7-bromo-4-methyl-1,2,3,4-tetrahydro-1H-naphthalen-1-one | 51644-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 7-bromo-4-methyl-1,2,3,4-tetrahydro-1H-naphthalen-1-one
• 英文别名: 7-bromo-1-oxo-4-methyl-1,2,3,4-tetrahydronaphthalene；7-Brom-4-methyl-1,2,3,4-tetrahydro-naphthalin-1-on；7-Bromo-4-methyl-1,2,3,4-tetrahydronaphthalen-1-one；7-bromo-4-methyl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 51644-34-9
• 化学式: C₁₁H₁₁BrO
• 分子量: 239.112
• InChiKey: WPBQXWWFPSGWKI-UHFFFAOYSA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  135-137 °C(Press: 0.2 Torr)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-bromo-4-methyl-1,2,3,4-tetrahydro-1H-naphthalen-1-one 在 正丁基锂 、 Ti⁽³⁺⁾*NO₃^(1-) 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 69.08h， 生成 3-bromo-9-methyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-one
  参考文献：
  名称：

  Total Synthesis of the Phenalenone Diterpene Salvilenone

  摘要：

  The application of a photochemical aromatic annulation strategy in a highly efficient total synthesis of the phenalenone diterpene salvilenone is reported. The pivotal step in the synthesis involves the assembly of the key dihydrophenalene 29 in one step via an annulation involving the siloxyalkyne 28 and either diazo ketone 8 or 9. The synthesis of the alpha-benzosuberone 8 was achieved in three steps beginning with 2-methylcyclopentanone by a route featuring an ''aryne-enolate condensation'' reaction. The alternative aromatic annulation substrate, the beta-benzosuberone 9, was prepared in four steps by a route based on the regiocontrolled ring expansion of the alpha-methylenetetralin 27. The key aromatic annulation was then accomplished by irradiating a mixture of either diazo ketone 8 or 9 and 1.4 equiv of the siloxyalkyne 28 in 1,2-dichloroethane at 20-25 degrees C using a standard Rayonet photochemical reactor. The reaction mixture was next diluted with an equal volume of solvent and heated overnight at 80 degrees C to complete the annulation; concentration and chromatographic purification furnished the tricyclic phenol 29 as colorless crystals in 60-71% yield. Finally, annulation of the furan ring and oxidation required three steps and provided the phenalenone diterpene in good yield. The synthetic routes described herein provide access to salvilenone in only seven or eight steps (via the alpha- and beta-benzosuberone strategies, respectively), half the number of steps required using the classical linear substitution approach reported previously. These highly efficient syntheses demonstrate the ability of the photochemical aromatic annulation strategy to dramatically streamline the synthesis of polycyclic aromatic compounds.

  DOI：

  10.1021/ja00100a009
• 作为产物：
  描述：

  3-(4-Bromophenyl)butyl methanesulfonate 在 二环己烷并-18-冠醚-6 氢氧化钾 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 56.0h， 生成 7-bromo-4-methyl-1,2,3,4-tetrahydro-1H-naphthalen-1-one
  参考文献：
  名称：

  Synthesis of nuclear monobromobenz[a]anthracenes

  摘要：

  DOI：

  10.1021/jo00165a029

文献信息

• [EN] 1-ARYLSULPHONYL, ARYL(THIO)CARBONYL PYRIDAZINO DERIVATIVES AND METHODS OF PREPARATION<br/>[FR] DERIVES DE PYRIDAZINE D'ARYLSULPHONYL-1 ET D'ARYL(THIO)CARBONYLE ET LEURS PROCEDES DE PREPARATION
  申请人：ORTHO PHARMACEUTICAL CORPORATION

  公开号：WO1997017332A1

  公开（公告）日：1997-05-15

  (EN) 1-Arylsulphonyl, arylcarbonyl and aryl(thio)carbonyl pyridazino derivatives and processes for making said derivatives are described. The novel derivatives are non-steroidal heterocyclic compounds which act as selective progestins and/or antiprogestins having a high $i(in vitro) affinity for either the uterine, breast or bone progestin receptor. As such, the non-steroidal heterocyclic derivatives are useful in contraception, menopause, osteoporosis or endometriosis.(FR) L'invention porte sur des dérivés de pyridazine d'arylsulphonyl-1, d'arylcarbonyle et d'arylthiocarbonyle et sur leurs procédés de préparation. Ces dérivés de type nouveau sont des composés hétérocycliques non stéroïdiens agissant en tant que progestérones sélectives et/ou antiprogestérones ayant une affinité $i(in vitro) élevée par le récepteur des progestérones soit de l'utérus, soit du sein, soit des os. En tant que tels, ces dérivés hétérocycliques non stéroïdiens sont utiles dans le cadre de la contraception, de la ménopause, de l'ostéoporose ou de l'endométriose.

  以下是对英文文本的翻译，确保准确传达其科学内容和用途： **中文翻译：** 描述了1- Battlefield-sulphonyl、aryl-carbonyl 和 aryl-thio-carbonyl 的吡咯衍生物及其制备方法。这些新型衍生物是非甾体类杂环化合物，作用于子宫、乳腺或骨的促性腺激素受体，具有在 vitro 时的高亲靶性。因此，作为选择性促性腺激素类药物或反促性腺激素类药物的非甾体类杂环化合物，在避孕、减经、骨质疏松或功卵膜炎中有重要应用价值。
• Discovery of Potent and Selective Benzothiazole Hydrazone Inhibitors of Bcl-X_L
  作者：Brad E. Sleebs、Wilhemus J. A. Kersten、Sanji Kulasegaram、George Nikolakopoulos、Effie Hatzis、Rebecca M. Moss、John P. Parisot、Hong Yang、Peter E. Czabotar、W. Douglas Fairlie、Erinna F. Lee、Jerry M. Adams、Lin Chen、Mark F. van Delft、Kym N. Lowes、Andrew Wei、David C.S. Huang、Peter M. Colman、Ian P. Street、Jonathan B. Baell、Keith Watson、Guillaume Lessene

  DOI：10.1021/jm400556w

  日期：2013.7.11

  Developing potent molecules that inhibit Bcl-2 family mediated apoptosis affords opportunities to treat cancers via reactivation of the cell death machinery. We describe the hit-to-lead development of selective Bcl-X-L inhibitors originating from a high-throughput screening campaign. Small structural changes to the hit compound increased binding affinity more than 300-fold (to IC50 < 20 nM). This molecular series exhibits drug-like characteristics, low molecular weights (M-w < 450) and unprecedented selectivity for Bcl-X-L. Surface plasmon resonance experiments afford strong evidence of binding affinity within the hydrophobic groove of Bcl-X-L. Biological experiments using engineered Mcl-1 deficient mouse embryonic fibroblasts (MEFs, reliant only on Bcl-X-L, for survival) and Bax/Bak deficient MEFs (insensitive to selective activation of Bcl-2-driven apoptosis) support a mechanism-based induction of apoptosis. This manuscript describes the first series of selective small-molecule inhibitors of Bcl-X-L and provides promising leads for the development of efficacious therapeutics against solid tumors and chemoresistant cancer cell lines.
• NEWMAN, M. S.;PRABHU, V. S.;VEERARAGHAVAN, S., J. ORG. CHEM., 1983, 48, N 17, 2926-2928
  作者：NEWMAN, M. S.、PRABHU, V. S.、VEERARAGHAVAN, S.

  DOI：——

  日期：——
• US5753655A
  申请人：——

  公开号：US5753655A

  公开（公告）日：1998-05-19

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