(E)-4-苯基-2-丁烯酸 | 2243-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (E)-4-苯基-2-丁烯酸
• 英文名称: 3-benzylacrylic acid
• 英文别名: 4-phenylbut-2-enoic acid；4-Phenyl-crotonsaeure；4-Phenylbutenoesaeure；γ-Phenylcrotonsaeure；4-phenyl-crotonic acid
• CAS: 2243-52-9
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: SCBUQIQXUBOQAI-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  137-138 °C(Press: 2 Torr)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (E)-4-苯基-2-丁烯酸 在 吡啶 作用下， 生成 4-苯基-3-丁烯酸
  参考文献：
  名称：

  Bougault, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1917, vol. 164, p. 635

  摘要：

  DOI：
• 作为产物：
  描述：

  4-苯基-3-丁烯酸 生成 (E)-4-苯基-2-丁烯酸
  参考文献：
  名称：

  Linstead; Williams, Journal of the Chemical Society, 1926, p. 2745

  摘要：

  DOI：

文献信息

• Synthesis of cyanofuroxans from 4-nitrofuroxans via C C bond forming reactions
  作者：Ryosuke Matsubara、Akihiro Ando、Masahiko Hayashi

  DOI：10.1016/j.tetlet.2017.07.015

  日期：2017.8

  direct synthesis process. The optimized reaction conditions showed an excellent applicability for the synthesis of a range of 4-cyanofuroxans. 3-Cyanofuroxans, known to be thiol-mediated nitric oxide donors, could also be obtained by the thermal or photochemical isomerization of 4-cyanofuroxans. The developed cyanation of furoxans is a rare example of CC bond-forming reaction on a furoxan ring.

  描述了4-硝基呋喃烷的取代反应以制备4-氰基呋喃烷。逆反应使该取代反应复杂化，明智地选择氰化物源对于实现这种直接合成过程很重要。优化的反应条件显示出极好的适用于合成一系列4-氰基呋喃聚糖。3-氰基呋喃类，已知是硫醇介导的一氧化氮供体，也可以通过4-氰基呋喃类的热或光化学异构化获得。呋喃喃的发达氰化反应是呋喃环上形成C C键的罕见反应。
• The studies on the chemoenzymatic synthesis of 2-benzyl-3-butenoic acid
  作者：Filip Borys、Daniel Paprocki、Dominik Koszelewski、Ryszard Ostaszewski

  DOI：10.1016/j.catcom.2018.05.020

  日期：2018.8

  The studies on the chemoenzymatic synthesis of 2-benzyl-3-butenoic acid 3 were performed. The alkylation of dienolates derived from the crotonic and vinylacetic acids with different types of alkylating agents was examined. In all cases the inseparable mixture of isomeric acids 3 and 4 were obtained. Chemoselective enzymatic esterification of those mixtures provides ester 6 in 86% yield as a single

  化学合成2-苄基-3-丁烯酸3的研究。检查了来自巴豆酸和乙烯基乙酸的二烯酸酯与不同类型的烷基化剂的烷基化。在所有情况下，均获得了异构体3和4的不可分离的混合物。这些混合物的化学选择性酶促酯化以单一产物形式提供酯6，收率为86％，而没有双键异构化。没有一种通用的方法可用于其水解，因为在碱性条件下仅形成异构酸5。为了克服该限制，设计了酶催化的水解过程。该方案以98％的产率提供了异​​构纯的酸3。
• Selective oxidation of aromatic primary alcohols to aldehydes using molybdenum acetylide oxo-peroxo complex as catalyst
  作者：Ankush V. Biradar、Mohan K. Dongare、Shubhangi B. Umbarkar

  DOI：10.1016/j.tetlet.2009.03.178

  日期：2009.6

  Selective oxidation of various aromatic alcohols to aldehydes has been carried out with very high conversion (90%) and selectivity (90%) for aldehydes using cyclopentadienyl molybdenum acetylide complex, CpMo(CO)3(CCPh) (1) as catalyst and hydrogen peroxide as environmentally benign oxidant. Water-soluble Mo acetylide oxo-peroxo species is formed in situ after reaction of 1 with aqueous hydrogen peroxide

  使用环戊二烯基乙炔钼络合物，CPMo（CO）3（C CPh）（1）作为催化剂和氢气，已以很高的转化率（90％）和对醛的选择性（90％）进行了各种芳香醇选择性氧化为醛的反应。过氧化物作为对环境无害的氧化剂。1的反应后在原位形成水溶性的乙炔酸钼氧-过氧物质在反应过程中用过氧化氢水溶液作为催化活性物质。有趣的是，即使催化剂是均相的，通过使用分液漏斗分离有机相中的产物和水相中的催化剂，也可以非常容易地将其再循环。即使经过五次循环，也没有观察到明显的醇转化率和醛选择性损失。
• Knoevenagel-Doebner condensation promoted by chitosan as a reusable solid base catalyst
  作者：Nagaraj Anbu、Surendran Hariharan、Amarajothi Dhakshinamoorthy

  DOI：10.1016/j.mcat.2019.110744

  日期：2020.3

  although Knoevenagel-Doebner condensation reaction has been reported with many organocatalysts including proline, no attempts were made to develop heterogeneous catalysts with environmental concerns. Considering these factors in mind, the title reaction is studied with chitosan as a heterogeneous solid base catalyst for the synthesis of α,β-unsaturated carboxylic acids through the condensation followed

  使用天然存在的生物聚合物开发绿色和可持续性工艺正成为替代传统催化系统的合适方法之一，传统催化系统会产生大量具有高风险因素的副产物。在这种情况下，尽管已经报道了Knoevenagel-Doebner与包括脯氨酸在内的许多有机催化剂的缩合反应，但未尝试开发涉及环境问题的多相催化剂。考虑到这些因素，以壳聚糖为多相固体碱催化剂研究了标题反应，该反应通过缩合然后脱羧反应合成α，β-不饱和羧酸。壳聚糖具有许多优势，例如浸出，可重复使用性测试，广泛的底物范围，并以更高的纯度提供所需产品的更高产量。粉末X射线衍射（XRD），傅立叶变换红外光谱（FT-IR），扫描电子显微镜（SEM）和元素分析表明，在优化反应条件下，催化前后壳聚糖的结构完整性和形态没有重大变化。情况。
• Substituted (aryl, heteroaryl, arylmethyl or heteroarylmethyl)
  申请人：Rhone-Poulenc Rorer Pharmaceuticals Inc.

  公开号：US06057369A1

  公开（公告）日：2000-05-02

  This invention is directed to compounds of formula I: ##STR1## wherein the variables are as described herein. Compounds within the scope of the present invention possess useful properties, more particularly pharmaceutical properties. They are especially useful for inhibiting the production or physiological effects of TNF in the treatment of a patient suffering from a disease state associated with a physiologically detrimental excess of tumor necrosis factor (TNF). Compounds within the scope of the present invention also inhibit cyclic AMP phosphodiesterase, and are useful in treating a disease state associated with pathological conditions that are modulated by inhibiting cyclic AMP phosphodiesterase, such disease states including inflammatory and autoimmune diseases, in particular type IV cyclic AMP phosphodiesterase. Compounds within the scope of the present invention may also inhibit an MMP, and are useful in treating a disease state associated with pathological conditions that are modulated by inhibiting MMPs, such disease states involve tissue breakdown and those associated with a physiologically detrimental excess of TNF. The present invention is therefore also directed to the pharmaceutical use of the compounds, pharmaceutical compositions containing the compounds, intermediates leading thereto and methods for the preparation of the compounds and their intermediates.

  本发明涉及式I的化合物：##STR1## 其中变量如本文所述。本发明所涵盖的化合物具有有用的性质，特别是药物性质。它们在治疗患有与生理有害的肿瘤坏死因子（TNF）过度相关的疾病状态的患者中抑制TNF的产生或生理效应特别有用。本发明所涵盖的化合物还抑制环磷酸腺苷磷酸二酯酶，并且在治疗与抑制环磷酸腺苷磷酸二酯酶有关的病理条件的疾病状态中有用，这些疾病状态包括炎症和自身免疫性疾病，特别是第四型环磷酸腺苷磷酸二酯酶。本发明所涵盖的化合物还可能抑制MMP，并且在治疗与抑制MMP有关的病理条件的疾病状态中有用，这些疾病状态涉及组织分解和与TNF过度有害相关的疾病状态。因此，本发明还涉及化合物的药物用途、含有该化合物的药物组合物、导致其中间体的中间体以及制备该化合物及其中间体的方法。