2-carbocy-7-methylnaphthalene | 5159-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-carbocy-7-methylnaphthalene
• 英文别名: 7-methyl-2-naphthoic acid；7-methyl-2-naphthalenecarboxylic acid；7-Methyl-2-naphthoesaeure；7-methylnaphthalene-2-carboxylic acid
• CAS: 5159-64-8
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: WBCZIZCMFWRDIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  207-209 °C
• 沸点：
  347.9±11.0 °C(Predicted)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  2-carbocy-7-methylnaphthalene 在 溴 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 (8-Bromo-7-methylnaphthalen-2-yl)methanol
  参考文献：
  名称：

  Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00069a006
• 作为产物：
  描述：

  3,4-Dihydro-7-methyl-2-naphthalincarbonsaeureethylester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 2-carbocy-7-methylnaphthalene
  参考文献：
  名称：

  替代效应。14. 6-和 7-取代的 1-(2-NaphthyI)ethyl Chlorides 的溶剂分解

  摘要：

  合成了 9 种标题化合物，并在 45 °C 下在 80%(v/v) 丙酮水溶液中测定了它们的溶剂分解率。通过 LSFE 方程 (logk⁄k0=ρiσi+ρπ+σπ+)，在电感 (I) 和 π 电子 (Pi) 效应方面，证明了对每个取代基位置的 pi 供体取代基的影响)，就像 1-萘基系统中的那些一样。当这些数据与我们在相同条件下苯基、4-联苯基、2-芴基和 1-萘基系统的所有取代基效应数据相结合时，很明显 ρi 值与杜瓦的简单场效应之间的总体对应关系功能 (1⁄r) 令人满意。另一方面，ρπ+ 值似乎对 SCF-π 电荷差异值给出了略微不同的响应（1- 和 2-萘基系统的单独相关性）；这可能归因于仅在 1-萘基溶剂分解组中对 Pi 效应的空间效应。此外，I 效应的位置恒定性 (ρi,6−X−2⁄ρi,7−X−2=...

  DOI：

  10.1246/bcsj.52.3033

文献信息

• [EN] AMIDE DERIVATIVES AS SELECTIVE SEROTONIN RE-UPTAKE INHIBITORS<br/>[FR] DERIVES D'AMIDE EN TANT QU'INHIBITEURS SELECTIFS DU RECAPTAGE DE LA SEROTONINE
  申请人：PFIZER LTD

  公开号：WO2004111003A1

  公开（公告）日：2004-12-23

  The present invention relates to compounds of formula (I), wherein R1 is selected from: (a) (C1-C6)alkyl, optionally substituted by 1-3 substituents, each independently selected from: (i) CF3, OH, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C1-C6)alkoxy and halo; (ii) Phenyl, optionally fused with phenyl or cyclohexyl, said phenyl or fused phenyl optionally substituted with 1-3 groups selected from (C1-C6)alkyl, (C1-C6)alkyl ester, OH and halo; and (b) (C3-C6)cycloalkyl, optionally fused with (C5-C7)cycloalkyl, said cycloalkyl or fused cycloalkyl optionally substituted by OH, (C1-C6)alkyl, (C1-C6)alkoxy and halo. R2 is Phenyl, optionally fused to (C4-C6)cycloalkyl, phenyl or pyridyl, said phenyl or fused phenyl moiety optionally substituted with 1-3 groups each independently selected from (C1-C6)alkyl, (C1-C6)alkoxy, halo and OH. n is 1 to 2 and pharmaceutically acceptable salts, solvates or polymorphs thereof; With the proviso that when n is 2 and R1 is 2-(3,4-dimethoxylphenyl)-1-ethyl, 3,3­diphemyl-1-propyl or 2,4-difluorophenyl, then R2 cannot be 4-trifluoromethoxyphenyl, 2,4,6-trimethoxyphenyl, 4-acetoxyphenyl or 2,4-difluorophenyl; which are a class of selective serotonin re-uptake inhibitors (SSRIs).

  本发明涉及式(I)的化合物，其中R1从以下选项中选择：(a) (C1-C6)烷基，可选地被1-3个取代基取代，每个取代基独立地从以下选项中选择：(i) CF3，OH，(C1-C6)烷基，(C3-C6)环烷基，(C1-C6)烷氧基和卤素；(ii) 苯基，可选地与苯基或环己基融合，所述苯基或融合苯基可选地被1-3个取代基取代，所述取代基独立地从(C1-C6)烷基，(C1-C6)烷基酯，OH和卤素中选择；和(b) (C3-C6)环烷基，可选地与(C5-C7)环烷基融合，所述环烷基或融合环烷基可选地被OH，(C1-C6)烷基，(C1-C6)烷氧基和卤素取代。R2为苯基，可选地融合到(C4-C6)环烷基，苯基或吡啶基，所述苯基或融合苯基基团可选地被1-3个取代基取代，每个取代基独立地从(C1-C6)烷基，(C1-C6)烷氧基，卤素和OH中选择。n为1至2，以及其药学上可接受的盐、溶剂化合物或多形体；但是当n为2且R1为2-(3,4-二甲氧基苯基)-1-乙基，3,3-二苯基-1-丙基或2,4-二氟苯基时，R2不能为4-三氟甲氧基苯基，2,4,6-三甲氧基苯基，4-乙酰氧基苯基或2,4-二氟苯基；这些是一类选择性5-羟色胺再摄取抑制剂（SSRIs）。
• The selective oxidation of substituted aromatic hydrocarbons and the observation of uncoupling via redox cycling during naphthalene oxidation by the CYP101B1 system
  作者：Emma A. Hall、Md Raihan Sarkar、Stephen G. Bell

  DOI：10.1039/c7cy00088j

  日期：——

  derivatives. Methyl substituted naphthalenes were better substrates than ethylnaphthalenes and naphthalene itself. The highest product formation activity for a singly substituted alkylnaphthalene was obtained with 2-methylnaphthalene. The oxidation of alkylnaphthalenes was regioselective for the benzylic methyl or methine C–H bonds. The products from 1- and 2-ethylnaphthalene oxidation were highly enantioselective

  细胞色素P450单加氧酶CYP101B1，来自Novosphingobium芳烃DSM12444有效且选择性地氧化了各种萘和联苯衍生物。甲基取代的萘是比乙基萘和萘本身更好的底物。用2-甲基萘获得单取代烷基萘的最高产物形成活性。烷基萘的氧化对苄基甲基或次甲基CH键具有区域选择性。来自1-和2-乙基萘氧化的产物是高度对映体选择性的，并且明显过量地产生了单个立体异构体。与1-和2-甲基萘相比，双取代的底物2,7-二甲基萘具有更高的产物形成活性。甲基取代的联苯也是比联苯更好的底物，并且具有与1-甲基萘相似的生物催化参数。CYP101B1催化的2-和3-甲基联苯的氧化对甲基CH键具有选择性。例外的是4-甲基联苯的周转量，它以4'-（4-甲基苯基）苯酚为主要产物（占70％），其余部分由4-联苯甲醇构成。药物分子双氯芬酸也被CYP101B1区域选择性氧化为4'-羟基双氯芬酸。带有萘的CYP101B1系统
• Modulation on C- and N-Terminal Moieties of a Series of Potent and Selective Linear Tachykinin NK₂Receptor Antagonists
  作者：Martina Gensini、Maria Altamura、Tula Dimoulas、Valentina Fedi、Danilo Giannotti、Sandro Giuliani、Antonio Guidi、Nicholas J. S. Harmat、Stefania Meini、Rossano Nannicini、Franco Pasqui、Manuela Tramontana、Antonio Triolo、Carlo Alberto Maggi

  DOI：10.1002/cmdc.200900389

  日期：2010.1.4

  Herein we describe the synthesis of a series of new potent tachykinin NK2 receptor antagonists by the modulation of the C‐ and N‐terminal moieties of ibodutant (MEN 15596, 1). The N‐terminal benzo[b]thiophene ring was replaced by different substituted naphthalenes and benzofurans, while further modifications were evaluated at the C‐terminal tetrahydropyran moiety. Most compounds demonstrated a high affinity

  本文中，我们描述了一系列新的有效速激肽NK的合成2通过ibodutant的C-和N-末端部分的调制（MEN 15596，受体拮抗剂1）。N末端的苯并[ b ]噻吩环被不同的取代萘和苯并呋喃取代，同时在C末端的四氢吡喃部分评估了进一步的修饰。大多数化合物表现出对人NK 2受体的高亲和力和体外拮抗剂的高效力，表明可以在分子的两个末端引入广泛的取代基，而不会影响与NK 2受体的相互作用。对选定的化合物进行了体内测试，证实了其作为NK的活性2个拮抗剂。特别是，对豚鼠静脉内和静脉内给药后，化合物61b能够拮抗NK 2诱导的结肠收缩，其作用力和作用持续时间与参考化合物1（MEN 15596，ibodutant）完全相同。
• Structural assignment of 2,6- and 2,7-disubstituted naphthalenes and prediction of 13C nuclear magnetic resonance chemical shifts: applications of topology and two-dimensional NMR spectroscopy
  作者：Padmakar V Khadikar、Sadanand V Pathre、Anjali Shrivastava

  DOI：10.1016/s0960-894x(02)00556-5

  日期：2002.10

  putida, a bacterial strain, were made using two-dimensional nuclear Overhauser enhancement correlation spectroscopy (NOESEY). The two-dimensional long-range heteronuclear correlation NMR technique was also utilized for the assignment of quaternary carbons in the naphthalene system. In addition, we describe methods for prediction of 13C NMR chemical shifts of 2,6- and 2,7-disubstituted naphthalenes using

  使用二维核Overhauser增强相关光谱法（NOESEY）进行了恶臭假单胞菌（Pseudomonas putida）分离为二甲基萘氧化产物的单羧甲基萘的明确分配。二维远程异核相关核磁共振技术也用于萘体系中季碳的分配。此外，我们描述了使用拓扑方法预测2，6-和2,7-二取代萘的13C NMR化学位移的方法。该方法包括根据分子的拓扑表示来计算分子描述符，即维纳（W）和塞格德（Sz）指数。
• Amide derivatives as selective serotonin re-uptake inhibitors
  申请人：Andrews David Mark

  公开号：US20050014789A1

  公开（公告）日：2005-01-20

  The present invention relates to compounds of formula (I), wherein R 1 is selected from: (a) (C 1 -C 6 )alkyl, optionally substituted by 1-3 substituents, each independently selected from: (i) CF 3 , OH, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 6 )alkoxy and halo. (ii) Phenyl, optionally fused with phenyl or cyclohexyl, said phenyl or fused phenyl optionally substituted with 1-3 groups selected from (C 1 -C 6 )alkyl, (C 1 -C 6 )alkyl ester, OH and halo; and (b) (C 3 -C 6 )cycloalkyl, optionally fused with (C 5 -C 7 )cycloalkyl, said cycloalkyl or fused cycloalkyl optionally substituted by OH, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy and halo. R 2 is Phenyl, optionally fused to (C 4 -C 6 )cycloalkyl, phenyl or pyridyl, said phenyl or fused phenyl moiety optionally substituted with 1-3 groups each independently selected from (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo and OH; n is 1 to 2; and pharmaceutically acceptable salts, solvates or polymorphs thereof; With the proviso that when n is 2 and R 1 is 2-(3,4-dimethoxylphenyl)-1-ethyl, 3,3-diphenyl-1-propyl or 2,4-difluorophenyl, then R 2 cannot be 4-trifluoromethoxyphenyl, 2,4,6-trimethoxyphenyl, 4-acetoxyphenyl or 2,4-difluorophenyl; which are a class of selective serotonin re-uptake inhibitors (SSRIs).

  本发明涉及式（I）的化合物，其中R1选自：（a）（C1-C6）烷基，可选地被1-3个取代基取代，每个取代基独立地选自：（i）CF3，OH，（C1-C6）烷基，（C3-C6）环烷基，（C1-C6）烷氧基和卤素；（ii）苯基，可选地与苯基或环己基融合，所述苯基或融合苯基可选地被1-3个选自（C1-C6）烷基，（C1-C6）烷酯，OH和卤素的基团取代；和（b）（C3-C6）环烷基，可选地与（C5-C7）环烷基融合，所述环烷基或融合环烷基可选地被OH，（C1-C6）烷基，（C1-C6）烷氧基和卤素取代。R2为苯基，可选地融合到（C4-C6）环烷基、苯基或吡啶基上，所述苯基或融合苯基基团可选地被1-3个独立选自（C1-C6）烷基，（C1-C6）烷氧基，卤素和OH的基团取代；n为1到2；以及其药学上可接受的盐、溶剂或多型性；但当n为2且R1为2-(3,4-二甲氧基苯基)-1-乙基、3,3-二苯基-1-丙基或2,4-二氟苯基时，则R2不能是4-三氟甲氧基苯基、2,4,6-三甲氧基苯基、4-乙酰氧基苯基或2,4-二氟苯基；这是一类选择性5-羟色胺再摄取抑制剂（SSRI）。