3-amino-4,4-dimethyl-2-cyclohexene-1-one | 315188-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-amino-4,4-dimethyl-2-cyclohexene-1-one
• 英文别名: 3-amino-4,4-dimethylcyclohex-2-enone；3-amino-4,4-dimethyl-2-cyclohexen-1-one；3-Amino-4.4-dimethyl-2-cyclohexen-1-one；3-amino-4,4-dimethylcyclohex-2-en-1-one
• CAS: 315188-36-4
• 化学式: C₈H₁₃NO
• mdl: MFCD19207557
• 分子量: 139.197
• InChiKey: SMKMXSKKMKIROO-UHFFFAOYSA-N

物化性质

• 沸点：
  216.3±30.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-amino-4,4-dimethyl-2-cyclohexene-1-one 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 105.0h， 生成 9-(3-bromo-4-fluorophenyl)-5,5-dimethyl-2,3,5,6,7,9-hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-dioxide
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a Novel Series of 2,3,5,6,7,9-Hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide K_ATP Channel Openers:  Discovery of (−)-(9S)-9-(3-Bromo-4-fluorophenyl)-2,3,5,6,7,9- hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide (A-278637), a Potent K_ATP Opener That Selectively Inhibits Spontaneous Bladder Contractions

  摘要：

  Structure-activity relationships were investigated on a novel series of sulfonyldihydropyridine-containing K-ATP openers. Ring sizes, absolute stereochemistry, and aromatic substitution were evaluated for K-ATP activity in guinea pig bladder cells using a fluorescence-based membrane potential assay and in a pig bladder strip assay. The inhibition of spontaneous bladder contractions in vitro was also examined for a select group of compounds. All compounds studied showed greater potency to inhibit spontaneous bladder contractions relative to their potencies to inhibit contractions elicited by electrical stimulation. In an anesthetized pig model of myogenic bladder overactivity, compound 14 and (-)-cromakalim 1 were found to inhibit spontaneous bladder contractions in vivo at plasma concentrations lower than those that affected hemodynamic parameters. Compound 14 showed approximately 5-fold greater selectivity than I in vivo and supports the concept that bladder-selective K-ATP channel openers may have utility in the treatment of overactive bladder.

  DOI：

  10.1021/jm030356w
• 作为产物：
  描述：

  3-methoxy-4,4-dimethylcyclohex-2-enone 在 氨 作用下， 100.0 ℃ 、5.86 MPa 条件下， 反应 34.0h， 以1.14 g的产率得到3-amino-4,4-dimethyl-2-cyclohexene-1-one
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of a Novel Series of 2,3,5,6,7,9-Hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide K_ATP Channel Openers:  Discovery of (−)-(9S)-9-(3-Bromo-4-fluorophenyl)-2,3,5,6,7,9- hexahydrothieno[3,2-b]quinolin-8(4H)-one 1,1-Dioxide (A-278637), a Potent K_ATP Opener That Selectively Inhibits Spontaneous Bladder Contractions

  摘要：

  Structure-activity relationships were investigated on a novel series of sulfonyldihydropyridine-containing K-ATP openers. Ring sizes, absolute stereochemistry, and aromatic substitution were evaluated for K-ATP activity in guinea pig bladder cells using a fluorescence-based membrane potential assay and in a pig bladder strip assay. The inhibition of spontaneous bladder contractions in vitro was also examined for a select group of compounds. All compounds studied showed greater potency to inhibit spontaneous bladder contractions relative to their potencies to inhibit contractions elicited by electrical stimulation. In an anesthetized pig model of myogenic bladder overactivity, compound 14 and (-)-cromakalim 1 were found to inhibit spontaneous bladder contractions in vivo at plasma concentrations lower than those that affected hemodynamic parameters. Compound 14 showed approximately 5-fold greater selectivity than I in vivo and supports the concept that bladder-selective K-ATP channel openers may have utility in the treatment of overactive bladder.

  DOI：

  10.1021/jm030356w

文献信息

• Copper-Catalyzed Thiolation of Terminal Alkynes Employing Thiocyanate as the Sulfur Source Leading to Enaminone-Based Alkynyl Sulfides under Ambient Conditions
  作者：Chandran R.、Ashwini Pise、Suraj Kumar Shah、Rahul D.、Suman V.、Keshri Nath Tiwari

  DOI：10.1021/acs.orglett.0c02308

  日期：2020.8.21

  A highly efficient protocol for copper-catalyzed thio-alkynylation of enaminone-based thiocyanates with terminal alkynes under mild conditions has been developed. This scalable amino group-directed thio-alkynylation proceeds in the open air with a broad substrate scope and an excellent yield. The demonstrated synthetic transformation creates the opportunity for a wide variety of sulfur-containing useful

  已经开发了在温和条件下铜与氨基炔基硫氰酸酯的铜催化硫代炔基化反应的高效方法。这种可扩展的氨基导向的硫代-炔基化反应在露天进行，具有广泛的底物范围和优异的收率。证明的合成转化为各种各样的含硫有用材料创造了机会。炔基硫化物的克级合成和进一步的合成转化突出了该方法的潜在用途。
• Potassium channel openers
  申请人：Abbott Laboratories

  公开号：US06593335B1

  公开（公告）日：2003-07-15

  Compounds having the formula I: are useful in treating diseases prevented by or ameliorated with potassium channel openers. Also disclosed are potassium channel opening compositions and a method of opening potassium channels in a mammal.

  具有I式的化合物可用于治疗由钾通道开放剂预防或改善的疾病。还披露了开放钾通道的组合物和在哺乳动物中开放钾通道的方法。
• Electrosynthesis of Thiocyanated/Iodinated/Brominated Pyrazol‐5‐amines and Thiocyanated Enamines via C(<i>sp</i>²)−H Functionalization
  作者：Peng Qian、Siqi Jiang、Wenbao Zhang、Hui Zhang、Yuhan Ma、Na Li、Liangquan Sheng

  DOI：10.1002/adsc.202300255

  日期：2023.6.13

  An electrochemical method for the C(sp2)−H thiocyanation of pyrazol-5-amines and enamines were developed in an undivided cell. A variety of thiocyanated pyrazol-5-amine and enamine derivatives were accessed in 36–91% yields, employing thiocyanate salts as electrolyte and thiocyanating reagent. Moreover, this electrochemical protocol can be extended to the synthesis of various iodinated and brominated

  在未分隔的电池中开发了一种用于吡唑-5-胺和烯胺的C( sp 2 )-H 硫氰化的电化学方法。使用硫氰酸盐作为电解质和硫氰化试剂，以 36-91% 的收率获得了多种硫氰化吡唑-5-胺和烯胺衍生物。此外，该电化学方案可以扩展到以 51-95% 的收率合成各种碘化和溴化吡唑-5-胺衍生物。这种电化学协议不需要金属或外部化学氧化剂，并且可以容忍未受保护的氨基。
• Iron(III)-Catalyzed Amine-Release Triple Condensation of Enaminones to C3-Alkenylated Dihydroquinolinones
  作者：Qiaoqiao Wang、Xu Yuan、Haoyang Sun、Jimei Yang、Xingjiang Yang、Jun Lin、Yi Jin

  DOI：10.1021/acs.joc.4c00750

  日期：2024.8.2

  C3-functionalized dihydroquinolinones represent a class of important biologically active compounds. Although methods for synthesizing C2/4-functionalized dihydroquinolinones have been extensively reported, research on the synthesis of C3-functionalized dihydroquinolinone is extremely rare. Herein, we report for the first time a method for C3-alkenylated dihydroquinolinones via iron(III)-catalyzed amine-release

  C3-官能化二氢喹啉酮代表了一类重要的生物活性化合物。尽管C2/4功能化二氢喹啉酮的合成方法已被广泛报道，但C3功能化二氢喹啉酮的合成研究却极为罕见。在此，我们首次报道了一种通过铁（III）催化的烯胺释放胺三重缩合来制备C3-烯基化二氢喹啉酮的方法。这些反应表现出广泛的底物范围，并在一步中提供操作简单、低成本的催化程序。随后对烯烃部分进行分子内和分子间加成，提供多种 C3 官能化二氢喹啉酮衍生物。
• DIHYDROPYRIDINE COMPOUNDS AND METHODS OF USE
  申请人：ABBOTT LABORATORIES

  公开号：EP1131322A2

  公开（公告）日：2001-09-12