N-[2-(3,4-dihydroxyphenyl)ethyl]-4-methoxybenzamide | 1541168-57-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: N-[2-(3,4-dihydroxyphenyl)ethyl]-4-methoxybenzamide
• 英文别名: N-(3,4-dihydroxyphenethyl)-4-methoxybenzamide
• CAS: 1541168-57-3
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: FAKHLFHAZMTVEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  78.79
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[2-(3,4-dihydroxyphenyl)ethyl]-4-methoxybenzamide 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-(2-<3,4-dimethoxyphenyl>-ethyl)-p-methoxybenzamide
  参考文献：
  名称：

  具有高对映选择性的无阻且非电子丰富的1-芳基二氢异喹啉的不对称转移加氢。

  摘要：

  在1位上含有间位或对位取代的芳族基团的二氢异喹啉（DHIQ）的不对称转移氢化（ATH）中，使用在TsDPEN上带有杂环基的芳烃/ Ru / TsDPEN催化剂会导致生成高对映体过量。以前，只有1-（邻位取代的）芳基DHIQ，或带有富电子的稠合环，才能得到高对映选择性的产物。因此，这种方法解决了亚胺ATH的长期挑战。

  DOI：

  10.1021/acs.orglett.0c02034
• 作为产物：
  描述：

  4-methoxybenzoic acid 2,5-dioxo-1-pyrrolidinyl ester 、 盐酸多巴胺 在 碳酸氢钠 作用下， 以 水 为溶剂， 生成 N-[2-(3,4-dihydroxyphenyl)ethyl]-4-methoxybenzamide
  参考文献：
  名称：

  3D-QSAR study of adamantyl N-benzylbenzamides as melanogenesis inhibitors

  摘要：

  Three-dimensional quantitative structure-activity relationship (3D-QSAR) modeling, comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA) of polyhydroxylated N-benzylbenzamide derivatives containing an adamantyl moiety were performed to understand the mechanism of action and structure-activity relationship of these compounds. Contour map analysis indicated that steric contributions of the adamantyl moiety and electrostatic contributions of the hydroxyl group at the 3-position are important in the activity. Activities of the training set and test sets predicted by CoMFA fit well with actual activities, demonstrating that CoMFA, along with the best calculated q(2) value, has the best predictive ability. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.056

文献信息

• 3D-QSAR study of adamantyl N-benzylbenzamides as melanogenesis inhibitors
  作者：Yong Deog Hong、Heung Soo Baek、Haelim Cho、Soo Mi Ahn、Ho Sik Rho、Young-Ho Park、Yung Hyup Joo、Song Seok Shin

  DOI：10.1016/j.bmcl.2013.11.056

  日期：2014.1

  Three-dimensional quantitative structure-activity relationship (3D-QSAR) modeling, comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA) of polyhydroxylated N-benzylbenzamide derivatives containing an adamantyl moiety were performed to understand the mechanism of action and structure-activity relationship of these compounds. Contour map analysis indicated that steric contributions of the adamantyl moiety and electrostatic contributions of the hydroxyl group at the 3-position are important in the activity. Activities of the training set and test sets predicted by CoMFA fit well with actual activities, demonstrating that CoMFA, along with the best calculated q(2) value, has the best predictive ability. (C) 2013 Elsevier Ltd. All rights reserved.
• Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity
  作者：Jonathan Barrios-Rivera、Yingjian Xu、Martin Wills

  DOI：10.1021/acs.orglett.0c02034

  日期：2020.8.21

  The use of arene/Ru/TsDPEN catalysts bearing a heterocyclic group on the TsDPEN in the asymmetric transfer hydrogenation (ATH) of dihydroisoquinolines (DHIQs) containing meta- or para-substituted aromatic groups at the 1-position results in the formation of products of high enantiomeric excess. Previously, only 1-(ortho-substituted)aryl DHIQs, or with an electron-rich fused ring gave products with

  在1位上含有间位或对位取代的芳族基团的二氢异喹啉（DHIQ）的不对称转移氢化（ATH）中，使用在TsDPEN上带有杂环基的芳烃/ Ru / TsDPEN催化剂会导致生成高对映体过量。以前，只有1-（邻位取代的）芳基DHIQ，或带有富电子的稠合环，才能得到高对映选择性的产物。因此，这种方法解决了亚胺ATH的长期挑战。