N,N-二乙基-3,4,5-三甲氧基苯甲酰胺 | 5470-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N-二乙基-3,4,5-三甲氧基苯甲酰胺
• 英文名称: N,N-diethyl-3,4,5-trimethoxybenzamide
• CAS: 5470-42-8
• 化学式: C₁₄H₂₁NO₄
• mdl: MFCD00584586
• 分子量: 267.325
• InChiKey: OGUSJMCQDBTOPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N,N-二乙基-3,4,5-三甲氧基苯甲酰胺 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以10%的产率得到3,4,5-三甲氧基苯甲醛
  参考文献：
  名称：

  用氢化二异丁基铝控制将活化的伯酰胺和仲酰胺还原为醛

  摘要：

  公开了一种在甲苯中使用氢化二异丁基铝 (DIBAL-H) 将活化的伯酰胺和仲酰胺还原为醛的实用方法。多种芳基和烷基N -Boc 、N, N-diBoc和N-甲苯磺酰基酰胺以良好至极好的产率转化为相应的醛。发现对还原敏感的官能团如硝基、氰基、烯烃和炔烃基团是稳定的。广泛的底物范围、官能团兼容性和快速转换是该方法的显着特点。

  DOI：

  10.1039/d1ob02414k
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸 在 草酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N,N-二乙基-3,4,5-三甲氧基苯甲酰胺
  参考文献：
  名称：

  用氢化二异丁基铝控制将活化的伯酰胺和仲酰胺还原为醛

  摘要：

  公开了一种在甲苯中使用氢化二异丁基铝 (DIBAL-H) 将活化的伯酰胺和仲酰胺还原为醛的实用方法。多种芳基和烷基N -Boc 、N, N-diBoc和N-甲苯磺酰基酰胺以良好至极好的产率转化为相应的醛。发现对还原敏感的官能团如硝基、氰基、烯烃和炔烃基团是稳定的。广泛的底物范围、官能团兼容性和快速转换是该方法的显着特点。

  DOI：

  10.1039/d1ob02414k

文献信息

• A Mixed Naphthyl-Phenyl Phosphine Ligand Motif for Suzuki, Heck, and Hydrodehalogenation Reactions
  作者：Oleg Demchuk、Victor Snieckus、Bilge Yoruk、Tom Blackburn

  DOI：10.1055/s-2006-951538

  日期：2006.11

  Nap-Phos, representing a new naphthyl-phenyl biaryl-type phosphine ligand class and available by a short synthesis (4 steps, 71% overall yield), effectively catalyzes the Suzuki-Miyaura (including highly hindered cases), hydrodehalogenation, and Heck reactions.

  Nap-Phos代表着一种新型萘基-苯基双芳基膦配体，可通过短合成路线（4步，总产率71%）制备，并能有效催化铃木-宫浦反应（包括高度受阻的情况）、氢去卤反应和赫克反应。
• A Direct and Mild Conversion of Tertiary Aryl Amides to Methyl Esters Using Trimethyloxonium Tetrafluoroborate: A Very Useful Complement to Directed Metalation Reactions
  作者：Gary E Keck、Mark D McLaws、Travis T Wager

  DOI：10.1016/s0040-4020(00)00969-8

  日期：2000.12

  of tertiary amides directly to methyl esters has been investigated. The process involves a two-step, one pot procedure in which a tertiary amide is first treated with trimethyloxonium tetrafluoroborate to generate an imidate intermediate which is then hydrolyzed, generally by the addition of saturated aqueous sodium bicarbonate solution. Although this process fails for aliphatic amides, very good yields

  已经研究了将叔酰胺直接转化为甲酯的直接方法的范围和一般性。该方法包括两步一锅法，其中首先用四氟硼酸三甲基氧鎓处理叔酰胺以生成亚氨酸酯中间体，然后通常通过加入饱和的碳酸氢钠水溶液将其水解。尽管该方法对于脂肪族酰胺是失败的，但是对于衍生自芳族羧酸的各种酰胺都实现了非常好的收率。在N-烷基上的立体位阻是很好的耐受性。因此，N，N-二甲基，-二乙基和-二异丙基酰胺均可被成功利用。
• A Regioselective Synthesis of Dimethyl Phthalide-3-phosphonates
  作者：Mitsuaki Watanabe、Saori Ijichi、Sunao Furukawa

  DOI：10.1055/s-1993-25807

  日期：——

  Dimethyl phthalide-3-phosphonates having various substituents on the benzene ring were regioselectively synthesized by the reaction of N,N-diethyl-2-formylbenzamides with tert-butyldimethylsilyl dimethyl phosphite followed by treatment with methanesulfonic acid. N,N-Diethyl-2-formylbenzamides were regioselectively prepared by ortho lithiation-formylation of the corresponding benzamides.

  具有不同取代基的二甲基邻苯二甲酸酯-3-膦酸酯通过N,N-二乙基-2-甲酰基苯甲酰胺与叔丁基二甲基硅基二甲基膦酸酯反应，随后用甲磺酸处理，选择性合成。N,N-二乙基-2-甲酰基苯甲酰胺则通过相应苯甲酰胺的邻位锂化-甲酰化反应选择性制备。
• Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo
  作者：Alexander Sailer、Franziska Ermer、Yvonne Kraus、Rebekkah Bingham、Ferdinand H Lutter、Julia Ahlfeld、Oliver Thorn-Seshold

  DOI：10.3762/bjoc.16.14

  日期：——

  Background: Hemithioindigo is a promising molecular photoswitch that has only recently been applied as a photoswitchable pharmacophore for control over bioactivity in cellulo. Uniquely, in contrast to other photoswitches that have been applied to biology, the pseudosymmetric hemithioindigo scaffold has allowed the creation of both dark-active and lit-active photopharmaceuticals for the same binding site by a priori design. However, the potency of previous hemithioindigo photopharmaceuticals has not been optimal for their translation to other biological models.

  Results: Inspired by the structure of tubulin-inhibiting indanones, we created hemithioindigo-based indanone-like tubulin inhibitors (HITubs) and optimised their cellular potency as antimitotic photopharmaceuticals. These HITubs feature reliable and robust visible-light photoswitching and high fatigue resistance. The use of the hemithioindigo scaffold also permitted us to employ a para-hydroxyhemistilbene motif, a structural feature which is denied to most azobenzenes due to the negligibly short lifetimes of their metastable Z-isomers, which proved crucial to enhancing the potency and photoswitchability. The HITubs were ten times more potent than previously reported hemithioindigo photopharmaceutical antimitotics in a series of cell-free and cellular assays, and allowed robust photocontrol over tubulin polymerisation, microtubule (MT) network structure, cell cycle, and cell survival.

  Conclusions: HITubs represent a powerful addition to the growing toolbox of photopharmaceutical reagents for MT cytoskeleton research. Additionally, as the hemithioindigo scaffold allows photoswitchable bioactivity for substituent patterns inaccessible to the majority of current photopharmaceuticals, wider adoption of the hemithioindigo scaffold may significantly expand the scope of cellular and in vivo targets addressable by photopharmacology.

  背景：Hemithioindigo是一种有前途的分子光开关，最近才被应用作为细胞内生物活性控制的可光开关药效基团。与已应用于生物学的其他光开关相比，伪对称的Hemithioindigo骨架独特地通过先验设计允许在同一结合位点上创建暗活性和亮活性的光药物。然而，先前的Hemithioindigo光药物的效力对于它们在其他生物模型中的转化并不理想。 结果：受到抑制微管的吲哚酮结构的启发，我们创建了基于Hemithioindigo的类似吲哚酮的微管抑制剂（HITubs），并优化了它们作为抗有丝分裂光药物的细胞效力。这些HITubs具有可靠和强大的可见光光开关性能和高疲劳抗性。Hemithioindigo骨架的使用还使我们能够采用一个对大多数偶氮苯来说是被拒绝的para-羟基半亚苄基团，这对于增强效力和光开关性至关重要。在一系列无细胞和细胞实验中，HITubs比先前报道的Hemithioindigo光药物抗有丝分裂活性物质更有效，可以可靠地控制微管聚合、微管网络结构、细胞周期和细胞存活。 结论：HITubs是对微管细胞骨架研究不断增长的光药物试剂工具箱的强大补充。此外，由于Hemithioindigo骨架允许对大多数当前光药物无法访问的取代模式进行光开关生物活性，广泛采用Hemithioindigo骨架可能显著扩大细胞和体内靶标的范围，从而扩展光药理学的适用范围。
• Magnetic CuFe2O4 nanoparticles: a retrievable catalyst for oxidative amidation of aldehydes with amine hydrochloride salts
  作者：A. Suresh Kumar、B. Thulasiram、S. Bala Laxmi、Vikas S. Rawat、B. Sreedhar

  DOI：10.1016/j.tet.2014.01.051

  日期：2014.9

  for the oxidative amidation of aldehydes with amine hydrochloride salts is described. A wide range of amides have been synthesized in good to excellent yields under mild conditions. Chiral amide also synthesized from its corresponding chiral amine salt with retention of the stereochemistry. In particular, the performance of the magnetic separation of the catalyst was very efficient and an alternative

  描述了磁性CuFe 2 O 4纳米颗粒在醛与胺盐酸盐的氧化酰胺化中的应用。在温和的条件下，已经以良好的收率合成了各种酰胺。还从其相应的手性胺盐合成了手性酰胺，并且保留了立体化学。特别地，催化剂的磁分离性能非常有效，并且可以替代时间，溶剂和耗能的分离程序。连续五个周期后，催化剂的催化活性保持不变，由于其效率，易处理性和成本效益，使其在环境方面无害且可广泛应用。