5-bromo-1,3-diisopropyl-2-(methoxymethoxy)benzene | 168196-99-4

• 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: 5-bromo-1,3-diisopropyl-2-(methoxymethoxy)benzene
• 英文别名: 5-Bromo-2-(methoxymethoxy)-1,3-di(propan-2-yl)benzene
• CAS: 168196-99-4
• 化学式: C₁₄H₂₁BrO₂
• 分子量: 301.224
• InChiKey: ASBGHBBLBZXHMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  34-36 °C
• 沸点：
  344.8±42.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-1,3-diisopropyl-2-(methoxymethoxy)benzene 在 四(三苯基膦)钯 、 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Pd 催化苯酚不对称环脱芳构化用于区域和对映选择性合成螺环己二酮

  摘要：

  据报道，钯催化的苯酚与丁烯二碳酸酯的不对称环环脱芳构化反应能够实现双重脱羧烯丙基化，从而区域选择性地产生一系列螺环己二酮，产率为 29-95%，ee 为 74-99%。1,1'-联苯-2,4'-二醇的催化脱芳香形式[4 + 2]环化生成螺[苯并二氢吡喃-4,1'-环己烷]-2',5'-二烯-4'-酮高对映选择性，而对映体富集的螺[环己烷-1,4'-喹啉]-2,5-二烯-4-酮是从2'-氨基-[1,1'-联苯]-4-醇开始生成的，为1， 4-双亲核试剂。

  DOI：

  10.1021/acs.orglett.3c02051
• 作为产物：
  描述：

  丙泊酚 在 溴 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 5-bromo-1,3-diisopropyl-2-(methoxymethoxy)benzene
  参考文献：
  名称：

  Pd 催化苯酚不对称环脱芳构化用于区域和对映选择性合成螺环己二酮

  摘要：

  据报道，钯催化的苯酚与丁烯二碳酸酯的不对称环环脱芳构化反应能够实现双重脱羧烯丙基化，从而区域选择性地产生一系列螺环己二酮，产率为 29-95%，ee 为 74-99%。1,1'-联苯-2,4'-二醇的催化脱芳香形式[4 + 2]环化生成螺[苯并二氢吡喃-4,1'-环己烷]-2',5'-二烯-4'-酮高对映选择性，而对映体富集的螺[环己烷-1,4'-喹啉]-2,5-二烯-4-酮是从2'-氨基-[1,1'-联苯]-4-醇开始生成的，为1， 4-双亲核试剂。

  DOI：

  10.1021/acs.orglett.3c02051

文献信息

• Discovery of novel soluble crystalline anesthetics
  申请人：Brown L. Milton

  公开号：US20070043121A1

  公开（公告）日：2007-02-22

  The invention discloses compounds derived from propofal which have greater aqueous solubility than propofal and are useful as anesthetic agents. The invention further discloses methods of preparing compounds of the invention. The invention also discloses methods of inducing anesthesia in a subject by administering compounds of the invention to the subject.

  该发明揭示了从异丙酚衍生的化合物，其比异丙酚具有更大的水溶性，并且可用作麻醉剂。该发明进一步揭示了制备该发明化合物的方法。该发明还揭示了通过向受试者施用该发明化合物来诱导受试者麻醉的方法。
• Comparative molecular field analysis and synthetic validation of a hydroxyamide-propofol binding and functional block of neuronal voltage-dependent sodium channels
  作者：Milton L. Brown、Hilary A. Eidam、Mikell Paige、Paulianda J. Jones、Manoj K. Patel

  DOI：10.1016/j.bmc.2008.11.069

  日期：2009.10

  Voltage gated sodium channels represent an important therapeutic target for a number of neurological disorders including epilepsy. Unfortunately, medicinal chemistry strategies for discovering new classes of antagonist for trans-membrane ion channels have been limited to mostly broad screening compound arrays. We have developed new sodium channel antagonist based on a propofol scaffold using the ligand based strategy of comparative molecular field analysis (CoMFA). The resulting CoMFA model was correlated and validated to provide insights into the design of new antagonists and to prioritize synthesis of these new structural analogs (compounds 4 and 5) that satisfied the steric and electrostatic model. Compounds 4 and 5 were evaluated for [H-3]-batrachotoxinin-A-20-alpha-benzoate ([H-3]-BTX-B) displacement yielding IC50's of 22 and 5.7 mu M, respectively. We further examined the potency of these two compounds to inhibit neuronal sodium currents recorded from cultured hippocampal neurons. At a concentration of 50 mu M, compounds 4 and 5 tonically inhibited sodium channels currents by 59 +/- 7.8% (n = 5) and 70 +/- 7.5% (n = 7), respectively. This clearly demonstrates that these compounds functionally antagonize native neuronal sodium channel currents. In summary, we have shown that CoMFA can be effectively used to discover new classes of sodium channel antagonists. (C) 2008 Elsevier Ltd. All rights reserved.
• Substituent‐Controlled Regiodivergent Palladium‐Catalyzed Annulative Dearomatization of Phenols toward Skeletally Diverse Spirocyclohexadienones
  作者：Hui‐Lin Mao、Jun Yu、Yi‐Ting Shen、Qiuyun Li、Wen‐Juan Hao、Bo Jiang

  DOI：10.1002/adsc.202300674

  日期：2023.9.19

  A palladium-catalyzed intermolecular dearomative formal [4+2] annulation of phenols with propargyl electrophiles is reported, enabling substituent-controlled regiodivergent synthesis of a wide range of skeletally diverse spirocyclohexadienones with good yields. The regiodivergence could be precisely controlled by adjusting the steric hindrance of O- and N-substituents from binucleophilic substrates

  报道了一种钯催化的苯酚与炔丙基亲电子试剂的分子间脱芳香形式[4+2]成环反应，使得取代基控制的区域发散合成多种骨架多样的螺环己二烯酮具有良好的产率。通过调节双亲核底物中O - 和N - 取代基的空间位阻可以精确控制区域发散，其中具有O - 亲核位点的底物被转化为螺[色烷-4,1'-环己烷]-2',5' -dien-4'-ones 具有完全的区域选择性和 ( Z )-选择性，而N-亲核试剂能够通过不同的区域发散过程来获得螺[环己烷-1,4'-喹啉]-2,5-dien-4-ones。
• Pd-Catalyzed Asymmetric Annulative Dearomatization of Phenols for Regio- and Enantioselective Synthesis of Spirocyclohexadienones
  作者：Hui-Lin Mao、Yu-Xin Wang、Xue Wang、Hai-Ying Wang、Wen-Juan Hao、Bo Jiang

  DOI：10.1021/acs.orglett.3c02051

  日期：2023.8.18

  A palladium-catalyzed asymmetric annulative dearomatization of phenols with butene dicarbonate is reported, enabling twofold decarboxylative allylation to regioselectively produce a range of spirocyclohexadienones with 29–95% yields and 74–99% ee. A catalytic dearomative formal [4 + 2] cyclization of 1,1′-biphenyl-2,4′-diols delivered spiro[chromane-4,1′-cyclohexane]-2′,5′-dien-4′-ones with high enantioselectivity

  据报道，钯催化的苯酚与丁烯二碳酸酯的不对称环环脱芳构化反应能够实现双重脱羧烯丙基化，从而区域选择性地产生一系列螺环己二酮，产率为 29-95%，ee 为 74-99%。1,1'-联苯-2,4'-二醇的催化脱芳香形式[4 + 2]环化生成螺[苯并二氢吡喃-4,1'-环己烷]-2',5'-二烯-4'-酮高对映选择性，而对映体富集的螺[环己烷-1,4'-喹啉]-2,5-二烯-4-酮是从2'-氨基-[1,1'-联苯]-4-醇开始生成的，为1， 4-双亲核试剂。