trans-3-(5-phenylpentyl)-4-tridecyloxetan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-3-(5-phenylpentyl)-4-tridecyloxetan-2-one
• 英文别名: trans-3-(5-Phenylpentyl)-4-tridecyloxetan-2-one；(3S,4S)-3-(5-phenylpentyl)-4-tridecyloxetan-2-one
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: SONUXALEEFVVGD-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  29
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  dimethyltitanocene 、 trans-3-(5-phenylpentyl)-4-tridecyloxetan-2-one 以 甲苯 为溶剂， 反应 5.0h， 以40%的产率得到trans-2-methylene-3-(5-phenylpentyl)-4-tridecyloxetane
  参考文献：
  名称：

  Combining cross-metathesis and activity-based protein profiling: New β-lactone motifs for targeting serine hydrolases

  摘要：

  beta-Lactones are a privileged structural motif as enzyme inhibitors and chemical probes, particularly for the inhibition of enzymes from the serine hydrolase class. Herein, we demonstrate that cross-metathesis (CM) of alpha-methylene-beta-lactones offers rapid access to structurally diverse, previously unexplored beta-lactones. Combining this approach with competitive activity-based protein profiling (ABPP) identified lead beta-lactone inhibitors/probes for several serine hydrolases, including disease-associated enzymes and enzymes of uncharacterized function. The structural diversity afforded by the alpha-methylene-beta-lactone scaffold thus expands the landscape of serine hydrolases that can be targeted by small-molecule inhibitors and should further the functional characterization of enzymes from this class through the optimization of target-selective probes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.038
• 作为产物：
  描述：

  肉豆蔻醛 在 三乙烯二胺 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium tetrahydroborate 、 双(三苯基膦)氯化钴 、 mercury(II) trifluoroacetate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 178.34h， 生成 trans-3-(5-phenylpentyl)-4-tridecyloxetan-2-one
  参考文献：
  名称：

  Combining cross-metathesis and activity-based protein profiling: New β-lactone motifs for targeting serine hydrolases

  摘要：

  beta-Lactones are a privileged structural motif as enzyme inhibitors and chemical probes, particularly for the inhibition of enzymes from the serine hydrolase class. Herein, we demonstrate that cross-metathesis (CM) of alpha-methylene-beta-lactones offers rapid access to structurally diverse, previously unexplored beta-lactones. Combining this approach with competitive activity-based protein profiling (ABPP) identified lead beta-lactone inhibitors/probes for several serine hydrolases, including disease-associated enzymes and enzymes of uncharacterized function. The structural diversity afforded by the alpha-methylene-beta-lactone scaffold thus expands the landscape of serine hydrolases that can be targeted by small-molecule inhibitors and should further the functional characterization of enzymes from this class through the optimization of target-selective probes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.038

文献信息

• LACTONE COMPOUNDS AND METHODS OF MAKING AND USING SAME
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：US20170313669A1

  公开（公告）日：2017-11-02

  Provided herein are lactone compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as inhibitors of serine hydrolases, such as ABHD16A. Furthermore, the subject compounds and compositions may be useful for the treatment of, for example, PHARC and other neuroinflammatory diseases.
• [EN] LACTONE COMPOUNDS AND METHODS OF MAKING AND USING SAME<br/>[FR] COMPOSÉS DE LACTONE, LEURS PROCÉDÉS DE PRÉPARATION ET D'UTILISATION
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2016069542A2

  公开（公告）日：2016-05-06

  Provided herein are lactone compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as inhibitors of serine hydrolases, such as ABHD16A. Furthermore, the subject compounds and compositions may be useful for the treatment of, for example, PHARC and other neuroinflammatory diseases.
• Combining cross-metathesis and activity-based protein profiling: New β-lactone motifs for targeting serine hydrolases
  作者：Kaddy Camara、Siddhesh S. Kamat、Celina C. Lasota、Benjamin F. Cravatt、Amy R. Howell

  DOI：10.1016/j.bmcl.2014.11.038

  日期：2015.1

  beta-Lactones are a privileged structural motif as enzyme inhibitors and chemical probes, particularly for the inhibition of enzymes from the serine hydrolase class. Herein, we demonstrate that cross-metathesis (CM) of alpha-methylene-beta-lactones offers rapid access to structurally diverse, previously unexplored beta-lactones. Combining this approach with competitive activity-based protein profiling (ABPP) identified lead beta-lactone inhibitors/probes for several serine hydrolases, including disease-associated enzymes and enzymes of uncharacterized function. The structural diversity afforded by the alpha-methylene-beta-lactone scaffold thus expands the landscape of serine hydrolases that can be targeted by small-molecule inhibitors and should further the functional characterization of enzymes from this class through the optimization of target-selective probes. (C) 2014 Elsevier Ltd. All rights reserved.