5-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one | 72719-14-3

• 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: 5-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one
• 英文别名: 5-[(3,4-Dimethoxyphenyl)methyl]oxolan-2-one
• CAS: 72719-14-3
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: VGXGRYVAJOENGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以69%的产率得到5-[(3,4-二羟基苯基)甲基]二氢-2(3H)-呋喃酮
  参考文献：
  名称：

  光学纯形式的儿茶素代谢物 5-(3',4'-二羟基苯基)-γ-戊内酯 (DHPV) 的简明合成及其对皮肤去皱活性的立体化学作用

  摘要：

  通过有效构建 γ- 代谢物，开发了一种简洁且可扩展的光学纯 (4S) 和 (4R)-5-(3',4'-二羟基苯基)-γ-戊内酯 (DHPV) 代谢物合成路线。来自己烯醇的戊内酯部分。值得注意的是，通过我们独特的对映异构纯形式的 DHPV 的合成，揭示了每种代谢物的不同皮肤皱纹减少活性。

  DOI：

  10.3390/molecules25081970
• 作为产物：
  描述：

  (3,4-二甲氧基苯基)乙酰氯 在 乙醚 、 乙醇 、 sodium 作用下， 生成 5-(3,4-dimethoxybenzyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  153.天然酚醛树脂的成分。的一部分X.结构升-matairesinol二甲醚和反应性亚甲基的与缩合观测Ò -methyleugenol氧化物

  摘要：

  DOI：

  10.1039/jr9380000797

文献信息

• Chemo-, Regio- and Stereoselective Heck Arylation of Allylated Malonates: Mechanistic Insights by ESI-MS and Synthetic Application toward 5-Arylmethyl-γ-lactones
  作者：Caio C. Oliveira、Marcelo V. Marques、Marla N. Godoi、Thaís Regiani、Vanessa G. Santos、Emerson A. F. dos Santos、Marcos N. Eberlin、Marcus M. Sá、Carlos R. D. Correia

  DOI：10.1021/ol502529v

  日期：2014.10.3

  We describe herein a general method for the controlled Heck arylation of allylated malonates. Both electron-rich and electron-poor aryldiazonium salts were readily employed as the aryl-transfer agents in good yields and in high chemo-, regio-, and stereoselectivity without formation of decarboxylated byproducts. Reaction monitoring via ESI-MS was used to support the formation of chelated Pd species

  我们在本文中描述了控制烯丙基化丙二酸酯的Heck芳基化的一般方法。富电子和贫电子的芳基重氮盐都容易以高收率和高化学，区域和立体选择性用作芳基转移剂，而不会形成脱羧副产物。通过ESI-MS进行的反应监测用于支持通过催化循环形成螯合的Pd物质。另外，一些Heck加合物已成功用于药理活性γ-内酯的全合成。
• COMPOSITION FOR PREVENTING, IMPROVING OR TREATING PHOTOAGING OF SKIN COMPRISING DHPV
  申请人：SUNGKWANG MEDICAL FOUNDATION

  公开号：US20190021976A1

  公开（公告）日：2019-01-24

  The present invention relates to a photoaging inhibitor, and more specifically it relates to a pharmaceutical composition, a food composition or a cosmetic composition for preventing, improving or treating photoaging of skin, comprising DHPV (5-(3′,4′-Dihydroxyphenyl)-Γ-valerolactone) which is a metabolite of cacao. Since DHPV, an active ingredient comprised in the composition according to the present invention is a metabolite of cacao which is a botanical raw material harmless to human body and is not only excellent in biosafety, but also regulates expression of proteins related to skin aging epigenetically, thereby exhibiting an excellent skin aging-preventing function at a low concentration of 1 nM based on skin cells, the composition comprising the same is excellent in use as medicines, cosmetics and foods for preventing, improving and treating skin aging.

  本发明涉及一种抗光老化剂，更具体地涉及一种用于预防、改善或治疗皮肤光老化的药物组合物、食品组合物或化妆品组合物，包括可可的代谢产物DHPV（5-（3′，4′-二羟基苯基）-Γ-戊内酯）。由于DHPV是本发明中组合物中所含的活性成分，它是可可的代谢产物，可可是一种对人体无害的植物原料，不仅在生物安全性方面表现出色，而且通过表观遗传调节皮肤老化相关的蛋白质的表达，从而在基于皮肤细胞的低浓度1 nM下表现出优异的皮肤抗老化功能，因此，包含相同成分的组合物在预防、改善和治疗皮肤老化方面用作药物、化妆品和食品方面非常出色。
• DHPV의 신규한 합성방법
  申请人：SUNGKWANG MEDICAL FOUNDATION 의료법인 성광의료재단(219950157551) BRN ▼220-82-01517

  公开号：KR102003033B1

  公开（公告）日：2019-07-23

  본 발명은 DHPV의 신규한 합성방법에 관한 것으로, 보다 상세하게는 카카오 주요 대사산물인 DHPV(5-3',4'-Dihydroxyphenyl)-r-valerolactone)의 신규한 합성방법에 관한 것으로, 대량합성이 용이할 뿐만 아니라, 항산화 및 항노화 생리활성을 나타내는 이성질체의 선택이 용이하도록 하다는 장점을 가져, 화장품 및 의약품의 기능성 소재로 높은 가치를 지닐 수 있는 DHPV를 간단하고 경제적으로 대량 생산할 수 있게 한다는 효과를 갖는다.

  这项发明涉及一种新的DHPV合成方法，更详细地说，涉及一种新的合成方法，用于Kakao的主要代谢产物DHPV（5-3'，4'-Dihydroxyphenyl）-r-valerolactone的合成。该方法具有易于大规模合成的优点，使得选择表现出抗氧化和抗衰老生理活性的同分异构体更加容易，从而使DHPV成为具有高价值的功能性化妆品和药物原料，同时实现了简单经济地大规模生产DHPV的效果。
• Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives
  作者：Joshua D. Lambert、Joseph E. Rice、Jungil Hong、Zhe Hou、Chung S. Yang

  DOI：10.1016/j.bmcl.2004.12.070

  日期：2005.2

  Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 muM. (C) 2005 Elsevier Ltd. All rights reserved.
• Watanabe, Journal of the Agricultural Chemical Society of Japan, 1959, vol. 23, p. 257
  作者：Watanabe

  DOI：——

  日期：——