2-(benzyloxy)-1,6-dibromonaphthalene | 127399-79-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(benzyloxy)-1,6-dibromonaphthalene
• 英文别名: 1,6-Dibromo-2-phenylmethoxynaphthalene
• CAS: 127399-79-5
• 化学式: C₁₇H₁₂Br₂O
• 分子量: 392.09
• InChiKey: ZNUSDAXAMILEPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(benzyloxy)-1,6-dibromonaphthalene 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 150.0 ℃ 、150.0 kPa 条件下， 反应 4.25h， 生成 4-(2-(benzyloxy)-6-(3-(benzyloxy)phenyl)naphthalen-1-yl)-1H-indole
  参考文献：
  名称：

  Lead Optimization of 17β-HSD1 Inhibitors of the (Hydroxyphenyl)naphthol Sulfonamide Type for the Treatment of Endometriosis

  摘要：

  The reduction of estrone to estradiol, the most potent estrogen in human, is catalyzed by 17 beta-hydroxysteroid dehydrogenase type 1 (17 beta-HSD1). A promising approach for the treatment of estrogen-dependent diseases is the reduction of intracellular estradiol formation by inhibition of 17 beta-HSD1. For the species-specific optimization of the (hydroxyphenyl)naphthols, a combinatorial approach was applied and enhanced by a focused synthesis that resulted in the aromatic-substituted (hydroxyphenyl)naphthol sulfonamides. Rigidification of 12 led to the 4-indolylsulfonamide 30, which is a highly active and selective human 17 beta-HSD1 inhibitor, as well as a highly potent and selective inhibitor of 17 beta-HSD1 from Callithrix jacchus. It shows no affinity to the estrogen receptors a and 9 and good intracellular activity (T47D). Thus, compound 30 shows good properties for further ADMET studies and might be a candidate for the in vivo proof of concept in C. jacchus.

  DOI：

  10.1021/jm201735j
• 作为产物：
  描述：

  6-bromo-1-diazonaphthalen-2(1H)-one 、 溴甲苯 在 rhodium(II) pivalate 作用下， 以 氟苯 为溶剂， 反应 15.0h， 以72%的产率得到2-(benzyloxy)-1,6-dibromonaphthalene
  参考文献：
  名称：

  Rh（II）催化重氮化合物合成多种官能化卤代萘醚和酯的策略及其在聚芳族化合物中的应用

  摘要：

  摘要 通过铑（II）催化的易得的重氮化合物与苄基卤化物或酰卤的反应，可以高效且简单地合成各种官能化的卤代萘基醚和酯，且收率适中。该方法具有许多优点，例如易于处理，温和的反应条件，无溴或无氯路线以及使用有效的催化剂。使用Suzuki反应将合成的化合物进一步转化为有价值的多芳族化合物。 通过铑（II）催化的易得的重氮化合物与苄基卤化物或酰卤的反应，可以高效且简单地合成各种官能化的卤代萘基醚和酯，且收率适中。该方法具有许多优点，例如易于处理，温和的反应条件，无溴或无氯路线以及使用有效的催化剂。使用Suzuki反应将合成的化合物进一步转化为有价值的多芳族化合物。

  DOI：

  10.1055/s-0035-1561295

文献信息

• Monomethyl ether derivatives of 7,8-dihydroxy- and 8,9-dihydroxy-4-propyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolines as possible products of metabolism by catechol-O-methyltransferase
  作者：Joseph G. Cannon、Kathleen A. Walker、Antonio Montanari、John Paul Long、Jan R. Flynn

  DOI：10.1021/jm00169a031

  日期：1990.7

  possible metabolites arising from in vitro action of catechol-O-methyltransferase upon 7,8-dihydroxy- and 8,9-dihydroxy-4-n-propyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolines (11, 12), all four possible monomethyl ether derivatives have been synthesized. Incubation of 11 and 12 with the enzyme revealed that the 8,9-dihydroxy positional isomer 12 (which contains the dopamine moiety held in the beta

  为了促进鉴定由邻苯二酚-O-甲基转移酶对7,8-二羟基-和8,9-二羟基-4-正丙基-1,2,3,4,4a，5的体外作用产生的可能的代谢物，6，10b-八氢苯并[f]喹啉（11、12），已经合成了所有四种可能的单甲醚衍生物。用该酶孵育11和12后发现8,9-二羟基位置异构体12（包含保持在β构象中的多巴胺部分）但不包含7,8-二羟基异构体11（保持在alpha中的多巴胺部分）构象）是酶的底物。唯一可检测的产物12是8-羟基-9-甲氧基衍生物15，其中多巴胺部分的“间位”羟基被醚化。
• Highly Conjugated Molecules from Dibromonaphthyl Derivatives and 4-Vinylpyridine or 4-Acetoxystyrene by the Heck Reaction
  作者：C. C. Chang、K. J. Chen、L. J. Yu

  DOI：10.1021/jo990697a

  日期：1999.7.1

  Palladium-catalyzed coupling of 1,6- and 2,6-dibromonaphthyl derivatives with 4-vinylpyridine or 4-acetoxystyrene resulted in mono- and bis-arylvinylation depending on the choice of reaction conditions. For the 1,6-dibromoarenes, the mono-arylvinylated derivative at position-6 was the sole product in the presence of (o-tol)(3)P/Et3N. The bis-arylvinylated derivative was the major product, accompanied by a minor product, arylvinylated at position-6 and reduced at position-1, in the presence of (o-tol)(3)P/Et3N/MeCN. For the 2,6-dibromoarenes, the bis-arylvinylated derivative was the sole product in the presence of either Ph3P or (o-tol)(3)P, if provided with a small volume of Et3N/MeCN solvent, and the mono-arylvinylated derivative was the major product with larger solvent volume and higher haloarene ratio. Fluorescence intensities of 2,6-bis-arylvinylated products were 2 to 3 orders of magnitude higher than that of stilbene. Nematic phases, at relatively high temperatures, were observed for some of the rodlike molecules. Shown by H-1 NMR study, at the photostationary state of isomerization, smaller fractions of cis-form were obtained for molecules that exhibited larger fluorescence quantum yields. The results presented here are beneficial to the pursuit of nonlinear optical materials, fluorescent mesogens, photo- and electroactive materials.
• CANNON, JOSEPH G.;WALKER, KATHLEEN A.;MONTANARI, ANTONIO;LONG, JOHN PAUL;+, J. MED. CHEM., 33,(1990) N, C. 2000-2006
  作者：CANNON, JOSEPH G.、WALKER, KATHLEEN A.、MONTANARI, ANTONIO、LONG, JOHN PAUL、+

  DOI：——

  日期：——