methyl 2-(pent-4-en-1-yloxy)benzoate | 1267478-86-3

• 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: methyl 2-(pent-4-en-1-yloxy)benzoate
• 英文别名: Methyl 2-pent-4-enoxybenzoate
• CAS: 1267478-86-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: IYNOFNISRUNGNI-UHFFFAOYSA-N

物化性质

• 沸点：
  318.9±25.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(pent-4-en-1-yloxy)benzoate 以 甲醇 为溶剂， 反应 4.0h， 以74%的产率得到methyl 2,3,4,4a,5,7a-hexahydrocyclobuta[i]chromene-6-carboxylate
  参考文献：
  名称：

  从O -Pent-4-烯基取代的水杨酸酯到复杂多功能支架的光化学反应级联

  摘要：

  标题化合物的芳烃环被分子内邻位光环加成反应引发的反应级联裂解。通过环辛三烯中间体以高度区域选择性和非对映选择性的方式获得三环产物。系链中立体定位中心施加的面部非对映选择性中等至良好（dr = 65/35至82/18）。产量是可以接受的（44-87％），除了单一基质在系链中具有双甲基双取代作用，并且相应产物的产率仅为14％之外。该反应在烯烃构型（E或Z）方面是立体收敛的，与邻位光环加成步骤的三线态机理相一致。

  DOI：

  10.1021/acs.joc.8b00238
• 作为产物：
  描述：

  5-溴-1-戊烯 、 水杨酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以83%的产率得到methyl 2-(pent-4-en-1-yloxy)benzoate
  参考文献：
  名称：

  研究芳基-二烯双[3 + 2]光环加成反应

  摘要：

  涉及芳基-二烯的双[3 + 2]光环加成反应已用于组装七个单独的[5.5.5.5]芬丝烷结构，其中包括醚和氮杂变体。主要的光解步骤是间位光环加成反应，而次要的光环加成步骤形成芬内酯结构。涉及将额外的亚甲基插入到基本的芳基二烯骨架中的研究未能提供所需的[5.5.5.6]芬太尼结构。芳族光载体中肟部分的存在使主要的光解步骤得以进行。然而，尝试的涉及肟的二次光环加成反应未能提供预期的多杂环芬尼地烯。形成各种“纵横交错”双赢的替代策略对间位光环加合物进行了研究，并发现了丙酮和角间位光环加合物之间的Paterno-Büchi环加成反应。还记录了其他新颖的热和光化学介导的骨骼重排反应。

  DOI：

  10.1021/jo101927a

文献信息

• Exploration of novel macrocyclic dipeptide N-benzyl amides as proteasome inhibitors
  作者：Jianjun Yu、Jieyu Liu、Daqiang Li、Lei Xu、Duidui Hong、Shan Chang、Lei Xu、Jia Li、Tao Liu、Yubo Zhou

  DOI：10.1016/j.ejmech.2018.12.072

  日期：2019.2

  As proteasome inhibitors, a series of novel macrocyclic dipeptide N-benzyl amides were designed, synthesized and evaluated. Most of them exhibited potent proteasome inhibition and excellent anti-proliferative activity against RPMI 8226, MM1S, and MV-4-11 cell lines. As the most distinguished one among this series, compound 23h displayed potent and selective proteasome inhibitory potency (IC50: β5c = 29 nM

  作为蛋白酶体抑制剂，设计，合成和评估了一系列新颖的大环二肽N-苄基酰胺。他们大多数人表现出有效的蛋白酶体抑制作用和对RPMI 8226，MM1S和MV-4-11细胞系的优异抗增殖活性。作为该系列中最杰出的一个，化合物23H显示有效的和选择性的蛋白酶体抑制效力（IC 50：β 5C = 29纳米，β 5I = 35纳米，β 1C，β 2c中， β 1I， β 2I  >10μM），具有IC 50的针对RPMI 8226，MM1S和MV-4-11细胞系的优异抗增殖活性 分别为18 nM，15 nM和21 nM值，以及人肝微粒体（HLM）的良好代谢稳定性，突出表明它是蛋白酶体抑制剂进一步开发的有前途的先导化合物。
• Development of Macrocyclic Peptides Containing Epoxyketone with Oral Availability as Proteasome Inhibitors
  作者：Daqiang Li、Xiaotuan Zhang、Xiaodong Ma、Lei Xu、Jianjun Yu、Lixin Gao、Xiaobei Hu、Jiankang Zhang、Xiaowu Dong、Jia Li、Tao Liu、Yubo Zhou、Yongzhou Hu

  DOI：10.1021/acs.jmedchem.8b00819

  日期：2018.10.25

  Macrocyclization has been frequently utilized for optimizing peptide or peptidomimetic-based compounds. In an attempt to obtain potent, metabolically stable, and orally available proteasome inhibitors, 30 oprozomib-derived macrocyclic peptides with structural diversity in their N-terminus and linker were successively designed and synthesized for structure- activity relationship (SAR) studies. As a consequence, the macrocyclic peptides with N-methyl-pyrazole (24p, 24x), imidazole (24t), and pyrazole (24v) as their respective N-termini exhibited favorable in vitro activity and metabolic stability, which translated into their potent in vivo proteasome inhibitory activity after oral administration. In particular, compound 24v, as the most distinguished one among this series, displayed excellent chymotrypsin-like (ChT-L, beta 5) inhibitory potency (IC50 = 16 nM), low nanomolar antiproliferative activity against all three of the tested cell lines, and superior metabolic stability in mouse liver microsome (MLM), as well as favorable inhibition against ChT-L compared to that of oprozomib in BABL/c mice following po administration at a comparatively low dose, thereby representing a promising candidate for further development.
• CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF
  申请人：Blade Therapeutics, Inc.

  公开号：US20200392157A1

  公开（公告）日：2020-12-17

  Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to macrocyclic α-keto amide derivatives and their use as therapeutic agents.
• Investigating the Arenyl-Diene Double [3 + 2] Photocycloaddition Reaction
  作者：Clive S. Penkett、Jason A. Woolford、Timothy W. Read、Rachel J. Kahan

  DOI：10.1021/jo101927a

  日期：2011.3.4

  The double [3 + 2] photocycloaddition reaction involving arenyl−dienes has been used to assemble seven separate [5.5.5.5] fenestrane structures that include ether and aza variants. The primary photolysis step was a meta photocycloaddition reaction, while a secondary photocycloaddition step formed the fenestrane structure. Investigations involving the insertion of an additional methylene group into

  涉及芳基-二烯的双[3 + 2]光环加成反应已用于组装七个单独的[5.5.5.5]芬丝烷结构，其中包括醚和氮杂变体。主要的光解步骤是间位光环加成反应，而次要的光环加成步骤形成芬内酯结构。涉及将额外的亚甲基插入到基本的芳基二烯骨架中的研究未能提供所需的[5.5.5.6]芬太尼结构。芳族光载体中肟部分的存在使主要的光解步骤得以进行。然而，尝试的涉及肟的二次光环加成反应未能提供预期的多杂环芬尼地烯。形成各种“纵横交错”双赢的替代策略对间位光环加合物进行了研究，并发现了丙酮和角间位光环加合物之间的Paterno-Büchi环加成反应。还记录了其他新颖的热和光化学介导的骨骼重排反应。
• Photochemical Reaction Cascade from <i>O</i>-Pent-4-enyl-Substituted Salicylates to Complex Multifunctional Scaffolds
  作者：Andreas Zech、Thorsten Bach

  DOI：10.1021/acs.joc.8b00238

  日期：2018.3.16

  The arene ring of the title compounds is cleaved by a reaction cascade which is initiated by an intramolecular ortho photocycloaddition reaction. Tricyclic products were obtained in a highly regio- and diastereoselective fashion via a cyclooctatriene intermediate. The facial diastereoselectivity exerted by a stereogenic center in the tether is moderate to good (dr = 65/35 to 82/18). Yields were acceptable

  标题化合物的芳烃环被分子内邻位光环加成反应引发的反应级联裂解。通过环辛三烯中间体以高度区域选择性和非对映选择性的方式获得三环产物。系链中立体定位中心施加的面部非对映选择性中等至良好（dr = 65/35至82/18）。产量是可以接受的（44-87％），除了单一基质在系链中具有双甲基双取代作用，并且相应产物的产率仅为14％之外。该反应在烯烃构型（E或Z）方面是立体收敛的，与邻位光环加成步骤的三线态机理相一致。