3-methylene-4-tridecyloxetan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-methylene-4-tridecyloxetan-2-one
• 英文别名: 3-Methylene-4-tridecyloxetan-2-one；3-methylidene-4-tridecyloxetan-2-one
• 化学式: C₁₇H₃₀O₂
• 分子量: 266.424
• InChiKey: PFZSCBZBKIRZKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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-methylene-4-tridecyloxetan-2-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium tetrahydroborate 、 双(三苯基膦)氯化钴 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 10.17h， 生成 cis-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
• 作为产物：
  描述：

  肉豆蔻醛 在 三乙烯二胺 、 mercury(II) trifluoroacetate 作用下， 以 乙腈 为溶剂， 反应 168.17h， 生成 3-methylene-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

• Rh-Catalyzed Conjugate Addition of Aryl and Alkenyl Boronic Acids to α-Methylene-β-lactones: Stereoselective Synthesis of <i>trans</i>-3,4-Disubstituted β-Lactones
  作者：Christian A. Malapit、Irungu K. Luvaga、Donald R. Caldwell、Nicholas K. Schipper、Amy R. Howell

  DOI：10.1021/acs.orglett.7b01994

  日期：2017.9.1

  A one-step preparation of 3,4-disubstituted β-lactones through Rh-catalyzed conjugate addition of aryl or alkenyl boronic acids to α-methylene-β-lactones is described. The operationally simple, stereoselective transformation provides a broad range of β-lactones from individual α-methylene-β-lactone templates. This methodology allowed for a direct, final-step C-3 diversification of nocardiolactone,

  描述了一种通过Rh催化的芳基或烯基硼酸到α-亚甲基-β-内酯的共轭加成反应，一步一步制备3,4-二取代的β-内酯的方法。操作简单，立体选择性转化可从各个α-亚甲基-β-内酯模板中提供广泛的β-内酯。这种方法可以使诺卡固内酯（一种抗菌天然产品）直接进行最后的C-3多元化生产。
• 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.
• Pd-Catalyzed Acyl C–O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines
  作者：Christian A. Malapit、Donald R. Caldwell、Nicole Sassu、Samuel Milbin、Amy R. Howell

  DOI：10.1021/acs.orglett.7b00494

  日期：2017.4.21

  A Pd-catalyzed ring-opening of beta-lactones with various types of amines (primary, secondary, and aryl) to provide beta-hydroxy amides with excellent selectivity toward acyl C-O bond cleavage is reported. The utility of this protocol is demonstrated in an asymmetric kinetic resolution providing enantioenriched a-methylene-beta-lactones.
• 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.