1-Hydroxy-4-phenylazetidin-2-one | 141942-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-Hydroxy-4-phenylazetidin-2-one
• CAS: 141942-28-1
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: UPUNPNQSFNXVJX-UHFFFAOYSA-N

物化性质

• 沸点：
  321.8±45.0 °C(Predicted)
• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Hydroxy-4-phenylazetidin-2-one 、 2-萘磺酰氯 在 三乙胺 作用下， 生成 4-phenyl N-(2-naphthalenylsulfonyloxy)-2-azetidinone
  参考文献：
  名称：

  N-Sulfonyloxy-β-lactam Inhibitors for β-Lactamases

  摘要：

  Structure-function analysis with a series of N-sulfonyloxy beta-lactam molecules as inhibitors of beta-lactamases is reported. The best of these compounds acylate the active site of the class A TEM-1 beta-lactamase from Escherichia coli rapidly, and resist deacylation. Whereas acylation of the active site of the class C beta-lactamase from Enterobacter cloacae was not seen, these compounds function as competitive inhibitors of this enzyme. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00427-0
• 作为产物：
  描述：

  4-phenyl O-Cbz-2-azetidinone 在 Lindlar's catalyst 氢气 作用下， 反应 0.5h， 生成 1-Hydroxy-4-phenylazetidin-2-one
  参考文献：
  名称：

  N-Sulfonyloxy-β-lactam Inhibitors for β-Lactamases

  摘要：

  Structure-function analysis with a series of N-sulfonyloxy beta-lactam molecules as inhibitors of beta-lactamases is reported. The best of these compounds acylate the active site of the class A TEM-1 beta-lactamase from Escherichia coli rapidly, and resist deacylation. Whereas acylation of the active site of the class C beta-lactamase from Enterobacter cloacae was not seen, these compounds function as competitive inhibitors of this enzyme. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00427-0

文献信息

• Processes for the preparation of docetaxel
  申请人：Vu Phong

  公开号：US20060281932A1

  公开（公告）日：2006-12-14

  The present invention provides processes for the production of docetaxel. Docetaxel is produced by protecting the C(7) and the C(10) hydroxy groups of 10-DAB with a bridging silicon-based protecting group. The resulting 7,10-protected 10-DAB derivative is then derivatized and deprotected to form docetaxel.

  本发明提供了多西他赛的生产工艺。多西他赛的生产是通过使用基于硅的桥接保护基来保护10-DAB的C（7）和C（10）羟基。然后，得到的7,10-保护的10-DAB衍生物进行衍生化和去保护，以形成多西他赛。
• Processes for the preparation of paclitaxel
  申请人：Vu Phong

  公开号：US20060281933A1

  公开（公告）日：2006-12-14

  The present invention provides processes for the production of paclitaxel. Paclitaxel is produced by protecting the C(7) and the C(10) hydroxy groups of 10-DAB with a bridging silicon-based protecting group. The resulting 7,10-protected 10-DAB derivative is then derivatized and deprotected to form paclitaxel.

  本发明提供了生产紫杉醇的工艺。通过使用基于硅的桥接保护基保护10-DAB的C（7）和C（10）羟基，生产紫杉醇。然后将得到的7,10-保护的10-DAB衍生物进行衍生化和去保护，形成紫杉醇。
• Potent mechanism-based inhibition of the TEM-1 .beta.-lactamase by novel N-sulfonyloxy .beta.-lactams
  作者：Alexey Bulychev、Michael E. O'Brien、Irina Massova、Min Teng、Tracy A. Gibson、Marvin J. Miller、Shahriar Mobashery

  DOI：10.1021/ja00127a005

  日期：1995.6

  A novel class of N-sulfonyloxy beta-lactam molecules are described as potent mechanism-based inactivators for the bacterial TEM-1 beta-lactamase, a prototypic class A enzyme. These molecules inactivate the enzyme with k(inact)/K-i values in the range of 1-7 x 10(4) M(-1) s(-1) and partition ratios (i.e., k(cat)/k(inact)) of 2-7. The mechanism of action of these inactivators was investigated. These molecules acylate the active-site serine of the TEM-1 beta-lactamase, a process that results in the release of the sulfonate attached to the lactam nitrogen, giving rise to a proposed beta-amino cinnamoyl derivative as the inhibitory species. This species undergoes gradual hydrolysis with concomitant recovery of activity, the rate constants for which were evaluated.
• Mulengi, J. Kajima; Fatmi, N., Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 4, p. 257 - 260
  作者：Mulengi, J. Kajima、Fatmi, N.

  DOI：——

  日期：——
• PROCESSES FOR THE PREPARATION OF DOCETAXEL
  申请人：Florida State University Research Foundation, Inc.

  公开号：EP1891033A2

  公开（公告）日：2008-02-27