trifluoromethanesulfonic acid 2-cyano-1-cyclopenten-1-yl ester | 141754-28-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trifluoromethanesulfonic acid 2-cyano-1-cyclopenten-1-yl ester
• 英文别名: 2-cyanocyclopent-1-en-1-yl trifluoromethanesulfonate；(2-Cyanocyclopenten-1-yl) trifluoromethanesulfonate
• CAS: 141754-28-1
• 化学式: C₇H₆F₃NO₃S
• 分子量: 241.191
• InChiKey: BCWOTBOVVUIHFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  67.16
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trifluoromethanesulfonic acid 2-cyano-1-cyclopenten-1-yl ester 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 四(三苯基膦)钯 、 四溴化碳 、 四丁基氟化铵 、 sodium hydride 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 49.0h， 生成 2-<4-<<2-butyl-4-chloro-5-formyl-1H-imidazol-1-yl>methyl>phenyl>-1-cyclopentene-1-carbonotrile
  参考文献：
  名称：

  Nonpeptide angiotensin II receptor antagonists: synthetic and computational chemistry of N-[[4-[2-(2H-tetrazol-5-yl)-1-cycloalken-1-yl]phenyl]methyl]imidazole derivatives and their in vitro activity

  摘要：

  A series of nonpeptide angiotensin II receptor antagonists was synthesized and tested in vitro to investigate requirements for recognition by and binding to AT1 receptors. Compared to a known series of N-(biphenylylmethyl)imidazoles, including losartan (DuP 753), which has a more rigid conformation in the 2-tetrazolylbiphenyl moiety, the new series replaces the terminal phenyl with cycloalkenyls. Compounds were made with five- to seven-membered rings and with either a hydroxymethyl (3) or carboxyl (4) group at the 5 position on the imidazole ring. The effects of the lipophilicity and steric bulk of the terminal ring system, the amount of pi-electron density in the terminal ring, and the relative spatial proximity of the tetrazolyl and the middle phenyl are explored in terms of binding affinity to AT1 receptors in rat adrenal glomerulosa and rabbit aorta. The physicochemical variables of the new compounds were quantitated by computational chemistry and compared to those of losartan and its carboxyl metabolite. Potency at the AT1 receptors is maximized when the terminal ring is six-membered; an aromatic ring binds better than a cycloalkenyl ring. The 5-carboxyimidazole compounds show higher affinity than the 5-hydroxymethyl series.

  DOI：

  10.1021/jm00092a017
• 作为产物：
  描述：

  三氟甲磺酸酐 、 2-氰基环戊酮 在 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以77%的产率得到trifluoromethanesulfonic acid 2-cyano-1-cyclopenten-1-yl ester
  参考文献：
  名称：

  Nonpeptide angiotensin II receptor antagonists: synthetic and computational chemistry of N-[[4-[2-(2H-tetrazol-5-yl)-1-cycloalken-1-yl]phenyl]methyl]imidazole derivatives and their in vitro activity

  摘要：

  A series of nonpeptide angiotensin II receptor antagonists was synthesized and tested in vitro to investigate requirements for recognition by and binding to AT1 receptors. Compared to a known series of N-(biphenylylmethyl)imidazoles, including losartan (DuP 753), which has a more rigid conformation in the 2-tetrazolylbiphenyl moiety, the new series replaces the terminal phenyl with cycloalkenyls. Compounds were made with five- to seven-membered rings and with either a hydroxymethyl (3) or carboxyl (4) group at the 5 position on the imidazole ring. The effects of the lipophilicity and steric bulk of the terminal ring system, the amount of pi-electron density in the terminal ring, and the relative spatial proximity of the tetrazolyl and the middle phenyl are explored in terms of binding affinity to AT1 receptors in rat adrenal glomerulosa and rabbit aorta. The physicochemical variables of the new compounds were quantitated by computational chemistry and compared to those of losartan and its carboxyl metabolite. Potency at the AT1 receptors is maximized when the terminal ring is six-membered; an aromatic ring binds better than a cycloalkenyl ring. The 5-carboxyimidazole compounds show higher affinity than the 5-hydroxymethyl series.

  DOI：

  10.1021/jm00092a017

文献信息

• Unraveling the C₂-Symmetric Azatetraquinane System. Simple, Enantioselective Syntheses
  作者：G. Sudhakar Reddy、D. Srinivas Reddy、E. J. Corey

  DOI：10.1021/acs.orglett.1c00387

  日期：2021.3.19

  Concise stereocontrolled synthetic routes to the C2-symmetric azatetraquinane 1 (or, also, the enantiomer) are described. The successful execution of the synthesis involved innovation in the methodology for [3+2] cycloaddition and stereochemical control.

  描述了到C 2对称的氮杂四喹烷1（或对映体）的立体控制合成路线。合成的成功实施涉及[3 + 2]环加成和立体化学控制方法的创新。