Tert-butyl (5-(4-methoxyphenyl)pent-4-yn-1-yl)carbamate | 905293-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Tert-butyl (5-(4-methoxyphenyl)pent-4-yn-1-yl)carbamate
• 英文别名: tert-butyl N-[5-(4-methoxyphenyl)pent-4-ynyl]carbamate
• CAS: 905293-01-8
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: XOBIZRBYCXKYET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl (5-(4-methoxyphenyl)pent-4-yn-1-yl)carbamate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 24.0h， 以92%的产率得到tert-butyl (5-(4-methoxyphenyl)pentyl)carbamate
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers:  Drugs for Cystic Fibrosis and Chronic Bronchitis

  摘要：

  Amiloride (1), the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogues of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent shortcircuit current than amiloride. Compounds 30-34 showed the greatest potency on ENaC with IC50 values below 10 nM. A regioselective difference in potency was found (compounds 30, 39, and 40), whereas no stereospecific (compounds 33, 34) difference in potency on ENaC was displayed. Lead compound 32 was 102-fold more potent and 5-fold less reversible than amiloride and displayed the lowest IC50 value ever reported for an ENaC blocker.

  DOI：

  10.1021/jm051134w
• 作为产物：
  描述：

  4-碘苯甲醚 、 N-(4-戊炔基)氨基甲酸叔丁酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 16.0h， 以82%的产率得到Tert-butyl (5-(4-methoxyphenyl)pent-4-yn-1-yl)carbamate
  参考文献：
  名称：

  铂催化的分子内炔烃 OH 和 NH 加成中的区域选择性影响。

  摘要：

  阐明了铂催化的分子内加氢烷氧基化中区域选择性的空间和电子驱动因素。发现了一个分支点，该分支点将过程分为 5-exo 和 6-endo 选择性过程，并且对于两种氧杂环都可以以良好的产率获得烯醇醚。主要影响来自电子效应，其中炔烃取代基诱导炔烃极化，从而导致杂原子优先攻击更缺电子的碳。在其他情况下研究电子效应，包括加氢酰氧基化和加氢胺化，尽管没有统一观察到，但方向性的类似趋势占主导地位。

  DOI：

  10.1021/acs.orglett.9b03557

文献信息

• Photoredox-Catalyzed Trifluoromethylative Intramolecular Cyclization: Synthesis of CF₃-Containing Heterocyclic Compounds
  作者：Hong Sik Han、Eun Hye Oh、Young-Sik Jung、Soo Bong Han

  DOI：10.1021/acs.orglett.8b00648

  日期：2018.4.6

  A general photoredox-catalyzed intramolecular cyclization was developed for the synthesis of trifluoromethylated heterocyclic compounds. The reaction proceeded smoothly under mild photocatalytic conditions with high functional group tolerance, allowing the preparation of oxygen-, sulfur-, or nitrogen-containing heterocycles of different sizes. The broad substrate scope demonstrated the complexity-building

  开发了一种一般的光氧化还原催化的分子内环化反应，用于合成三氟甲基化的杂环化合物。反应在温和的光催化条件下以高官能团耐受性顺利进行，可以制备不同大小的含氧，硫或氮的杂环。广泛的底物范围证明了该策略在提高复杂性方面的潜力。
• Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O–H and N–H Additions
  作者：Jeff P. Costello、Eric M. Ferreira

  DOI：10.1021/acs.orglett.9b03557

  日期：2019.12.20

  The steric and electronic drivers of regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. A branch point is found that divides the process between 5-exo and 6-endo selective processes, and enol ethers can be accessed in good yields for both oxygen heterocycles. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization

  阐明了铂催化的分子内加氢烷氧基化中区域选择性的空间和电子驱动因素。发现了一个分支点，该分支点将过程分为 5-exo 和 6-endo 选择性过程，并且对于两种氧杂环都可以以良好的产率获得烯醇醚。主要影响来自电子效应，其中炔烃取代基诱导炔烃极化，从而导致杂原子优先攻击更缺电子的碳。在其他情况下研究电子效应，包括加氢酰氧基化和加氢胺化，尽管没有统一观察到，但方向性的类似趋势占主导地位。
• Design, Synthesis, and Structure−Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers:  Drugs for Cystic Fibrosis and Chronic Bronchitis
  作者：Andrew J. Hirsh、Bruce F. Molino、Jianzhong Zhang、Nadezhda Astakhova、William B. Geiss、Bruce J. Sargent、Brian D. Swenson、Alexander Usyatinsky、Michael J. Wyle、Richard C. Boucher、Rick T. Smith、Andra Zamurs、M. Ross Johnson

  DOI：10.1021/jm051134w

  日期：2006.7.1

  Amiloride (1), the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogues of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent shortcircuit current than amiloride. Compounds 30-34 showed the greatest potency on ENaC with IC50 values below 10 nM. A regioselective difference in potency was found (compounds 30, 39, and 40), whereas no stereospecific (compounds 33, 34) difference in potency on ENaC was displayed. Lead compound 32 was 102-fold more potent and 5-fold less reversible than amiloride and displayed the lowest IC50 value ever reported for an ENaC blocker.