1-(3,4,5-trimethoxyphenyl)pentan-1-one | 114085-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,4,5-trimethoxyphenyl)pentan-1-one
• 英文别名: 1-(3,4,5-Trimethoxy-phenyl)-pentan-1-on；1-(3,4,5-trimethoxyphenyl)-1-pentanone
• CAS: 114085-80-2
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: ZXCSAUWRJRVZLN-UHFFFAOYSA-N

物化性质

• 熔点：
  270 °C
• 沸点：
  190-192 °C(Press: 6 Torr)
• 密度：
  1.040±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  1-(3,4,5-trimethoxyphenyl)pentan-1-one 在 氢氧化钾 、 氢化钾 、 肼 作用下， 以 四氢呋喃 为溶剂， 反应 30.0h， 生成 橄榄醇二甲基醚
  参考文献：
  名称：

  1-n-烷基-3,4,5-三甲氧基苯的区域选择性4-脱甲氧基化：合成橄榄醇及其同系物的关键步骤

  摘要：

  在电子转移条件下选择性除去1-n-烷基-3,4,5-三甲氧基苯中的4-甲氧基。描述了橄榄醇二甲醚的新合成。

  DOI：

  10.1039/c39870001549
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酰乙酸乙酯 在 氢氧化钾 、 sodium ethanolate 作用下， 生成 1-(3,4,5-trimethoxyphenyl)pentan-1-one
  参考文献：
  名称：

  Asahina; Kusaka, Chemische Berichte, 1936, vol. 69, p. 450,452

  摘要：

  DOI：

文献信息

• Suzuki–Miyaura Coupling of Simple Ketones via Activation of Unstrained Carbon–Carbon Bonds
  作者：Ying Xia、Jianchun Wang、Guangbin Dong

  DOI：10.1021/jacs.8b02462

  日期：2018.4.25

  Here, we describe that simple ketones can be efficiently employed as electrophiles in Suzuki-Miyaura coupling reactions via catalytic activation of unstrained C-C bonds. A range of common ketones, such as cyclopentanones, acetophenones, acetone and 1-indanones, could be directly coupled with various arylboronates in high site-selectivity, which offers a distinct entry to more functionalized aromatic

  在这里，我们描述了通过催化激活无张力的 CC 键，简单的酮可以在 Suzuki-Miyaura 偶联反应中有效地用作亲电子试剂。一系列常见的酮，如环戊酮、苯乙酮、丙酮和1-茚满酮，可以直接与各种芳基硼酸酯以高位点选择性偶联，这为获得更多功能化的芳香酮提供了独特的途径。初步机理研究表明酮 α-CC 键通过氧化加成断裂。
• A New Synthesis of 1-<i>n</i>-Alkyl-3,5-dimethoxybenzenes (Olivetol Dimethyl Ether and Homologs)
  作者：Ugo Azzena、Teresa Denurra、Emma Fenude、Giovanni Melloni、Gloria Rassu

  DOI：10.1055/s-1989-27135

  日期：——

  An efficient method is reported for the synthesis of 1-n-alkyl-3,5-dimethoxybenzenes, useful intermediates in the synthesis of cannabinoids, from the readily available and cheap 3,4,5-trimethoxybenzoic acid. The key step is the electron-transfer induced highly regioselective demethoxylation of 1-n-alkyl-3,4,5-trimethoxybenzenes.

  报告了一种高效的方法，用于合成1-n-烷基-3,5-二甲氧基苯，这是一种在合成大麻素中有用的中间体，来源于易得且廉价的3,4,5-三甲氧基苯甲酸。关键步骤是电子转移诱导的高区域选择性去甲氧基反应，针对1-n-烷基-3,4,5-三甲氧基苯。
• Propenone derivatives
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05952355A1

  公开（公告）日：1999-09-14

  The present invention relates to propenone derivatives represented by the following formula (I): ##STR1## wherein R.sup.1 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, or YR.sup.5 (wherein Y represents S or O; and R.sup.5 represents substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a substituted or unsubstituted cyclic ether residue); R.sup.2 and R.sup.3 independently represent hydrogen, lower alkyl, or substituted or unsubstituted aralkyl, or alternatively R.sup.2 and R.sup.3 are combined to form substituted or unsubstituted methylene or ethylene; R.sup.4 represents hydrogen, hydroxy, lower alkyl, substituted or unsubstituted aralkyl, lower alkoxy, substituted or unsubstituted aralkyloxy, or halogen; and X represents substituted or unsubstituted indolyl; or pharmaceutically acceptable salts thereof.

  本发明涉及由以下式（I）表示的丙酮衍生物：##STR1## 其中R.sup.1表示氢，取代或未取代的低级烷基，取代或未取代的芳基，或YR.sup.5（其中Y表示S或O; R.sup.5表示取代或未取代的低级烷基，取代或未取代的芳基，取代或未取代的杂环芳基，或取代或未取代的环状醚残基）; R.sup.2和R.sup.3分别表示氢，低级烷基，或取代或未取代的芳基烷基，或者R.sup.2和R.sup.3结合形成取代或未取代的亚甲基或乙烯基; R.sup.4表示氢，羟基，低级烷基，取代或未取代的芳基烷基，低级烷氧基，取代或未取代的芳基烷氧基，或卤素; X表示取代或未取代的吲哚基; 或其药学上可接受的盐。
• PROPENONE DERIVATIVE
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0680950A1

  公开（公告）日：1995-11-08

  A propenone derivative represented by general formula (I) and a pharmacologically acceptable salt thereof, wherein R¹ represents hydrogen, lower alkyl, lower alkanoyl, lower alkoxycarbonyl, lower alkylsulfonyl, aralkyl, (un)substituted aroyl, (un)substituted arylsulfonyl, (un)substituted heteroarylcarbonyl, (un)substituted heteroarylsulfonyl, diglycolyl or a group of formula (a), R² represents hydrogen, lower alkyl, halogen, (un)substituted aryl or (un)substituted heteroaryl; R³ represents hydrogen, lower alkyl or (un)substituted aryl; and R⁴, R⁵, R⁶ and R⁷ represent each independently hydrogen, lower alkyl, lower alkoxy, aralkyloxy, hydroxy, nitro, halogen, trifluoromethyl or -NR⁸R⁹, wherein R⁸ and R⁹ represent each independently hydrogen, lower alkyl, lower alkanoyl, lower alkoxycarbonyl or (un)substituted aroyl.

  一种由通式(I)代表的丙烯酮衍生物及其药理学上可接受的盐，其中 R¹ 代表氢、低级烷基、低级烷酰基、低级烷氧羰基、低级烷基磺酰基、芳烷基、(未)取代的芳烷基、(未)取代的芳烷基磺酰基、(未)取代的杂芳基羰基、(未)取代的杂芳基磺酰基、二缩烷基或式(a)基团、(R²代表氢、低级烷基、卤素、（未）取代的芳基或（未）取代的杂芳基；R³ 代表氢、低级烷基或（未）取代的芳基；和 R⁴、R⁵、R⁶ 和 R⁷ 各自独立地代表氢、低级烷基、低级烷氧基、芳氧基、羟基、硝基、卤素、三氟甲基或 -NR⁸R⁹，其中 R⁸ 和 R𠞙 各自独立地代表氢、低级烷基、低级烷酰基、低级烷氧羰基或（未）取代的芳基。
• Constructing novel dihydrofuran and dihydroisoxazole analogues of isocombretastatin-4 as tubulin polymerization inhibitors through [3+2] reactions
  作者：Ming-Yu Song、Chen-Yu Cao、Qiu-Rui He、Qing-Miao Dong、Ding Li、Jiang-Jiang Tang、Jin-Ming Gao

  DOI：10.1016/j.bmc.2017.07.048

  日期：2017.10

  [3+2] reactions play a key role in constructing various pharmaceutical moleculars. In this study, using Mn (OAc)(3) mediated and 1,3-dipolar [3+2] cyclization reactions, 38 novel dihydrofuran and dihydroisoxazole analogues of isoCA-4 were synthesized as inhibitors of tubulin polymerization. Among them, compound 6g was found to be the most potent cytotoxic agents against PC-3 cells with IC50 value of 0.47 mu M, and compound 5p exhibted highest activity on HeLa cells with IC50 vaule of 2.32 mu M. Tubulin polymerization assay revealed that 6g was a dose-dependent and effective inhibitor of tubulin assembly. Immunohistochemistry studies and cell cycle distribution analysis indicated that 6g severely disrupted microtubule network and significantly arrested most cells in the G2/M phase of the cell cycle in PC-3 cells. In addition, molecular docking studies showed that two chiral isomers of 6g can bind efficiently and similarly at colchicine binding site of tubulin. (C) 2017 Elsevier Ltd. All rights reserved.