2-propenyl (3S,5R,6R)-2,2-dimethyl-6-(phenylacetamido)-7-oxopenam-3-carboxylate | 80127-23-7

• 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: 2-propenyl (3S,5R,6R)-2,2-dimethyl-6-(phenylacetamido)-7-oxopenam-3-carboxylate
• 英文别名: Penicillin G allyl ester；allyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate；benzylpenicillin-allyl ester；prop-2-enyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 80127-23-7
• 化学式: C₁₉H₂₂N₂O₄S
• 分子量: 374.461
• InChiKey: QTIZQDRJBWCMDC-HLLBOEOZSA-N

物化性质

• 沸点：
  616.7±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-propenyl (3S,5R,6R)-2,2-dimethyl-6-(phenylacetamido)-7-oxopenam-3-carboxylate 以93%的产率得到
  参考文献：
  名称：

  DEZIEL, ROBERT, TETRAHEDRON LETT., 28,(1987) N 38, 4371-4372

  摘要：

  DOI：
• 作为产物：
  描述：

  烯丙醇 、 benzylpenicillin-(carbonic acid ethyl ester)-anhydride 在 氯仿 、 三乙胺 作用下， 生成 2-propenyl (3S,5R,6R)-2,2-dimethyl-6-(phenylacetamido)-7-oxopenam-3-carboxylate
  参考文献：
  名称：

  Barnden et al., Journal of the Chemical Society, 1953, p. 3733,3736, 3737

  摘要：

  DOI：

文献信息

• Phase-Transfer Esterification of the Alkali Metal Salts of Cephalosporins and Penicillins
  作者：Iñaki Ganboa、Claudio Palomo

  DOI：10.1055/s-1986-31474

  日期：——

  Cephalosporins and penicillins can be converted into their alkyl esters in high yields by reaction of their solid sodium or potassium salts with alkyl bromides in acetonitrile in the presence of crown ethers as phase-transfer catalysts.

  在冠醚作为相转移催化剂的存在下，头孢菌素类和青霉素类的固体钠盐或钾盐与烷基溴化物在乙腈中发生反应，可以高产率地转化为它们的烷基酯。
• COMPOSITION FOR HARDENING SOFT TISSUE
  申请人：THE CATHOLIC UNIVERSITY OF KOREA INDUSTRY-ACADEMIC COOPERATION FOUNDATION

  公开号：US20190315770A1

  公开（公告）日：2019-10-17

  The present invention relates to various compounds capable of temporarily hardening soft tissue for surgical suturing of the soft tissue. The compounds according to the present invention can temporarily increase the hardness or tension of soft tissue, thereby improving the suturing efficiency during suturing of the soft tissue, thereby preventing aftereffects or the like from occurring due to insufficient anastomosis. In addition, the compounds according to the present invention can temporarily increase the hardness or tension of soft tissue, particularly pancreas, thereby increasing the suturing efficiency during pancreaticoduodenectomy and effectively preventing pancreatic leakage.

  本发明涉及各种能够暂时硬化软组织以进行软组织缝合的化合物。根据本发明的化合物可以暂时增加软组织的硬度或张力，从而在缝合软组织时提高缝合效率，防止由于吻合不足而产生的后遗症或类似问题的发生。此外，根据本发明的化合物可以暂时增加软组织，特别是胰腺的硬度或张力，从而在胰十二指肠切除术期间提高缝合效率并有效预防胰液漏出。
• Photosensitized O ₂ enables intermolecular alkene cyclopropanation by active methylene compounds
  作者：Dhruba P. Poudel、Amrit Pokhrel、Raj Kumar Tak、Majji Shankar、Ramesh Giri

  DOI：10.1126/science.adg3209

  日期：2023.8.4

  Cyclopropanes are key features in many preclinical, clinical, and commercial drugs, as well as natural products. The most prolific technique for their synthesis is the metal-catalyzed reaction of an alkene with a diazoalkane, a highly energetic reagent requiring stringent safety precautions. Discovery of alternative innocuous reagents remains an ongoing challenge. Herein, we report a simple photoredox-catalyzed

  环丙烷是许多临床前、临床和商业药物以及天然产物的关键特征。最丰富的合成技术是烯烃与重氮烷的金属催化反应，重氮烷是一种高能试剂，需要严格的安全预防措施。发现替代的无害试剂仍然是一个持续的挑战。在此，我们报道了未活化烯烃与活性亚甲基化合物的简单光氧化还原催化分子间环丙烷化反应。反应在中性溶剂中在空气或分子氧（O 2 ）与由蓝色发光二极管光激发的光氧化还原催化剂和碘助催化剂（以分子碘形式添加或由烷基碘原位生成）。机理研究表明光敏 O 2在活性亚甲基化合物与烯烃的加成和环闭合过程中碳中心自由基的生成中起着至关重要的作用。
• Composition for hardening soft tissue
  申请人：THE CATHOLIC UNIVERSITY OF KOREA INDUSTRY-ACADEMIC COOPERATION FOUNDATION

  公开号：US10745417B2

  公开（公告）日：2020-08-18

  The present invention relates to various compounds capable of temporarily hardening soft tissue for surgical suturing of the soft tissue. The compounds according to the present invention can temporarily increase the hardness or tension of soft tissue, thereby improving the suturing efficiency during suturing of the soft tissue, thereby preventing aftereffects or the like from occurring due to insufficient anastomosis. In addition, the compounds according to the present invention can temporarily increase the hardness or tension of soft tissue, particularly pancreas, thereby increasing the suturing efficiency during pancreaticoduodenectomy and effectively preventing pancreatic leakage.

  本发明涉及能够暂时硬化软组织的各种化合物，用于软组织的外科缝合。根据本发明的化合物可以暂时增加软组织的硬度或张力，从而在缝合软组织时提高缝合效率，防止因吻合不足而产生后遗症等。此外，根据本发明的化合物可以暂时增加软组织尤其是胰腺的硬度或张力，从而提高胰十二指肠切除术的缝合效率，有效防止胰腺渗漏。
• Homogeneous, palladium(0)-catalyzed exchange deprotection of allylic esters, carbonates and carbamates
  作者：Paul D. Jeffrey、Stuart W. McCombie

  DOI：10.1021/jo00342a048

  日期：1982.1