3-甲氧基苄基异丁酯 | 177762-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-甲氧基苄基异丁酯
• 英文名称: 1-(isocyanomethyl)-3-methoxybenzene
• 英文别名: 3-methoxybenzyl isocyanide；3-Methoxybenzylisocyanide
• CAS: 177762-74-2
• 化学式: C₉H₉NO
• mdl: MFCD02664576
• 分子量: 147.177
• InChiKey: MSAGVJQUFPGWKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  13.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-甲氧基苄基异丁酯 在 10 wt% Pd(OH)2 on carbon 、 氢气 、 O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Structure-activity relationship and biochemical evaluation of novel fibroblast activation protein and prolyl endopeptidase inhibitors with α-ketoamide warheads

  摘要：

  DOI：

  10.1016/j.ejmech.2021.113717
• 作为产物：
  描述：

  N-(3-甲氧基苄基)甲酰胺 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.07h， 以85%的产率得到3-甲氧基苄基异丁酯
  参考文献：
  名称：

  异氰化物2.0

  摘要：

  异氰酸酯官能团由于其在类胡萝卜素和三键特征之间的二分法而具有亲核和亲电子末端碳，在有机化学中表现出不同寻常的反应性，例如在Ugi反应中。不幸的是，仅按比例使用几种异氰酸酯妨碍了有关该官能团引人入胜的反应性的新发现。具有多个官能团的多种异氰酸酯的合成漫长，效率低下，并使化学家暴露于危险的烟雾中。在这里，我们提出了一种创新的异氰酸酯合成方法，它通过避免在96孔微量滴定板中以0.2 mmol规模在0.5 mol克规模进行平行合成而避免的水后处理，克服了这些问题。我们方法的优势包括提高合成速度，在非常温和的条件下可以使用迄今为止从未有过的未知或高度反应性的异氰酸酯类，可以快速使用大量官能化的异氰酸酯，具有较高的收率，高纯度，经过验证的5个数量级以上的可扩展性，增加的安全性和较少的反应浪费，从而大大减少了环境脚印。例如，迄今为止认为是不稳定的2-异氰基嘧啶，2-酰基苯基异氰酸酯，甚至邻-异氰基苯甲醛

  DOI：

  10.1039/d0gc02722g

文献信息

• Nonprostanoid prostacyclin mimetics. 5. Structure-activity relationships associated with [3-[4-(4,5-diphenyl-2-oxazolyl)-5-oxazolyl]phenoxy]acetic acid
  作者：Nicholas A. Meanwell、Jeffrey L. Romine、Michael J. Rosenfeld、Scott W. Martin、Ashok K. Trehan、J. J. Kim Wright、Mary F. Malley、Jack Z. Gougoutas、Catherine L. Brassard

  DOI：10.1021/jm00076a018

  日期：1993.11

  cis-olefin moiety of 3 into various ring systems was examined. Incorporation of the cis-olefin of 3 into either an oxazole (26) or an unsubstituted pyrazole (35) heterocycle provided compounds that are equipotent with progenitor 3. However, the oxazole 11f, which is isomeric with 26, inhibits ADP-induced human platelet aggregation in vitro with an IC50 of 0.027 microM, 6-fold more potent than 3, 26, or

  顺式[[3- [2-（4,5-二苯基-2-恶唑基）乙烯基]苯氧基]乙酸（3）先前被鉴定为非前列腺素类前列环素（PGI2）模拟物，可有效抑制ADP诱导的人血小板聚集IC50为0.18 microM。作为进一步探索此类血小板抑制剂的结构活性关系并提供对非前列腺素类PGI2模拟药效团的进一步了解的努力的一部分，我们研究了将3的顺式-烯烃部分限制在各种环系统中的作用。将3的顺式烯烃引入到恶唑（26）或未取代的吡唑（35）杂环中，可提供与祖细胞3等效的化合物。但是，与26异构的恶唑11f抑制ADP诱导的人血小板。体外聚集，IC50为0.027 microM，效力是3的6倍，26或35。这些结果表明，11f的中心恶唑环的作用不只是提供与PGI2受体相互作用的最佳立体定义的简单支架。假定11f的中心杂环的氮原子与PGI2受体蛋白中的供体部分参与氢键形成，由于拓扑结构明显不同，这种相互作用对于26是不可用
• 3-Phenyl-Substituted Imidazo[1,5-<i>a</i>]quinoxalin-4-ones and Imidazo[1,5-<i>a</i>]quinoxaline Ureas That Have High Affinity at the GABA_A/Benzodiazepine Receptor Complex
  作者：E. Jon Jacobsen、Lindsay S. Stelzer、Kenneth L. Belonga、Donald B. Carter、Wha Bin Im、Vimala H. Sethy、Andrew H. Tang、Philip F. VonVoigtlander、James D. Petke

  DOI：10.1021/jm960070+

  日期：1996.1.1

  A series of imidazo[1,5-alpha]quinoxalin-4-ones and imidazo[1,5-alpha]quinoxaline ureas containing substituted phenyl groups at the 3-position was developed. Compounds within the imidazo-[1,5-alpha]quinoxaline urea series had high affinity for the GABA(A)/benzodiazepine receptor complex with varying in vitro efficacy, although most analogs were partial agonists as indicated by [S-35]TBPS and Cl- current ratios. Interestingly, a subseries of piperazine ureas was identified which had biphasic efficacy, becoming more antagonistic with increasing concentration. Analogs within the imidazo [1,5-alpha] quinoxalin-4-one series had substantially decreased binding affinity as compared to the quinoxaline urea series. These compounds ranged from antagonists to full agonists by in. vitro analysis, with several derivatives having roughly 4-fold greater intrinsic activity than diazepam as indicated by Cl- current measurement. Numerous compounds from both series were effective in antagonizing metrazole-induced seizures, consistent with anti-convulsant properties and possible anxiolytic activity. Most of the quinoxaline ureas and quinoxalin-4-ones were active in an acute electroshock physical dependence side effect assay in mice precluding further development.
• Synthesis of Tetrazole-substituted Spirocyclic γ-lactams by One-pot Azido-Ugi Reaction–cyclization
  作者：Vasiliy Yu. Stolyarenko、Anatoliy A. Evdokimov、Vladimir I. Shishkin

  DOI：10.1016/j.mencom.2013.03.020

  日期：2013.3

  1-Ethoxycarbonyl-1-(2-oxoethyl)cycloalkanes in the azido-Ugi reaction with primary amines, isocyanides and TMS-N-3 afford 3-(tetrazol-5-yl)-2-azaspiro [4.n]alkan-1-ones.
• One-Pot Synthesis of Imidazo[1,5-c]pyrimidine Derivatives from a 4,6-Dichloropyrimidine Derivative and Benzyl Isocyanides
  作者：Kazuhiro Kobayashi、Daiki Fujiwara、Yuuho Shigemura、Hidetaka Hiyoshi、Kazuto Umezu

  DOI：10.3987/com-16-13616

  日期：——

  A convenient method for the synthesis of imidazo[1,5-c]pyrimidine derivatives has been developed. Thus, benzyl isocyanides are treated with sodium hydride in DMF at 0 degrees C to generate the corresponding benzyl anions, which are allowed to react with 4,6-dichloro-2-(methylsulfanyl)pyrimidine (DCSMP) to afford 1-aryl-7-chloro-5-(methylsulfanypimidazo[1,5-c]pyrimidines in one pot in moderate yields.
• Cyanide Abstractions from Benzyl Isocyanides by Phenyl and Tri-<i>n</i>-Butyltin Radicals:  New Examples of S_H2 Reactions
  作者：Sung Soo Kim、Ki Woong Yang、Chang Soo Lee

  DOI：10.1021/jo940292k

  日期：1996.1.1