2-[(E)-(pyrid-4-yl)methylene]cyclohexanone trifluoroacetic acid salt

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[(E)-(pyrid-4-yl)methylene]cyclohexanone trifluoroacetic acid salt
• 英文别名: (2E)-2-(pyridin-4-ylmethylidene)cyclohexan-1-one;2,2,2-trifluoroacetic acid
• 化学式: C₂HF₃O₂*C₁₂H₁₃NO
• 分子量: 301.265
• InChiKey: AZPDVYDLICVJRA-LBEJWNQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(E)-(pyrid-4-yl)methylene]cyclohexanone trifluoroacetic acid salt 在 三氟甲磺酸三甲基硅酯 、 碳酸氢钠 、 三乙胺 作用下， 以 水 、 乙酸乙酯 、 异丙醇 、 乙腈 为溶剂， 反应 7.25h， 生成 (3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(6R)-2-{(E)-(pyrid-4-yl)methylene}-1-oxocyclohex-6-yl]azetidin-2-one
  参考文献：
  名称：

  Preparation of the Key Intermediate in the Synthesis of GV143253A:  The Anti-MRSA/E Injectable Trinem

  摘要：

  GV143253A is a broad-spectrum injectable beta-lactam belonging to the class of trinem antibiotics. A key intermediate (3S,4R)-3-[(1R)-1-(tert-butyldimethyl- silyloxy)ethyl]-4-[-(6'R)-2'-[(E)(pyrid-4yl)methylene]-1'-oxocyclohex-6'-yl]azetidin-2-one (10) was identified and synthesized via different enolate coupling approaches, using enol ether, lithium, sodium, magnesium, tin, zinc, zirconium, and titanium enolates. Among these approaches, the synthesis of (3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[-(6'R)-2'-[(E)-(pyrid-4yl)-methylene]-1'-oxo- cyclohex-6'-yl]azetidin-2-one (10) via a titanium enolate offered advantages in terms of greater diastereoselectivity, higher yield, robustness, and isolation of intermediates and was superior to the method previously used for preparing large quantities of drug substance for early development studies.

  DOI：

  10.1021/op020024l
• 作为产物：
  描述：

  三氟乙酸 、 2-(hydroxy(pyridin-4-yl)methyl)cyclohexanone 在 乙酸酐 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 环己烷 为溶剂， 反应 3.5h， 以64.7%的产率得到2-[(E)-(pyrid-4-yl)methylene]cyclohexanone trifluoroacetic acid salt
  参考文献：
  名称：

  Preparation of the Key Intermediate in the Synthesis of GV143253A:  The Anti-MRSA/E Injectable Trinem

  摘要：

  GV143253A is a broad-spectrum injectable beta-lactam belonging to the class of trinem antibiotics. A key intermediate (3S,4R)-3-[(1R)-1-(tert-butyldimethyl- silyloxy)ethyl]-4-[-(6'R)-2'-[(E)(pyrid-4yl)methylene]-1'-oxocyclohex-6'-yl]azetidin-2-one (10) was identified and synthesized via different enolate coupling approaches, using enol ether, lithium, sodium, magnesium, tin, zinc, zirconium, and titanium enolates. Among these approaches, the synthesis of (3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[-(6'R)-2'-[(E)-(pyrid-4yl)-methylene]-1'-oxo- cyclohex-6'-yl]azetidin-2-one (10) via a titanium enolate offered advantages in terms of greater diastereoselectivity, higher yield, robustness, and isolation of intermediates and was superior to the method previously used for preparing large quantities of drug substance for early development studies.

  DOI：

  10.1021/op020024l

文献信息

• Tricyclic carbapenem compounds
  申请人：Glaxo Wellcome SpA

  公开号：US20010047094A1

  公开（公告）日：2001-11-29

  A compound of formula (1), salts and metabolically labile esters thereof, wherein R represents optionally substituted aryl or heteroaryl group; A represents a propylene chain or A is a chain of 3 members one of which is selected from an oxygen or sulphur atom orthe group NH or a substituted derivative thereof and the other two members are methylene groups, having antibacterial activity, processes for their preparation and to their use in medicine. 1

  公式（1）的化合物，其盐和代谢不稳定的酯，其中R代表可选取代的芳基或杂环基; A代表丙烯链或A是由3个成员组成的链，其中一个成员选自氧原子或硫原子或NH基团或其取代衍生物，另外两个成员是亚甲基基团，具有抗菌活性，其制备过程以及在医学上的应用。
• TRICYCLIC CARBAPENEM COMPOUNDS
  申请人：GLAXO WELLCOME S.p.A.

  公开号：EP0937078A1

  公开（公告）日：1999-08-25
• US6531466B2
  申请人：——

  公开号：US6531466B2

  公开（公告）日：2003-03-11
• [EN] TRICYCLIC CARBAPENEM COMPOUNDS<br/>[FR] COMPOSES CARBAPENEM
  申请人：GLAXO WELLCOME S.P.A.

  公开号：WO1998021210A1

  公开（公告）日：1998-05-22

  (EN) A compound of formula (I), salts and metabolically labile esters thereof, wherein R represents optionally substituted aryl or heteroaryl group; A represents a propylene chain or A is a chain of 3 members one of which is selected from an oxygen or sulphur atom or the group NH or a substituted derivative thereof and the other two members are methylene groups, having antibacterial activity, processes for their preparation and to their use in medicine.(FR) L'invention concerne un composé de la formule (I), des sels et des esters métaboliquement labiles dudit composé ayant une activité antibactérienne, ainsi que des procédés pour leur préparation et leur utilisation en médecine. Dans la formule, R représente un aryle éventuellement substitué ou un groupe hétéroaryle; A représente une chaîne propylène ou est une chaîne constituée de 3 éléments, dont l'un appartient au groupe constitué d'un atome d'oxygène, d'un atome de soufre, du groupe NH ou d'un dérivé substitué du groupe, les deux autres éléments étant des groupes méthylènes.
• Preparation of the Key Intermediate in the Synthesis of GV143253A:  The Anti-MRSA/E Injectable Trinem
  作者：Paolo Maragni、Mario Mattioli、Roberta Pachera、Alcide Perboni、Bruno Tamburini

  DOI：10.1021/op020024l

  日期：2002.9.1

  GV143253A is a broad-spectrum injectable beta-lactam belonging to the class of trinem antibiotics. A key intermediate (3S,4R)-3-[(1R)-1-(tert-butyldimethyl- silyloxy)ethyl]-4-[-(6'R)-2'-[(E)(pyrid-4yl)methylene]-1'-oxocyclohex-6'-yl]azetidin-2-one (10) was identified and synthesized via different enolate coupling approaches, using enol ether, lithium, sodium, magnesium, tin, zinc, zirconium, and titanium enolates. Among these approaches, the synthesis of (3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[-(6'R)-2'-[(E)-(pyrid-4yl)-methylene]-1'-oxo- cyclohex-6'-yl]azetidin-2-one (10) via a titanium enolate offered advantages in terms of greater diastereoselectivity, higher yield, robustness, and isolation of intermediates and was superior to the method previously used for preparing large quantities of drug substance for early development studies.