3-(2-naphthyl)-3-butenoic acid | 941293-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(2-naphthyl)-3-butenoic acid
• 英文别名: 3-(2-naphthyl)but-3-enoic acid；3-Naphthalen-2-ylbut-3-enoic acid；3-naphthalen-2-ylbut-3-enoic acid
• CAS: 941293-40-9
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: FYELSYQSBWQDRW-UHFFFAOYSA-N

物化性质

• 沸点：
  408.0±14.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-naphthyl)-3-butenoic acid 在 [Rh(S_P,R_C)-DuanPhos(nbd)]SbF₆ 氢气 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、303.99 kPa 条件下， 反应 12.0h， 以97%的产率得到(S)-3-(naphthalen-2-yl)butanoic acid
  参考文献：
  名称：

  Rh催化的3-芳基丁酸的高度对映选择性合成。

  摘要：

  DOI：

  10.1002/anie.200604810
• 作为产物：
  描述：

  双乙烯酮 、 2-溴萘 在 四(三苯基膦)钯 magnesium 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-(2-naphthyl)-3-butenoic acid
  参考文献：
  名称：

  Rh催化的3-芳基丁酸的高度对映选择性合成。

  摘要：

  DOI：

  10.1002/anie.200604810

文献信息

• Hypervalent Iodine(III)-Mediated Oxidative Decarboxylation of β,γ-Unsaturated Carboxylic Acids
  作者：Kensuke Kiyokawa、Shunsuke Yahata、Takumi Kojima、Satoshi Minakata

  DOI：10.1021/ol5022433

  日期：2014.9.5

  acids mediated by hypervalent iodine(III) reagents is described. The decarboxylative C–O bond forming reaction proceeded in the presence of PhI(OAc)2 to give the corresponding allylic acetates. In addition, decarboxylative C–N bond formation was achieved by utilizing hypervalent iodine(III) reagents containing an I–N bond. Mechanistic studies suggest the unique reactivity of hypervalent iodine reagents

  描述了一种由高价碘（III）试剂介导的新型β，γ-不饱和羧酸的氧化脱羧反应。在PhI（OAc）2的存在下进行脱羧C-O键形成反应，得到相应的烯丙基乙酸酯。此外，通过使用含有I–N键的高价碘（III）试剂可实现脱羧C–N键的形成。机理研究表明，高价碘试剂在这种离子氧化脱羧反应中具有独特的反应性。
• Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones
  作者：Kensuke Kiyokawa、Satoshi Minakata、Kenta Takemoto、Shunsuke Yahata、Takumi Kojima

  DOI：10.1055/s-0036-1588987

  日期：2017.7

  Published as part of the Special Topic Modern Strategies with Iodine in Synthesis� Abstract The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf)2, which is in situ prepared from PhI(OAc)2 and Me3SiOTf, is crucial. Depending

  作为合成中碘的现代战略特别主题的一部分出版。 抽象的 报道了使用高价碘试剂对β-取代的β，γ-不饱和羧酸进行氧化环化，以提供4-取代的呋喃-2-酮产物。在这种环化中，至关重要的是使用由PhI（OAc）2和Me 3 SiOTf原位制备的高度亲电的PhI（OTf）2。根据底物在α位的取代方式，产生呋喃-2（5 H）-一个或呋喃-2（3 H）-一个。因此，本方法提供了一种有用的工具，用于获得各种类型的4-取代的呋喃-2-酮，所述4-取代的呋喃-2-酮是有机化学和药物化学领域中的重要结构基序。 报道了使用高价碘试剂对β-取代的β，γ-不饱和羧酸进行氧化环化，以提供4-取代的呋喃-2-酮产物。在这种环化中，至关重要的是使用由PhI（OAc）2和Me 3 SiOTf原位制备的高度亲电的PhI（OTf）2。根据底物在α位的取代方式，产生呋喃-2（5 H）-一个或呋喃-2（3 H）-一个。因此，本方法提供
• Enantioselective direct vinylogous aldol-cyclization cascade reaction between β,γ-unsaturated amides and o-quinones
  作者：Yu Jiang、Jun-Hao Fu、Tian-Ze Li、Feng Sha、Xin-Yan Wu

  DOI：10.1039/c6ob00893c

  日期：——

  1,2-Diketones are employed, for the first time, as electrophiles in the vinylogous aldol reaction. With 5 mol% of chiral tertiary amine-thiourea C8, a direct vinylogous aldol-cyclization cascade reaction between β,γ-unsaturated amides and o-quinones has been achieved to produce spirocyclic dihydropyranones in 76–99% yield and 82–95% ee.

  1,2-二酮首次用作乙烯基醇醛醇醛反应中的亲电子试剂。使用5 mol％的手性叔胺硫脲C8，可以实现β，γ-不饱和酰胺与邻醌之间的直接乙烯基醛醇缩合级联反应，以76-99％的收率和82-95％ee的产率生产螺环二氢吡喃酮。 。
• Hydroxamic acid inhibitors of 5-lipoxygenase: quantitative structure-activity relationships
  作者：James B. Summers、Ki H. Kim、Hormoz Mazdiyasni、James H. Holms、James D. Ratajczyk、Andrew O. Stewart、Richard D. Dyer、George W. Carter

  DOI：10.1021/jm00165a017

  日期：1990.3

  An evaluation of the quantitative structure-activity relationships (QSAR) for more than 100 hydroxamic acids revealed that the primary physicochemical feature influencing the in vitro 5-lipoxygenase inhibitory potencies of these compounds is the hydrophobicity of the molecule. A significant correlation was observed between the octanol-water partition coefficient of the substituent attached to the carbonyl of the hydroxamate and in vitro inhibitory activity. This correlation held for hydroxamic acids of diverse structure and with potencies spanning 4 orders of magnitude. Although the hydrophobicity may be packaged in a variety of structural ways and still correlate with potency, the QSAR study revealed two major exceptions. Specifically, the hydrophobicity of portions of compounds in the immediate vicinity of the hydroxamic acid functionality does not appear to contribute to increased inhibition and the hydrophobicity of fragments beyond approximately 12 A from the hydroxamate do not influence potency. The QSAR study also demonstrated that inhibitory activity was enhanced when there was an alkyl group on the hydroxamate nitrogen, when electron-withdrawing substituents were present and when the hydroxamate was conjugated to an aromatic system. These observations provide a simple description of the lipoxygenase-hydroxamic acid binding site.
• Rh-Catalyzed Highly Enantioselective Synthesis of 3-Arylbutanoic Acids
  作者：Xianfeng Sun、Le Zhou、Chun-Jiang Wang、Xumu Zhang

  DOI：10.1002/anie.200604810

  日期：2007.4.2