4-(2'-methoxycarbonylphenoxy)but-1-ene | 141946-22-7

• 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: 4-(2'-methoxycarbonylphenoxy)but-1-ene
• 英文别名: methyl 2-(but-3-en-1-yloxy)benzoate；2-But-3-enyloxy-benzoic acid methyl ester；methyl 2-but-3-enoxybenzoate
• CAS: 141946-22-7
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: AAPRROXMSXXYRR-UHFFFAOYSA-N

物化性质

• 沸点：
  297.8±23.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-(2'-methoxycarbonylphenoxy)but-1-ene 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 benzyl O-allyl-N-(N-(2-(but-3-en-1-yloxy)benzoyl)-O-methyl-L-seryl)-L-serinate
  参考文献：
  名称：

  Development of Macrocyclic Peptides Containing Epoxyketone with Oral Availability as Proteasome Inhibitors

  摘要：

  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.

  DOI：

  10.1021/acs.jmedchem.8b00819
• 作为产物：
  描述：

  4-溴-1-丁烯 、 水杨酸甲酯 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 生成 4-(2'-methoxycarbonylphenoxy)but-1-ene
  参考文献：
  名称：

  4-苯氧基丁-1-烯的分子内光环加成：方便地获得4-氧杂三环[7.2.0.0] undeca-2,10-二烯骨架

  摘要：

  4-苯氧基丁-1-烯的光化学显着地受到苯环上吸电子取代基的存在和位置的影响。2'-或4'-位的氰基取代基通过光不稳定的11-氧杂双环[]促进分子内有效的环加成反应，从而产生4-氧杂三环-[7.2.0.0] undeca-2,10-二烯的良好收率。 6.3.0] undeca-1,3,5-三烯，其前体被认为是热不稳定的分子内邻位光环加合物。3'-氰基异构体反应不充分，只有甲氧基羰基系列中的2'-异构体发生光环加成。三烯的形成可被1,3-二烯有效地淬灭，但它们的分子内环化不受三线态淬灭剂的影响。

  DOI：

  10.1039/p19920001145

文献信息

• 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。
• Construction of medium-ring oxacycloalkenones. Extension towards benzo-fused cyclic ethers
  作者：Frédéric Lecornué、Jean Ollivier

  DOI：10.1039/b307289b

  日期：——

  Application of the intramolecular Kulinkovich cyclopropanation of oxa-ω-alkenoic esters followed by Saegusa oxidation and dehydrohalogenation led to simple or benzo-fused oxacycloalkenones, basic structural elements in a wide range of naturally occurring compounds.

  应用氧杂-ω-烯酸酯的分子内库林科维奇环丙烷化，然后进行 Saegusa 氧化和脱卤化氢，产生了简单或苯并稠合的氧杂环烯酮，这是多种天然化合物中的基本结构元素。
• Intramolecular photochemical reactivity of O-alk-3-enylsalicylic esters
  作者：Norbert Hoffmann、Jean-Pierre Pete

  DOI：10.1016/0040-4039(95)00352-d

  日期：1995.4

  Irradiation of O-alk-3-enylsalycylates 1 at lambda = 254 nm yields tricyclic compounds 2 containing a cyclobutene moiety. The efficiency of the intramolecular photocycloaddition increased and the reaction mixture was greatly simplified when the reaction was carried out in methanol in the presence of a catalytic amount of acid.
• Hoffmann Norbert, Pete Jean-Pierre, Tetrahedron Lett, 36 (1995) N 15, S 2623-2626
  作者：Hoffmann Norbert, Pete Jean-Pierre

  DOI：——

  日期：——