3-benzyl-5-(chloromethyl)-2-pyranone | 102587-00-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-benzyl-5-(chloromethyl)-2-pyranone
• 英文别名: 3-Benzyl-5-chloromethyl-pyran-2-one；3-benzyl-5-(chloromethyl)pyran-2-one
• CAS: 102587-00-8
• 化学式: C₁₃H₁₁ClO₂
• 分子量: 234.682
• InChiKey: LNHHIQKEPVFPAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-5-(chloromethyl)-2-pyranone 在 silver(I) acetate 、 溶剂黄146 、 锌 作用下， 反应 22.0h， 以51.8%的产率得到3-benzyl-5-methyl-2-pyranone
  参考文献：
  名称：

  5-(Halomethyl)-2-pyranones as irreversible inhibitors of .alpha.-chymotrypsin

  摘要：

  A series of 5-(halomethyl)-2-pyranones were prepared and assayed as potential mechanism-based inhibitors of chymotrypsin, in order to test whether substitution of a suitable electron-withdrawing group at position 5 in a 2-pyranone can activate the ring for catalytic hydrolysis, as well as form a mechanism-based inhibitor. 3-Benzyl-5-(chloromethyl)-2-pyranone (3) and 3-(1-naphthylmethyl)-5-(chloromethyl)-2-pyranone (4) rapidly and irreversibly inactivate chymotrypsin with high efficiency (I/E = 2.0 for 3 and 1.38 for 4). However, evidence for their formation of an acyl enzyme is lacking, and thus they may simply be active-site alkylating agents. 6-Methyl substitution on 4, or replacement of the chloromethyl of 3 with CF3, prevents inactivation. Since 6-bromo substitution is capable of ring activation, but 5-bromo substitution (3-benzyl-5-bromo-2-pyranone (11)) is not, the 5-position of the pyrone does not appear to affect catalytic hydrolysis.

  DOI：

  10.1021/jm00158a027
• 作为产物：
  描述：

  溴苯 、 3,5-Bis(chloromethyl)-2H-pyran-2-one 、 四氢呋喃 以10%的产率得到
  参考文献：
  名称：

  BOULANGER W. A.; KATZENELLENBOGEN J. A., J. MED. CHEM., 29,(1986) N 8, 1483-1487

  摘要：

  DOI：

文献信息

• Methods And Compositions For The Treatment Of Gastrointestinal disorders
  申请人：Currie Mark G.

  公开号：US20080025966A1

  公开（公告）日：2008-01-31

  The use of chymotrypsin inhibitors for treating various disorders, including IBS and other gastrointestinal disorders and conditions (e.g., gastrointestinal motility disorders, functional gastrointestinal disorders, gastroesophageal reflux disease (GERD), Crohn's disease, ulcerative colitis, inflammatory bowel disease, functional heartburn, dyspepsia (including functional dyspepsia or nonulcer dyspepsia), gastroparesis, chronic intestinal pseudo-obstruction (or colonic pseudoobstruction), and disorders and conditions associated with constipation is described.
• Methods and Compositions for the Treatment of Hypertension and Gastrointestinal Disorders
  申请人：Talley John Jeffrey

  公开号：US20090054319A1

  公开（公告）日：2009-02-26

  The use of guanylin potentiating agents for treating various disorders, including hypertension as well as IBS and other gastrointestinal disorders and conditions (e.g., gastrointestinal motility disorders, chronic intestinal pseudo-obstruction, colonic pseudo-obstruction, Crohn's disease, duodenogastric reflux, dyspepsia, functional dyspepsia, nonulcer dyspepsia, a functional gastrointestinal disorder, functional heartburn, gastroesophageal reflux disease (GERD), gastroparesis, inflammatory bowel disease, irritable bowel syndrome, post-operative ileus, ulcerative colitis, chronic constipation, and disorders and conditions associated with constipation is described.
• [EN] METHODS AND COMPOSITIONS FOR THE TREATMENT OF HYPERTENSION AND GASTROINTESTINAL DISORDERS<br/>[FR] METHODES ET COMPOSITIONS POUR LE TRAITEMENT DE L'HYPERTENSION ET DE TROUBLES GASTRO-INTESTINAUX
  申请人：MICROBIA INC

  公开号：WO2006102069A2

  公开（公告）日：2006-09-28

  [EN] The use of guanylin potentiating agents for treating various disorders, including hypertension as well as IBS and other gastrointestinal disorders and conditions (e.g., gastrointestinal motility disorders, chronic intestinal pseudo-obstruction, colonic pseudo-obstruction, Crohn's disease, duodenogastric reflux, dyspepsia, functional dyspepsia, nonulcer dyspepsia, a functional gastrointestinal disorder, functional heartburn, gastroesophageal reflux disease (GERD), gastroparesis, inflammatory bowel disease, irritable bowel syndrome, post-operative ileus, ulcerative colitis, chronic constipation, and disorders and conditions associated with constipation is described.
  [FR] L'invention porte sur l'utilisation d'agents potentialiseurs pour traiter différents troubles dont le syndrome du côlon irritable et d'autres troubles et états gastro-intestinaux tels que: les troubles de la motilité gastro-intestinale, la pseudo obstruction intestinale, la pseudo obstruction du côlon, la maladie de Crohn, le reflux duodénogastrique, la dyspepsie, la dyspepsie fonctionnelle, la dyspepsie non ulcéreuse, les troubles gastro-intestinaux fonctionnels, la pyrosis fonctionnelle, le reflux gastrooesophagien, la gastroparésie, l'inflammation de l'intestin, le syndrome de l'intestin irritable, l'occlusion intestinale post opératoire, la rectocolite hémorragique, la constipation chronique, et des troubles et états associés à la constipation.