3-hydroxy-2-isopropylcyclopent-2-enone | 5857-26-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酸
• 英文名称: 3-hydroxy-2-isopropylcyclopent-2-enone
• 英文别名: 2-isopropyl-1,3-cyclopentanedione；2-isopropyl-1,3-cyclopentandione；2-Isopropyl-1,3-cyclopentandion；3-Hydroxy-2-(propan-2-yl)cyclopent-2-en-1-one；3-hydroxy-2-propan-2-ylcyclopent-2-en-1-one
• CAS: 5857-26-1
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: KRZBEWWSZFPJTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-isopropylcyclopent-2-enone 在 间氯过氧苯甲酸 作用下， 以 三乙胺 、 苯 为溶剂， 生成 2-isopropylidene-1,3-cyclopentanedione
  参考文献：
  名称：

  Methodologies for 2-alkylidene-1,3-cyclopentanediones

  摘要：

  DOI：

  10.1016/s0040-4039(01)91138-4
• 作为产物：
  描述：

  1,3-环戊二酮 、 丙酮 在 二氢吡啶 、 L-脯氨酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-hydroxy-2-isopropylcyclopent-2-enone
  参考文献：
  名称：

  Cyclopentane-1,3-dione: A Novel Isostere for the Carboxylic Acid Functional Group. Application to the Design of Potent Thromboxane (A2) Receptor Antagonists

  摘要：

  Cyclopentane-1,3-diones are known to exhibit pK(a) values typically in the range of carboxylic acids. To explore the potential of the cyclopentane-1,3-dione unit as a carboxylic acid isostere, the physical chemical properties of representative congeners were examined and compared with similar derivatives bearing carboxylic acid or tetrazole residues. These studies suggest that cyclopentane-1,3-diones may effectively substitute for the carboxylic acid functional group. To demonstrate the use of the cyclopentane-1,3-dione isostere in drug design, derivatives of a known thromboxane A(2) prostanoid (TP) receptor antagonist, 3-(3-(2-(4-chlorophenylsulfonamido)ethyl)phenyl)propanoic acid (12), were synthesized and evaluated in both functional and radioligand-binding assays. A series of mono- and disubstituted cyclopentane-1,3-dione derivatives (41-45) were identified that exhibit nanomolar IC50 and K-d values similar to 12. Collectively, these studies demonstrate that the cyclopentane-1,3-dione moiety comprises a novel isostere of the carboxylic acid functional group. Given the combination of the relatively strong acidity, tunable lipophilicity, and versatility of the structure, the cyclopentane-1,3-dione moiety may constitute a valuable addition to the palette of carboxylic acid isosteres.

  DOI：

  10.1021/jm200980u

文献信息

• Eaton, Philip E.; Bunnelle, William H.; Engel, Peter, Canadian Journal of Chemistry, 1984, vol. 62, p. 2612 - 2626
  作者：Eaton, Philip E.、Bunnelle, William H.、Engel, Peter

  DOI：——

  日期：——
• EATON, P. E.;BUNNELLE, W. H., TETRAHEDRON LETT., 1984, 25, N 1, 23-26
  作者：EATON, P. E.、BUNNELLE, W. H.

  DOI：——

  日期：——
• EATON, PH. E.;BUNNELLE, W. H.;ENGEL, P., CAN. J. CHEM., 1984, 62, N 11, 2612-2626
  作者：EATON, PH. E.、BUNNELLE, W. H.、ENGEL, P.

  DOI：——

  日期：——
• MOENOMYCIN BIOSYNTHESIS-RELATED COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：Walker Suzanne

  公开号：US20100279980A1

  公开（公告）日：2010-11-04

  The methods and compositions described herein relate to the identification, isolation, and characterization of genes which encode proteins useful for the biosynthesis of transglycosylase inhibitors such as moes. The methods and compositions also relate to the production of such proteins, and their use in the synthesis of moes, the expression of moes, and the production of modified moes.
• METHODS AND COMPOUNDS FOR IDENTIFYING GLYCOSYLTRANSFERASE INHIBITORS
  申请人：President and Fellows of Harvard College

  公开号：US20150079618A1

  公开（公告）日：2015-03-19

  The present invention provides moenomycin-based probe compounds of Formula (I) for use in screening inhibitors of bacterial glycosyltransferases. The present invention also provides bacterial glycosyltransferase screening assays using compounds of Formula (I).