3-(3-hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester | 33577-97-8

• 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: 3-(3-hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester
• 英文别名: Methyl 3-(3-hydroxy-3-methylbut-1-yn-1-yl)benzoate；methyl 3-(3-hydroxy-3-methylbut-1-ynyl)benzoate
• CAS: 33577-97-8
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: UEDSNOSDKGZKNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester 在 四(三苯基膦)钯 正丁基锂 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 15.5h， 生成 3-(1-methoxycarbonyl-3-methyl-buta-1,2-dienyl)-benzoic acid methyl ester
  参考文献：
  名称：

  Efficient Synthesis of Maleimides and Carbazoles via Zn(OTf)₂-Catalyzed Tandem Annulations of Isonitriles and Allenic Esters

  摘要：

  Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.

  DOI：

  10.1021/ol7018086
• 作为产物：
  描述：

  3-溴苯甲酸甲酯 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯基膦 作用下， 以 四氢呋喃 、 三乙胺 为溶剂， 生成 3-(3-hydroxy-3-methylbut-1-ynyl)benzoic acid methyl ester
  参考文献：
  名称：

  硫代吡罗宁的脱硫 Sonogashira 交叉偶联用于合成含近红外芳基乙炔的罗丹明

  摘要：

  首次通过硫代吡罗宁的脱硫 Sonogashira 交叉偶联反应开发了一种经典、安全且高效的红移策略，有助于产生近红外芳基乙炔含罗丹明，该策略具有广泛的底物范围和良好的产率。此外，化合物3m显示出作为单线态氧探针的巨大应用潜力，证明了该方法的实用性。

  DOI：

  10.1039/d3cc05995b

文献信息

• New 2,4-Diamino-5-(2‘,5‘-substituted benzyl)pyrimidines as Potential Drugs against Opportunistic Infections of AIDS and Other Immune Disorders. Synthesis and Species-Dependent Antifolate Activity
  作者：Andre Rosowsky、Ronald A. Forsch、Carol Hopkins Sibley、Clark B. Inderlied、Sherry F. Queener

  DOI：10.1021/jm030438k

  日期：2004.3.1

  carboxyphenyl group linked to the benzyl moiety by a bridge of two or four atoms in length. The new analogues were all obtained from 2,4-diamino-5-(5'-iodo-2'-methoxybenzyl)pyrimidine via a Sonogashira reaction, followed, where appropriate, by catalytic hydrogenation. The new analogues were tested as inhibitors of DHFR from Pneumocystis carinii (Pc), Toxoplasma gondii (Tg), and Mycobacterium avium (Ma)

  在不断努力设计二氢叶酸还原酶（DHFR）的小分子抑制剂，该抑制剂结合了2,4-二氨基-5-（3'，4'，5'-三甲氧基苄基）嘧啶（trimethoprim，TMP）的酶结合选择性具有2,4-二氨基-5-甲基-6-（2'，5'-二甲氧基苄基）吡啶并[2,3-d]嘧啶（piritrexim，PTX）的效力，七个先前未描述的2,4-二氨基-5合成了-[[2'-甲氧基-5'-（取代的苄基）]嘧啶，其中在5'-位的取代基是通过两个或四个原子的桥连接至苄基部分的羧苯基。新的类似物全部通过Sonogashira反应从2，4-二氨基-5-（5'-碘-2'-甲氧基苄基）嘧啶获得，随后在适当的情况下通过催化氢化获得。测试了新的类似物作为卡氏肺孢子虫（Pc），弓形虫（Tg）和鸟分枝杆菌（Ma）的DHFR抑制剂，这三种常见的威胁生命的病原体在AIDS患者和因以下原因而导致免疫系统受损的个体中发现用免疫抑制化学疗法
• Rh(III)-Catalyzed Oxidative C–H Activation/Annulation of Salicylaldehydes with Masked Enynes for the Synthesis of Chromones
  作者：Bo Li、Jianping Zhu、Xia Zheng、Wenqing Ti、Yue Huang、Hequan Yao

  DOI：10.1021/acs.joc.2c02557

  日期：2023.1.6

  A rhodium(III)-catalyzed oxidative C–H activation/annulation of salicylaldehydes with propargylic acetates has been developed for the regioselective synthesis of 3-vinyl chromones in good yields with broad functional group tolerance. 3-Vinyl chromones were converted into biologically active benzo[c]xanthone by I2-mediated oxidative electrocyclization.

  已开发出一种铑 (III) 催化的氧化 C-H 活化/水杨醛与炔丙基乙酸酯的环化反应，用于区域选择性合成 3-乙烯基色酮，收率高，具有广泛的官能团耐受性。3-乙烯基色酮通过 I 2介导的氧化电环化作用转化为具有生物活性的苯并[ c ]氧杂蒽酮。
• Benzo[<i>e</i>]isoindole-1,3-diones as Potential Inhibitors of Glycogen Synthase Kinase-3 (GSK-3). Synthesis, Kinase Inhibitory Activity, Zebrafish Phenotype, and Modeling of Binding Mode
  作者：Haixia Zou、Liyan Zhou、Yuanzhen Li、Yi Cui、Hanbing Zhong、Zhengying Pan、Zhen Yang、Junmin Quan

  DOI：10.1021/jm9013373

  日期：2010.2.11

  Benzo[e]isoindole-1,3-dione derivatives were synthesized, and the effects on GSK-3 beta activity and zebrafish embryo growth were evaluated. A series of derivatives show obvious inhibitory activity against GSK-3 beta. The most potent inhibitor, 7,8-dimethoxy-5-methylbenzo[e]isoindole-1,3-dione (8a), shows nanomolar IC50 and obvious phenotype on zebrafish embryo growth associated with the inhibition of GSK-3 beta at low micromolar concentration. The interaction mode between 8a and GSK-3 beta was characterized by computational modeling.
• Synthesis of arylacetylenes by the sodium hydride catalyzed cleavage of 4-aryl-2-methyl-3-butyn-2-ols
  作者：Stephen J. Havens、Paul M. Hergenrother

  DOI：10.1021/jo00210a042

  日期：1985.5
• HAVENS, S. J.;HERGENROTHER, P. M., J. ORG. CHEM., 1985, 50, N 10, 1763-1765
  作者：HAVENS, S. J.、HERGENROTHER, P. M.

  DOI：——

  日期：——