β-(2-Hydroxy-4-methoxy-phenyl)-propionsaeure | 21144-17-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: β-(2-Hydroxy-4-methoxy-phenyl)-propionsaeure
• 英文别名: 3-(2'-hydroxy-4'-methoxyphenyl)propanoic acid；3-(2-Hydroxy-4-methoxyphenyl)propanoic acid
• CAS: 21144-17-2
• 化学式: C₁₀H₁₂O₄
• mdl: MFCD00220591
• 分子量: 196.203
• InChiKey: CGWRDLSMEFSEDN-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C
• 沸点：
  388.0±27.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-(2-Hydroxy-4-methoxy-phenyl)-propionsaeure 在 sodium hydroxide 、 氯化亚砜 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 为溶剂， 反应 115.0h， 生成 3-(2'-benzyloxy-4'-methoxyphenyl)-N-methyl-N-phenylpropanamide
  参考文献：
  名称：

  Conversion of 7-methoxy-3,4-dihydro-2H-1-benzopyran-2-one into the corresponding dimethyl ortho ester

  摘要：

  7-Methoxy-3,4-dihydro-2H-1-benzopyran-2-one 2 was converted into 3-(2'-tert-butyldimethylsilyloxy-4'-methoxyphenyl)-N-Methyl-N-phenylpropanamide 25 and reaction of this with methyl trifluoromethanesulfonate, followed by reaction with sodium methoxide, gave 2,2,7-trimethoxy-2H-1-benzopyran 1a in 55% overall yield from 25. A similar methylation/methoxide sequence using 3-(2'-benzyloxy-4'-methoxyphenyl)-N-methyl-N-phenylpropanamide 18 gave a mixture which contained trimethyl 3-(2'-benzyloxy-4'-methoxyphenyl)orthopropanoate 20a and reaction of this mixture with a solution of sodium in tert-butanol gave a product in which 2,2,7-trimethoxy-2H-1-benzopyran 1a was detected, but not isolable. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00007-0
• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 在 三乙基硅烷 、 palladium 10% on activated carbon 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 β-(2-Hydroxy-4-methoxy-phenyl)-propionsaeure
  参考文献：
  名称：

  钌催化的分子内芳烃C（sp 2）–H酰胺化反应合成3,4-Dihydroquinolin-2（1 H）-ones

  摘要：

  我们报道了[Ru（对-cymene）（l-脯氨酸）Cl]（[Ru1]）催化的1,4,2-二恶唑-5-酮环化反应形成二氢喹啉-2-酮，具有优异的产率和极好的区域选择性通过正式的分子内芳烃C（sp 2）–H酰胺化。2-和4-取代的芳基二恶唑酮的反应首先通过在芳烃位点上的亲电酰胺化的螺内酰胺化进行，该芳烃位点对取代基是对位的或邻位的。Hammett相关性研究表明，螺内酰胺化可能是由于对苯丙氨酸的亲电子亚硝基化合物攻击而发生的，其特征是-0.73的负ρ值。

  DOI：

  10.1021/acs.orglett.1c00781

文献信息

• Synthesis of Lactams via Ir-Catalyzed C–H Amidation Involving Ir-Nitrene Intermediates
  作者：Jitian Liu、Wenjing Ye、Shuojin Wang、Junrong Zheng、Weiping Tang、Xiaoxun Li

  DOI：10.1021/acs.joc.0c00157

  日期：2020.3.20

  We have developed a divergent strategy for the synthesis of five- and six-membered lactams via either an amidation of sp3 C-H bonds or electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.

  我们已经开发了一种通过sp3 CH键的酰胺化或Ir-nitrene中间体亲电取代芳烃来合成五元和六元内酰胺的策略。通过在二氯甲烷或六氟-2-丙醇中使用易于获得的铱催化剂，以高至优异的产率和高选择性合成了多种内酰胺。
• Acylation and alkylation of 1,3-dimethoxybenzene in polyphosphoric acid
  作者：T. R. Kasturi、K. M. Damodaran

  DOI：10.1139/v69-252

  日期：1969.5.1

  Products of the reaction of 3-halo- and 3-ethoxypropionic acids with 1,3-dimethoxybenzene (4) in polyphosphoric acid have been shown to be 2′,4′-dimethoxy-3-(2,4-dimethoxyphenyl)-propiophenone (6) and 1,5-bis[3-(2,4-dimethoxyphenyl)-3-keto-propyl]-2,4-dimethoxybenzene (15) and these have been prepared by unambiguous syntheses. 2′,4′-Dimethoxy-3-ethoxypropiophenone (3a) and 2′,3,4′-trimethoxypropiophenone

  3-卤代和 3-乙氧基丙酸与 1,3-二甲氧基苯 (4) 在多磷酸中反应的产物已显示为 2',4'-二甲氧基-3-(2,4-二甲氧基苯基)-苯丙酮(6) 和 1,5-双[3-(2,4-二甲氧基苯基)-3-酮-丙基]-2,4-二甲氧基苯 (15) 和这些是通过明确的合成制备的。2',4'-二甲氧基-3-乙氧基苯丙酮 (3a) 和 2',3,4'-三甲氧基苯丙酮 (3d) 已通过 3-氯-2',4'-二甲氧基苯丙酮 (3c) 的反应合成分别用乙醇和甲醇。
• Enzymatic synthesis of kavalactones and flavokavains
  申请人：Whitehead Institute for Biomedical Research

  公开号：US10941429B2

  公开（公告）日：2021-03-09

  Disclosed are methods, compositions, proteins, nucleic acids, cells, vectors, compounds, reagents, and systems for the preparation of kavalactones, flavokavains, and kavalactone and flavokavain biosynthetic intermediates using enzymes expressed in heterologous host cells, such as microorganisms or plants, or using in vitro enzymatic reactions. This invention also provides for the expression of the enzymes by recombinant cell lines and vectors. Furthermore, the enzymes can be components of constructs such as fusion proteins. The kavalactones produced can be utilized to treat anxiety disorder, insomnia, and other psychological and neurological disorders. The flavokavains produced can be utilized to treat various cancers including colon, bladder, and breast cancers.

  本发明公开了利用在异源宿主细胞（如微生物或植物）中表达的酶或利用体外酶促反应制备卡瓦内酯、黄酮素以及卡瓦内酯和黄酮素生物合成中间体的方法、组合物、蛋白质、核酸、细胞、载体、化合物、试剂和系统。本发明还提供了通过重组细胞系和载体表达酶的方法。此外，酶还可以是融合蛋白等构建体的组成部分。生产的卡瓦内酯可用于治疗焦虑症、失眠症以及其他心理和神经疾病。生产的黄酮类化合物可用于治疗各种癌症，包括结肠癌、膀胱癌和乳腺癌。
• Langley; Adams, Journal of the American Chemical Society, 1922, vol. 44, p. 2327
  作者：Langley、Adams

  DOI：——

  日期：——
• ENZYMATIC SYNTHESIS OF KAVALACTONES AND FLAVOKAVAINS
  申请人：Whitehead Institute for Biomedical Research

  公开号：US20190271015A1

  公开（公告）日：2019-09-05

  Disclosed are methods, compositions, proteins, nucleic acids, cells, vectors, compounds, reagents, and systems for the preparation of kavalactones, flavokavains, and kavalactone and flavokavain biosynthetic intermediates using enzymes expressed in heterologous host cells, such as microorganisms or plants, or using in vitro enzymatic reactions. This invention also provides for the expression of the enzymes by recombinant cell lines and vectors. Furthermore, the enzymes can be components of constructs such as fusion proteins. The kavalactones produced can be utilized to treat anxiety disorder, insomnia, and other psychological and neurological disorders. The flavokavains produced can be utilized to treat various cancers including colon, bladder, and breast cancers.