1-异丙烯基-2,4-二甲氧基苯 | 17736-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-异丙烯基-2,4-二甲氧基苯
• 英文名称: 2,4-dimethoxy-1-(prop-1-en-2-yl)benzene
• 英文别名: 2,4-dimethoxy-α-methylstyrene；1-Isopropenyl-2,4-dimethoxybenzene；2,4-dimethoxy-1-prop-1-en-2-ylbenzene
• CAS: 17736-45-7
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: FXKKJKXHKNPZTP-UHFFFAOYSA-N

物化性质

• 沸点：
  170 °C(Press: 10 Torr)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  1-异丙烯基-2,4-二甲氧基苯 在 palladium 10% on activated carbon 、 氢气 、 tetra-N-butylammonium tribromide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 19.0h， 生成 1-bromo-5-isopropyl-2,4-dimethoxybenzene
  参考文献：
  名称：

  Discovery of 2-((4-resorcinolyl)-5-aryl-1,2,3-triazol-1-yl)acetates as potent Hsp90 inhibitors with selectivity over TRAP1

  摘要：

  As the most abundant heat shock protein (HSP), Hsp90 is actively involved in tumor cell growth and various responses to anti-carcinogenic stress. Hsp90 has thus emerged as a potential drug target. A structure-based drug design approach was applied to develop novel resorcinolyltriazole derivatives as Hsp90 inhibitors. Structure-activity relationships (SARs) and molecular docking were investigated to provide a rationale for binding affinity and paralog selectivity. Click chemistry between iodoethynylresorcinol and an azido derivative was used to synthesize a new family of 2-((4-resorcinolyl)-5-aryl-1,2,3-triazol-1-yl) acetates that exhibited Hsp90 binding affinities of 40-100 nM (IC50). Among the synthesized molecules, the triazole alkyl acetates displayed the highest Hsp90 binding affinities. Their potency against Hsp90 was over 100-fold stronger than against TRAP1 and 1-3-fold stronger than against Grp94. In particular, compounds 18, 19, and 30 had Hsp90 inhibitory activities of similar to 45 nM (IC50) and they displayed over 350-fold selectivity for Hsp90 over TRAP1.

  DOI：

  10.1016/j.bmcl.2019.126809
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 potassium carbonate 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 1.0h， 生成 1-异丙烯基-2,4-二甲氧基苯
  参考文献：
  名称：

  基于取代的 2-羟基苯甲醇的无环和环状膦酸酯的合成

  摘要：

  从水杨醛、水杨酸的衍生物中方便地合成苄基膦酸酯和芳环取代的 2,3-二氢苯并[d][1,2]氧杂磷酰 2-氧化物，以及它们的前体，2-羟基苄醇和 2-羟基苯乙酮在芳环的对位带有一个额外的羟基或甲氧基。首次显示了选择性去甲基化位于亚甲基膦酸酯片段邻位的甲氧基的可能性，而甲氧基保留在对位。

  DOI：

  10.1007/s11172-020-3013-2

文献信息

• Tertiary and Quaternary Carbon Formation via Gallium-Catalyzed Nucleophilic Addition of Organoboronates to Cyclopropanes
  作者：Truong N. Nguyen、Jeremy A. May

  DOI：10.1021/acs.orglett.7b03349

  日期：2018.1.5

  via homoconjugate addition of organoboron nucleophiles to diester- and ketone-functionalized cyclopropanes. Electron donor group cyclopropane substituents were not needed, allowing electron-deficient aryl, alkenyl, alkyl, and hydrogen-substituted cyclopropanes to be used. The catalytic conditions were compatible with alkenyl, alkynyl, and aryl nucleophiles, including ortho-substituted aromatics, to

  GaCl 3和（IPr）GaCl 3 / AgSbF 6通过将有机硼亲核试剂均相加成到二酯和酮官能化的环丙烷上而形成γ-叔碳和γ-季碳。不需要电子供体基团的环丙烷取代基，从而可以使用缺电子的芳基，烯基，烷基和氢取代的环丙烷。催化条件与烯基，炔基和芳基亲核试剂（包括邻位取代的芳族化合物）相容，以合成高度受阻的季碳。炔基亲核试剂形成取代的环戊烯。对照实验支持季碳中心形成中的中间碳正离子化。
• Iron-catalyzed olefin hydrogenation at 1 bar H₂ with a FeCl₃–LiAlH₄ catalyst
  作者：Tim N. Gieshoff、Matteo Villa、Alice Welther、Markus Plois、Uttam Chakraborty、Robert Wolf、Axel Jacobi von Wangelin

  DOI：10.1039/c4gc02368d

  日期：——

  The scope and mechanism of a practical protocol for the iron-catalyzed hydrogenation of alkenes and alkynes at 1 bar H₂ pressure were studied.

  研究了在1巴氢气压力下，铁催化的烯烃和炔烃氢化的实际协议的范围和机制。

• Visible-Light-Promoted Regioselective 1,3-Fluoroallylation of <i>gem</i>-Difluorocyclopropanes
  作者：Haidong Liu、Yi Li、Ding-Xing Wang、Meng-Meng Sun、Chao Feng

  DOI：10.1021/acs.orglett.0c03268

  日期：2020.11.6

  A strategically novel protocol for ring-opening functionalization of aryl gem-difluorocyclopropanes (F2CPs), which allows an expedient construction of CF3-containing architectures via visible-light-promoted F-nucleophilic attack manifold, was disclosed. Single electron oxidation of F2CPs was ascribed as the critical step for the success of this transformation by prompting F-nucleophilic attack, as

  公开了用于芳基宝石-二氟环丙烷（F 2 CP）的开环官能化的策略上新颖的协议，其允许通过可见光促进的F-亲核攻击歧管方便地构建含CF 3的结构。F 2 CP的单电子氧化被认为是通过促进F亲核攻击以及随之而来的C–C键断裂而成功实现该转化的关键步骤。通过调用宝石-二氟取代基的阳离子稳定性质，以及通过形成CF 3获得的热力学增益，可以合理化观察到的对于该反应中的氟掺入的区域选择性。功能。通过使用经济有效的氟化试剂和易于获得的底物，可以以通常良好的收率获得广泛的结构多样化的α-烯丙基-β-三氟甲基乙苯衍生物。进一步的机械研究证明，苄基自由基中间体参与了该转化。
• Thermally Induced Carbohydroxylation of Styrenes with Aryldiazonium Salts
  作者：Stephanie Kindt、Karina Wicht、Markus R. Heinrich

  DOI：10.1002/anie.201601656

  日期：2016.7.18

  The radical carbohydroxylation of styrenes with aryldiazonium salts has been achieved under mild thermal conditions. A broad range of aryldiazonium salts was tolerated, and the reaction principle based on a radical-polar crossover mechanism could be extended to carboetherification as well as to a two-step, metal-free variant of the Meerwein arylation leading to stilbenes.

  苯乙烯与芳基重氮盐的自由基碳羟基化已在温和的热条件下实现。可以耐受多种芳基重氮盐，并且基于自由基-极性交叉机制的反应原理可以扩展到碳醚化以及产生茋的Meerwein芳基化的两步、无金属变体。
• Branched-Selective Decarboxylative Heck Reaction with Electronically Unbiased Olefins
  作者：Jianchen Shen、Biping Xu、Min Zhang、Weiping Su

  DOI：10.1002/ejoc.201800330

  日期：2018.6.15

  We describe the PdII‐catalyzed decarboxylative Heck reaction of aromatic carboxylic acids with an array of electronically unbiased olefins, which leads to the regioselective formation of less common branched products in good yield. The use of inexpensive, stable, and readily available aromatic carboxylic acids as aryl reagents, make this method attractive for the synthesis of useful α‐alkyl vinylarenes

  我们描述了芳族羧酸与一系列电子无偏烯烃的Pd II催化的脱羧Heck反应，这导致了不常见的支化产物的区域选择性形成，收率很高。使用廉价，稳定且易于获得的芳族羧酸作为芳基试剂，使该方法对合成有用的α-烷基乙烯基芳烃具有吸引力。