4-bromo-2-isopropylanisole | 24591-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-2-isopropylanisole
• 英文别名: 4-Brom-2-isopropyl-anisol；4-bromo-2-isopropyl-1-methoxybenzene；3-isopropyl-4-methoxybromobenzene；4-bromo-1-methoxy-2-propan-2-ylbenzene
• CAS: 24591-33-1
• 化学式: C₁₀H₁₃BrO
• 分子量: 229.117
• InChiKey: CFNMTRKNNCKHBM-UHFFFAOYSA-N

物化性质

• 沸点：
  86-87 °C(Press: 2 Torr)
• 密度：
  1.2462 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4-bromo-2-isopropylanisole 在 palladium on activated charcoal sodium hydroxide 、 正丁基锂 、 氢气 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 生成 [4-(3-isopropyl-4-methoxy-benzyl)-3,5-dimethyl-phenoxy]-acetic acid
  参考文献：
  名称：

  A Functionally Orthogonal Ligand−Receptor Pair Created by Targeting the Allosteric Mechanism of the Thyroid Hormone Receptor

  摘要：

  Nuclear receptors are ligand-dependent transcription factors that are of interest as potential tools to artificially regulate gene expression. Ligand binding induces a conformational change involving helix-12 which forms part of the dimerization interface used to bind transcriptional coactivators. When triiodothyronine (T3) binds the thyroid hormone receptor (TR) it indirectly contacts helix-12 through intermediary residues His(435) and Phe(451) termed a His-Phe switch. The mutant TR beta(H435A) is nonresponsive to physiological concentrations of T3 but can be activated by the synthetic hormone analogue QH2 which potently activates His435 -> Ala mutant at concentrations that do not activate the wild-type receptors TR alpha and TR beta. QH2 does not show antagonist behavior with the wild-type TRs. QH2's functionally orthogonal behavior with TR beta(H435A) is preserved on the three consensus thyroid hormone response elements.

  DOI：

  10.1021/ja060760v
• 作为产物：
  描述：

  3-(1-hydroxy-1-methylethyl)-4-methoxyphenylethanol 在 palladium on activated charcoal 18-冠醚-6 、 4 A molecular sieve 、 Celite 、 氢气 、 溶剂黄146 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 potassium bromide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 4-bromo-2-isopropylanisole
  参考文献：
  名称：

  芳香族二萜的合成 12-Hydroxy-abieta-8,11,13-trien-3,7-dione 的合成

  摘要：

  摘要 涉及合适二烯的阳离子环化的模型研究提供了标题化合物的合成。描述了从可用的芳族原料制备二烯和环化产物的改性。

  DOI：

  10.1080/00397919108020799

文献信息

• Syntheses and evaluation of multicaulin and miltirone-like compounds as antituberculosis agents
  作者：Serdar Burmaoğlu、Hatice Seçinti、Erkan Mozioğlu、Ahmet C. Gören、Ramazan Altundaş、Hasan Seçen

  DOI：10.1080/14756366.2017.1337758

  日期：2017.1.1

  Pschorr coupling of 4-(3-isopropyl-4-methoxyphenyl)-2-(2-aminophenyl)ethane (13) to give 2-isopropyl-3-methoxy-9,10-dihydrophenanthrene (9) and 4-isopropyl-3-methoxy-9,10-dihydrophenanthrene (9a). Compound 9 was converted to multicaulin and miltirone-like phenanthrene derivatives by further reactions. The best antituberculosis activity was exhibited by 2-isopropylphenanthrene-3-ol (11).

  合成了四种多花青素和类似miltirone的菲衍生物，并作为抗结核药进行了评估。合成的关键步骤是4-（3-异丙基-4-甲氧基苯基）-2-（2-氨基苯基）乙烷（13）的Pschorr偶联，得到2-异丙基-3-甲氧基-9,10-二氢菲（9 ）和4-异丙基-3-甲氧基-9,10-二氢菲（9a）。通过进一步的反应，将化合物9转化为多花青素和米替农样的菲衍生物。2-异丙基菲-3-醇（11）表现出最佳的抗结核活性。
• NOVEL 6-5 BICYCIC HETEROCYCLIC DERIVATIVE AND MEDICAL USE THEREOF
  申请人：Sanwa Kagaku Kenkyusho Co., Ltd

  公开号：EP2036887A1

  公开（公告）日：2009-03-18

  An object of the present invention is to provide a medicament as a thyroid hormone receptor ligand which is sufficient in drug efficacy and safety, and has the excellent action as a drug. The present invention provides a compound represented by the following general formula (I) or a pharmaceutically acceptable salt thereof: [wherein [Chemical Formula 2] is a single bond or a double bond; A is -CH2- or -CO-; X, Y, and Z are each independently a nitrogen atom or a carbon atom; R1 is a hydrogen atom or an aralkyl group; R2 is an alkyl group or an aralkyl group, etc.; R3 is a hydrogen atom or an alkyl group, etc.; R4 is a hydrogen atom or an alkyl group; R5 is a hydrogen atom, an alkyl group or a halo lower alkyl group, etc.; R6 is a hydrogen atom or an alkyl group; R7 is a hydrogen atom, etc.; R8 is a hydrogen atom, or an alkyl group, etc.; and E is -NHCO-G-COR12, etc. (wherein G is a single bond or an alkylene group, and R12 is a hydroxy group or an alkoxy group)].

  本发明的目的是提供一种药物，作为甲状腺激素受体配体，其在药物疗效和安全性上足够，并且具有作为药物的优秀作用。本发明提供了一种由以下通式（I）表示的化合物或其药用可接受的盐：[其中[化学公式2]是单键或双键；A是-CH2-或-CO-；X、Y和Z各自独立为氮原子或碳原子；R1是氢原子或芳烷基团；R2是烷基团或芳烷基团等；R3是氢原子或烷基团等；R4是氢原子或烷基团；R5是氢原子、烷基团或卤素低烷基团等；R6是氢原子或烷基团；R7是氢原子等；R8是氢原子或烷基团等；E是-NHCO-G-COR12等（其中G是单键或亚烷基团，R12是羟基或烷氧基）]。
• Total synthesis of (±)-Scrodentoid A
  作者：Shao-Dong Lv、Tian Tian、Liu-Qiang Zhang、Si-Yu Xu、Dong-Hai Zhao、Jun-Jie Wang、Jian-Guo Fu、Yi-Ming Li、Chen-Guo Feng

  DOI：10.1016/j.tet.2019.130774

  日期：2019.12

  An efficient total synthesis of scrodentoid A was accomplished starting from a Hagemann's ester and a substituted (2-bromoethyl)benzene. Key reactions in this synthesis include C-alkylation of the Hagemann's ester, 6-endo-Trig cationic cyclization of an enone and Lewis acid promoted isomerization of a cis-fused ketone.

  从哈格曼酸酯和取代的（2-溴乙基）苯开始，完成了高效的scrodentoid A的全合成。该合成中的关键反应包括哈格曼酯的C-烷基化，烯酮的6-内-Trig阳离子环化和路易斯酸促进的顺式融合酮的异构化。
• Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes
  作者：Zhonglin Tao、Kevin A. Robb、Kuo Zhao、Scott E. Denmark

  DOI：10.1021/jacs.8b01660

  日期：2018.3.14

  Homogeranylarenes and ortho-geranylphenols undergo polycyclization in good yield, diastereoselectivity, and enantioselectivity. The stereodetermining step is the generation of an enantiomerically enriched thiiranium ion from a terminal alkene and a sulfenylating agent in the presence of a chiral Lewis basic catalyst. The use of hexafluoroisopropyl alcohol as the solvent is crucial to obtain good yields

  描述了硫鎓离子引发的催化对映选择性多烯环化。同香叶基芳烃和邻香叶基酚以良好的收率、非对映选择性和对映选择性进行多环化。立体决定步骤是在手性路易斯碱性催化剂存在下，由末端烯烃和磺化剂生成对映体富集的噻喃离子。使用六氟异丙醇作为溶剂对于获得良好的产率至关重要。反应产生的硫醚部分随后可以在环化后转化为不同的氧和碳官能团。 (+)-ferruginol 和 (+)-hinokiol 的对映选择性合成证明了该方法的实用性。
• Desymmetric Enantioselective Reduction of Cyclic 1,3-Diketones Catalyzed by a Recyclable <i>P</i>-Chiral Phosphinamide Organocatalyst
  作者：Xu-Long Qin、Ang Li、Fu-She Han

  DOI：10.1021/jacs.1c00277

  日期：2021.2.24

  The P-stereogenic phosphinamides are a structurally novel skeletal class which has not been investigated as chiral organocatalysts. However, chiral cyclic 3-hydroxy ketones are widely used as building blocks in the synthesis of natural products and bioactive compounds. However, general and practical methods for the synthesis of such chiral compounds remain underdeveloped. Herein, we demonstrate that

  的P -stereogenic phosphinamides是还没有被研究作为手性有机催化剂结构上新颖的骨架类。然而，手性环状3-羟基酮被广泛用作天然产物和生物活性化合物合成中的结构单元。但是，合成这类手性化合物的一般和实用方法仍未开发。在此，我们证明了P-立体生成的次膦酰胺是用于环状1，3-二酮的不对称对映选择性还原的有力有机催化剂，为合成手性环状3-羟基酮提供了有用的方法。该协议显示了广泛的底物范围，适用于一系列环状的2,2-二取代的五元和六元1,3-二酮。可以获得具有高对映选择性（高达98％ee）和非对映选择性（高达99：1 dr）的带有全碳手性季中心的手性环状3-羟基酮产物。最重要的是，反应实际上可以以克为单位进行，并且催化剂可以重复使用而不会损害催化效率。机理研究表明，由P形成的中间体-立体生成的次膦酰胺和儿茶酚硼烷是真正的催化活性物质。结果本文公开用于设计和使用显影等反应兆头P