cysteine] which are excreted in urine. Herein we report the development of an immunoassay for the specific detection of these urinary metabolites. This study confirms the importance of appropriate hapten design and synthesis in controlling the specificity and sensitivity of the immunoassay. Our strategy was to prepare haptens that allow covalent attachment to a carrier protein at a site opposite to the N-acetylcysteine moiety. The antibodies obtained by immunizing six rabbits with these NaphMA derivatives (haptens 13 and 14) have been used for the development of an ELISA (enzyme-linked immunosorbent assay) which detects NaphMA 1 in the range between 100 and 6 pg/mL with an I50 of 29 pg/mL. Its ability to detect these important naphthalene metabolites in human urine is demonstrated.

  DOI：

  10.1021/jo00078a039
• 作为产物：
  描述：

  5,6-dihydro-naphthalene-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到5,6-dihydro-naphthalene-2-carboxylic acid
  参考文献：
  名称：

  Hapten design and development of an ELISA (enzyme-linked immunosorbent assay) for the detection of the mercapturic acid conjugates of naphthalene

  摘要：

  Measurement of urinary metabolites constitutes a noninvasive method to assess toxic exposure. Naphthalene is a common environmental contaminant showing selective pulmonary toxicity in mice and presumably is involved in development of lung disease in man (Buckpitt, A.R.; Franklin, R.B. Pharmacol. Ther. 1989, 41, 339). A glutathione-based detoxification pathway leads to the formation of the mercapturic acid conjugates [NaphMA 1, (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-1-hydroxy-2-naphthyl]cysteine] and (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-2-hydroxy-1-naphthyl]cysteine] which are excreted in urine. Herein we report the development of an immunoassay for the specific detection of these urinary metabolites. This study confirms the importance of appropriate hapten design and synthesis in controlling the specificity and sensitivity of the immunoassay. Our strategy was to prepare haptens that allow covalent attachment to a carrier protein at a site opposite to the N-acetylcysteine moiety. The antibodies obtained by immunizing six rabbits with these NaphMA derivatives (haptens 13 and 14) have been used for the development of an ELISA (enzyme-linked immunosorbent assay) which detects NaphMA 1 in the range between 100 and 6 pg/mL with an I50 of 29 pg/mL. Its ability to detect these important naphthalene metabolites in human urine is demonstrated.

  DOI：

  10.1021/jo00078a039

文献信息

• Synthesis of aromatic aldehydes by organocatalytic [4+2] and [3+3] cycloaddition of α,β-unsaturated aldehydes
  作者：Bor-Cherng Hong、Hsing-Chang Tseng、Shang-Hung Chen

  DOI：10.1016/j.tet.2007.01.039

  日期：2007.3

  Organocatalytic inter- and intramolecular [4+2] and [3+3] cycloadditions of α,β-unsaturated aldehydes to give polysubstituted aromatic aldehydes are described. High periselectivity for the cycloadditions, with catalyst effects exerted by l-proline and pyrrolidine–HOAc, as well as cocatalyst, additive effects, has been observed.

  描述了α，β-不饱和醛的有机催化的分子间和分子内[4 + 2]和[3 + 3]环加成以得到多取代的芳族醛。观察到对环加成反应的高选择性是由l-脯氨酸和吡咯烷-HOAc产生的催化剂作用，以及助催化剂的加成作用。
• Catalytic Asymmetric Intermolecular Bromoesterification of Unfunctionalized Olefins
  作者：Lijun Li、Cunxiang Su、Xiaoqin Liu、Hua Tian、Yian Shi

  DOI：10.1021/ol501542r

  日期：2014.7.18

  An asymmetric intermolecular bromoesterification of unfunctionalized olefins catalyzed by (DHQD)2PHAL is described. Optically active bromoesters can be obtained with up to 92% ee.

  描述了通过（DHQD）2 PHAL催化的未官能化烯烃的不对称分子间溴代酯化反应。可以以高达92％ee获得旋光性溴酸酯。
• [EN] BENZOPYRAN AND BENZOTHIOPYRAN DERIVATIVES HAVING RETINOID ANTAGONIST-LIKE ACTIVITY<br/>[FR] DERIVES DE BENZOPYRANE ET BENZOTHYOPYRANE PRESENTANT UNE ACTIVITE RETINOÏDE DE TYPE ANTAGONISTE
  申请人：ALLERGAN SALES, INC.

  公开号：WO1999033821A1

  公开（公告）日：1999-07-08

  (EN) 2,2-Dialkyl- 4-aryl-substituted benzopyran and benzothiopyran derivatives of formula (I) where the symbols have the meaning described in the specification, have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action or RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists.(FR) L'invention concerne des dérivés de 2,2-dialkyl-benzopyrane et benzothiopyrane à substitution 4-aryl de formule (I), dont les symboles sont définis dans le descriptif. Ces dérivés présentent des activités biologiques rétinoïdes de type antagonistes et/ou hormones négatives. Les antagonistes de RAR de l'invention peuvent être administrés aux mammifères, y compris aux humains, pour prévenir ou réduire l'action d'antagonistes de RAR sur les sites récepteurs liés. En particulier, les agonistes de RAR sont administrés ou co-administrés avec des médicaments rétinoïdes pour empêcher ou atténuer la toxicité ou les effets secondaires des rétinoïdes, de la vitamine A ou des précurseurs de la vitamine A. Les hormones négatives rétinoïdes peuvent être utilisées pour renforcer les activités d'autres rétinoïdes et celles d'agonistes de récepteurs nucléaires.

  2,2-二烷基-4-芳基取代苯并吡喃和苯并噻吩的衍生物，其化学式为(I)，其中符号的含义在说明书中描述，具有视黄醇负性激素和/或拮抗剂样生物活性。发明的RAR拮抗剂可用于哺乳动物，包括人类，以防止或减少RAR激动剂对结合受体位点的作用。具体而言，RAR激动剂与视黄醇药物一起给予或联合给予，以防止或缓解视黄醇或维生素A或维生素A前体引起的毒性或副作用。视黄醇负性激素可用于增强其他视黄醇和核受体激动剂的活性。
• Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities
  申请人：——

  公开号：US20030219832A1

  公开（公告）日：2003-11-27

  Aryl-substituted and aryl and (3-oxo-1-propenly)-substituted benzopyran, benzothiopyran, 1,2-dihydroquinoline, and 5,6-dihydronaphthalene derivatives have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists. For example, the retinoid negative hormone called AGN 193109 effectively increased the effectiveness of other retinoids and steroid hormones in in vitro transactivation assays. Additionally, transactivation assays can be used to identify compounds having negative hormone activity. These assays are based on the ability of negative hormones to down-regulate the activity of chimeric retinoid receptors engineered to possess a constitutive transcription activator domain.

  取代芳基和取代芳基和（3-氧代-1-丙烯基）基苯并吡喃、苯并硫吡喃、1,2-二氢喹啉和5,6-二氢萘衍生物具有视黄醛受体负性激素和/或拮抗剂样的生物活性。发明的RAR拮抗剂可用于哺乳动物，包括人类，以防止或减少RAR激动剂对结合受体位点的作用。具体而言，RAR激动剂与视黄醇药物一起使用或联合使用，以防止或缓解视黄醇或维生素A或维生素A前体引起的毒性或副作用。视黄醛负性激素可用于增强其他视黄醇和核受体激动剂的活性。例如，名为AGN 193109的视黄醛负性激素在体外转录激活测定中有效地增加了其他视黄醇和类固醇激素的效力。此外，转录激活测定可用于鉴定具有负性激素活性的化合物。这些测定基于负性激素降调节嵌合视黄醛受体活性的能力。
• SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-SS-D-ARABINOFURANOSYL)CYTOSINE
  申请人：Fujifilm Corporation

  公开号：EP3184112A1

  公开（公告）日：2017-06-28

  Synthetic intermediate of 1-(2-deoxy-2-fluoro-4-thio-β-D-arabinofuranosyl)cytosine A compound represented by the formula [1F]: wherein R1 represents a hydrogen atom or a hydroxyl protecting group; R2 represents a hydrogen atom or a hydroxyl-protecting group; R3C represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group or -OR3a corresponding to a hydroxyl-protecting group; R3D represents a hydrogen atom, a halogen atom, an optionally substituted alkyl group or -OR3a corresponding to a hydroxyl-protecting group; R4 represents a halogen atom, a hydroxyl group, an optionally substituted alkylsulfonyloxy group or an optionally substituted arylsulfonyloxy group; R5 and R6 together represent =O or =NOR7 wherein R7 represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted heterocyclic group or an optionally substituted silyl group; or R4 and R5 together represent a sulfur atom; and R6 represents a hydroxyl group. The compound is useful as an intermediate for producing a thionucleoside.

  1-(2-脱氧-2-氟-4-硫代-β-D-阿拉伯呋喃糖基)胞嘧啶的合成中间体 由式[1F]表示的化合物： 其中 R1 代表氢原子或羟基保护基团； R2 代表氢原子或羟基保护基团； R3C 代表氢原子、卤素原子、任选取代的烷基或与羟基保护基团相对应的-OR3a； R3D 代表氢原子、卤素原子、任选取代的烷基或与羟基保护基团相对应的-OR3a；R4 代表卤原子、羟基、任选取代的烷基磺酰氧基或任选取代的芳基磺酰氧基；R5 和 R6 共同代表 =O 或 =NOR7 其中 R7 代表氢原子、任选取代的烷基、任选取代的芳基、任选取代的杂环基或任选取代的硅基；或 R4 和 R5 共同代表硫原子；R6 代表羟基。该化合物可用作生产硫代核苷的中间体。