3,5-dimethoxy-4-benzyloxycinnamic acid | 14897-77-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3,5-dimethoxy-4-benzyloxycinnamic acid
• 英文别名: 4-O-benzylsinapic acid；4-Benzyloxy-3,5-dimethoxy-zimtsaeure；3-(3,5-dimethoxy-4-phenylmethoxyphenyl)prop-2-enoic acid
• CAS: 14897-77-9
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: IJRFQQCIUDWZLT-UHFFFAOYSA-N

物化性质

• 沸点：
  495.2±40.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  3,5-dimethoxy-4-benzyloxycinnamic acid 、 (2R/S)-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]carbinol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.0h， 以80%的产率得到(6'-benzyloxy-2',5',7',8'-tetramethylchroman-2'-yl)methyl 3,5-dimethoxy-4-benzyloxycinnamate
  参考文献：
  名称：

  储存和油炸过程中油类的自由基清除活性和新型酚类抗氧化剂的性能

  摘要：

  AbstractNovel phenolic antioxidants: 2a (6′‐hydroxy‐2′,5′,7′,8′‐tetramethylchroman‐2′‐yl)methyl 3‐methoxy‐4‐hydroxycinnamate, 2b (6′‐hydroxy‐2′,5′,7′,8′‐tetramethylchroman‐2′‐yl)methyl 3,5‐dimethoxy‐4‐hydroxycinnamate, 2c (6′‐hydroxy‐2′,5′,7′,8′‐tetramethylchroman‐2′‐yl)methyl 3,4‐dihydroxycinnamate, and 3 (6‐hydroxy‐2,5,7,8‐tetramethylchroman‐2‐yl)methyl (6′‐hydroxy‐2′,5′,7′,8′‐tetramethylchroman‐2′‐carboxylate) have been prepared in good yields and fully characterized by 1H and 13C NMR, and HRMS. Their radical scavenging activities have been evaluated by DPPH and ORAC assays. Each of the synthesized antioxidants exhibited significantly higher radical scavenging activities than trolox and α‐tocopherol. These novel antioxidants efficiently protected canola oil triacylglycerides (CTG) during accelerated storage and frying. Compounds 2c and 3 were significantly more efficient than α‐tocopherol protecting CTG under accelerated storage. All new antioxidants were more efficient than α‐tocopherol under frying conditions and present significantly higher thermal stability.

  DOI：

  10.1007/s11746-011-1889-6
• 作为产物：
  描述：

  丁香醛 在 氢氧化钾 、 potassium carbonate 作用下， 以 乙醇 、 水 、 丙酮 、 苯 为溶剂， 反应 3.0h， 生成 3,5-dimethoxy-4-benzyloxycinnamic acid
  参考文献：
  名称：

  Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives

  摘要：

  Five series totalling 51 of sinapyl alcohol derivatives were designed and synthesized. Their cytotoxicity analyses were performed oil six human tumor cell lines Such as PC-3. CNE, KB, A549, BEL-7404, and HeLa. Certain sinapyl alcohol derivatives showed significant cytotoxic activities. Compound 14d exhibited especially potent cytotoxicity against the BEL-7404 cell line with an IC50 value of 0.7 mu M, which showed more cytotoxic activity than the positive control, cisplatin. The structure-cytotoxicity relationships were discussed and the CoMFA analysis was performed using the cytotoxic data against HeLa cells as a template. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.056

文献信息

• METHOD FOR PREPARING FUROFURAN LIGNAN COMPOUND
  申请人：Cho Si Young

  公开号：US20150073158A1

  公开（公告）日：2015-03-12

  The present invention relates to a method for preparing a furofuran lignan compound, comprising a step of selecting and alkylating an epoxy alcohol compound and an optical isomer thereof. (+)-furofuran lignan and (−)-furofuran lignan, as well as an optical isomer thereof, can be selectively prepared by means of the method.

  本发明涉及一种用于制备呋喃木质素化合物的方法，包括选择和烷基化环氧醇化合物及其光学异构体的步骤。通过该方法可以选择性地制备（+）-呋喃木质素和（-）-呋喃木质素，以及它们的光学异构体。
• ANTI-HIV COMPOUNDS
  申请人：Prosetta Antiviral, Inc.

  公开号：US20160168100A1

  公开（公告）日：2016-06-16

  This invention provides, among other things, tetrahydroisoquinolines useful for treating viral infections, pharmaceutical formulations containing such compounds, as well as methods of inhibiting the replication of a virus, such as HIV, or treating a disease, such as AIDS.

  这项发明提供了用于治疗病毒感染的四氢异喹啉等化合物，含有这类化合物的药物配方，以及抑制病毒（如HIV）复制或治疗疾病（如艾滋病）的方法。
• Therapeutic agents for use in the treatment of parkinson's disease
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0565377A1

  公开（公告）日：1993-10-13

  Disclosed are therapeutic agents for use in the treatment of Parkinson's disease, such agents being xanthine derivatives of the Formula (I) and their pharmaceutical acceptable salts : where R1, R2 and R3 are each H, C1-C6 alkyl or allyl ; and R4 is cycloalkyl of 3 to 8 carbon atoms, a -(CH2)n-R5 group where n is an cycloalkyl of 3 to 8 carbon atoms, a - (CH2)n-R5 group where n is an integer of from 0-4 and R5 is an aryl group of 6 to 10 carbon atoms or a heterocyclic group, such aryl or heterocyclic group optionally being substituted by up to 3 substituent(s) selected from C1-C6 alkyl, hydroxy, C1-C6 alkoxy, halogen, nitro and amino ; or a group, where Y1 and Y2 are each H or CH3 and Z is a substituted or unsubstituted aryl or heterocyclic group as defined under R5.

  本发明揭示了治疗帕金森病的治疗剂，该治疗剂为公式（I）的黄嘌呤衍生物及其药物可接受的盐：其中，R1、R2和R3分别为H、C1-C6烷基或丙烯基；而R4为3至8个碳原子的环烷基，-(CH2)n-R5基团，其中n为3至8个碳原子的环烷基，-(CH2)n-R5基团，其中n为0-4的整数，而R5为6至10个碳原子的芳基基团或杂环基团，所述芳基或杂环基团可选地被选自C1-C6烷基，羟基，C1-C6烷氧基，卤素，硝基和氨基的最多3个取代基所取代；或Y1和Y2分别为H或CH3，而Z为根据R5所定义的取代或未取代的芳基或杂环基团的一个基团。
• ANTIDEPRESSANT
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0628311A1

  公开（公告）日：1994-12-14

  An antidepressant containing an active ingredient comprising a xanthine derivative represented by general formule (I) or a pharmacologically acceptable salt thereof, wherein R¹, R² and R³ may be the same or different from one another and each represents hydrogen, lower alkyl, alkyl or propargyl; R⁴ represents cycloalkyl, -(CH₂)n-R⁵ (wherein R⁵ represents optionally substituted aryl or optionally substituted heterocyclic group, and n represents an integer of 0 to 4) of group (A) wherein Y¹ and Y² may be the same or different from each other and each represents hydrogen, fluorine or methyl, and Z represents optionally substituted aryl, group (B) (wherein R⁶ represents hydrogen, hydroxy, lower alkyl, lower alkoxy, halogen, nitro or amino, and m represents an integer of 1 to 3), or optionally substituted heterocyclic group; and X¹ and X² may be the same or different from each other and each represents O or S.

  一种含有活性成分的抗抑郁剂，其活性成分包含通式(I)所代表的黄嘌呤衍生物或其药理上可接受的盐，其中 R¹、R² 和 R³ 可以相同或彼此不同，且各自代表氢、低级烷基、烷基或丙炔基；R⁴ 代表(A)基团的环烷基、-(CH₂)n-R⁵（其中 R⁵ 代表任选取代的芳基或任选取代的杂环基团，且 n 代表 0 至 4 的整数），其中 Y¹ 和 Y² 可以相同或不同，且各自代表氢、氟或甲基，Z 代表任选取代的芳基、基团 (B)（其中 R⁶ 代表氢、羟基、低级烷基、低级烷氧基、卤素、硝基或氨基，m 代表 1 至 3 的整数）或任选取代的杂环基团；X¹ 和 X² 可以相同或不同，各自代表 O 或 S。
• 2-phenethenyltetrahydro isoquinolines useful as anti-HIV compounds
  申请人：Prosetta Antiviral, Inc.

  公开号：US10195189B2

  公开（公告）日：2019-02-05

  This invention provides, among other things, tetrahydroisoquinolines useful for treating viral infections, pharmaceutical formulations containing such compounds, as well as methods of inhibiting the replication of a virus, such as HIV, or treating a disease, such as AIDS.

  除其他外，本发明还提供了用于治疗病毒感染的四氢异喹啉类化合物、含有此类化合物的药物制剂，以及抑制艾滋病毒等病毒复制或治疗艾滋病等疾病的方法。