4'-O-benzyl-α-hydroxyacetosyringone | 873978-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-O-benzyl-α-hydroxyacetosyringone
• 英文别名: 1-(4-benzyloxy-3,5-dimethoxy-phenyl)-2-hydroxy-ethanone；1-(4-Benzyloxy-3,5-dimethoxy-phenyl)-2-hydroxy-aethanon；1-(3,5-Dimethoxy-4-phenylmethoxyphenyl)-2-hydroxyethanone
• CAS: 873978-83-7
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: NCOQZCYVECMLLT-UHFFFAOYSA-N

物化性质

• 沸点：
  460.8±40.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-O-benzyl-α-hydroxyacetosyringone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以95%的产率得到3',5'-二甲氧基-4'-羟基-(2-羟基)苯乙酮
  参考文献：
  名称：

  Synthesis of α-Hydroxyacetosyringone

  摘要：

  从木瓜果实中提取的一种植物皂苷经四个步骤合成；这一过程涉及一种普默尔（Pummerer）型反应。

  DOI：

  10.3390/51201287
• 作为产物：
  描述：

  3',5'-dimethoxy-4'-benzyloxyphenylethenylmethylsulfoxide 在 盐酸 作用下， 反应 5.0h， 以10%的产率得到4'-O-benzyl-α-hydroxyacetosyringone
  参考文献：
  名称：

  Synthesis of α-Hydroxyacetosyringone

  摘要：

  从木瓜果实中提取的一种植物皂苷经四个步骤合成；这一过程涉及一种普默尔（Pummerer）型反应。

  DOI：

  10.3390/51201287

文献信息

• NOVEL BENZAMIDE DERIVATIVE AND USE THEREOF
  申请人：VIVOZON, INC.

  公开号：US20140336378A1

  公开（公告）日：2014-11-13

  Disclosed are a novel benzamide derivative and pharmaceutical use thereof, and more particularly, a novel benzamide derivative having a structure of Formula 1 or pharmaceutically acceptable salts thereof, and a composition for prevention or treatment of pain or itching including the above material. The novel benzamide derivative and pharmaceutically acceptable salt thereof according to the present invention exhibit excellent pain-suppressive effect and, in particular, pain-suppressive effect in not only a neuropathic animal model but also other models such as a formalin model, and therefore, may be used in suppression of different pains such as nociceptive pain, chronic pain, etc. Further, since it was demonstrated that the present invention displays anti-pruritic efficacy even in an itching model, to which a mechanism and treatment concept established with respect to pain is applied, the present invention may also be effectively used in radical treatment of atopic dermatitis by applying the inventive product to an anti-pruritic composition in order to suppress an initial itching stage and treat symptoms thereof, thus preventing skin damage or inflammation after the scratching stage.

  揭示了一种新的苯甲酰胺衍生物及其药用，更具体地说，一种具有化学式1结构或其药用盐的新苯甲酰胺衍生物，以及包括上述材料的用于预防或治疗疼痛或瘙痒的组合物。根据本发明，所述新的苯甲酰胺衍生物及其药用盐表现出优异的镇痛效果，特别是在不仅神经病理动物模型中而且其他模型如福尔马林模型中表现出的镇痛效果，因此，可用于抑制不同类型的疼痛，如伤害性疼痛、慢性疼痛等。此外，由于证明了本发明在瘙痒模型中显示出抗瘙痒功效，应用于疼痛方面建立的机制和治疗概念，因此，本发明还可通过将创新产品应用于抗瘙痒组合物中，以抑制初始瘙痒阶段并治疗其症状，从而预防刮痒阶段后的皮肤损伤或炎症。
• CsPbBr₃ Quantum Dots Promoted Depolymerization of Oxidized Lignin via Photocatalytic Semi‐Hydrogenation/Reduction Strategy
  作者：Huating Jiang、Minxia Liu、Xiao Lian、Mingxiang Zhu、Fang Zhang

  DOI：10.1002/anie.202318850

  日期：2024.2.12

  Due to the demanding depolymerization conditions and limited catalytic efficiency, enhancing lignin valorization remains challenging. Therefore, lowering the bond dissociation energy (BDE) has emerged as a viable strategy for achieving mild yet highly effective cleavage of bonds. In this study, a photocatalytic semi‐hydrogenation/reduction strategy utilizing CsPbBr₃ quantum dots (CPB‐QDs) and Hantzsch ester (HEH₂) as a synergistic catalytic system was introduced to reduce the BDE of C_β−O−Ar, achieving effective cleavage of the C_β−O−Ar bond. This strategy offers a wide substrate scope encompassing various β‐O‐4 model lignin dimers, preoxidized β‐O‐4 polymers, and native oxidized lignin, resulting in the production of corresponding ketones and phenols. Notably, this approach attained a turnover frequency (TOF) that is 17 times higher than that of the reported Ir‐catalytic system in the photocatalytic depolymerization of the lignin model dimers. It has been observed via meticulous experimentation that HEH₂ can be activated by CPB‐QDs via single electron transfer (SET), generating HEH₂⋅⁺ as a hydrogen donor while also serving as a hole quencher. Moreover, HEH₂⋅⁺ readily forms an active transition state with the substrates via hydrogen bonding. Subsequently, the proton‐coupled electron transfer (PCET) from HEH₂⋅⁺ to the carbonyl group of the substrate generates a C_α⋅ intermediate.

  摘要由于苛刻的解聚条件和有限的催化效率，提高木质素的价值仍具有挑战性。因此，降低键解离能（BDE）已成为实现温和而高效的键裂解的可行策略。本研究采用了一种光催化半氢化/还原策略，利用 CsPbBr3 量子点（CPB-QDs）和汉茨酯（HEH2）作为协同催化系统，降低 Cβ-O-Ar 的 BDE，从而实现 Cβ-O-Ar 键的有效裂解。这种策略提供了广泛的底物范围，包括各种 β-O-4 模型木质素二聚体、预氧化的 β-O-4 聚合物和原生氧化木质素，从而产生相应的酮和酚。值得注意的是，在木质素模型二聚体的光催化解聚过程中，这种方法达到的周转频率（TOF）是已报道的铱催化系统的 17 倍。通过细致的实验观察发现，CPB-QDs 可通过单电子转移（SET）激活 HEH2，生成 HEH2⋅+ 作为氢供体，同时还可作为空穴淬灭剂。此外，HEH2⋅+ 很容易通过氢键与底物形成活性过渡态。随后，质子耦合电子转移（PCET）从 HEH2⋅+ 到底物的羰基，生成 Cα⋅ 中间体。
• Bradley; Robinson, Journal of the Chemical Society, 1928, p. 1551
  作者：Bradley、Robinson

  DOI：——

  日期：——
• US9359346B2
  申请人：——

  公开号：US9359346B2

  公开（公告）日：2016-06-07