methyl 2-(3-methoxybenzyl)-3-oxobutanoate | 1350653-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 2-(3-methoxybenzyl)-3-oxobutanoate
• 英文别名: methyl 2-[(3-methoxyphenyl)methyl]-3-oxobutanoate；Methyl 2-(3-methoxybenzyl)-3-oxobutanoate
• CAS: 1350653-48-3
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: WVKZSZXJMZHRPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-methoxybenzyl)-3-oxobutanoate 在 吡啶 、 三溴化硼 、 铜 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl 2-{3-[(1-methyl-1H-benzimidazol-2-yl)methoxy]benzyl}-3-oxobutanoate
  参考文献：
  名称：

  Design and Synthesis of Benzimidazole-Linked meta-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities

  摘要：

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.678461
• 作为产物：
  描述：

  methyl 2-(3-methoxybenzylidene)-3-oxobutanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、137.9 kPa 条件下， 反应 45.0h， 以85%的产率得到methyl 2-(3-methoxybenzyl)-3-oxobutanoate
  参考文献：
  名称：

  Design and Synthesis of Benzimidazole-Linked meta-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities

  摘要：

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.678461

文献信息

• 7-HYDROXY-PYRAZOLO[1,5-A] PYRIMIDINE COMPOUNDS AND THEIR USE AS CCR2 RECEPTOR ANTAGONISTS
  申请人：Boyd Joe William

  公开号：US20130252951A1

  公开（公告）日：2013-09-26

  The compounds of formula (I) are antagonists of the CCR2 receptor Wherein R 1-7 and A are as defined in the claims.

  式(I)的化合物是CCR2受体的拮抗剂，其中R1-7和A如权利要求中所定义。
• Catalytic Asymmetric Homologation of Ketones with α-Alkyl α-Diazo Esters
  作者：Fei Tan、Maoping Pu、Jun He、Jinzhao Li、Jian Yang、Shunxi Dong、Xiaohua Liu、Yun-Dong Wu、Xiaoming Feng

  DOI：10.1021/jacs.0c12683

  日期：2021.2.10

  derivatives with α-alkyl α-diazo esters utilizing a chiral scandium(III) N,N′-dioxide as the Lewis acid catalyst. This reaction supplies a highly chemo-, regio-, and enantioselective pathway for the synthesis of optically active β-keto esters with an all-carbon quaternary center through highly selective alkyl-group migration of the ketones. Moreover, the ring expansion of cyclic ketones was accomplished under

  酮与重氮化合物的同源性是合成单碳扩链无环酮或扩环环酮的有用策略。然而，由于较低的反应性和复杂的选择性，无环酮与α-重氮酯的不对称同源性仍然是一个挑战。在此，我们报道了利用手性scan（III）N，N与N -α-烷基α-重氮酯对苯乙酮和相关衍生物的对映选择性催化同源性'-二氧化物为路易斯酸催化剂。该反应提供了高度化学，区域和对映体选择性的途径，用于通过酮的高选择性烷基基团迁移来合成具有全碳季中心的旋光性β-酮酯。此外，环状酮的扩环是在稍微修饰的条件下完成的，从而提供了一系列对映体富集的环状β-酮酯。已经进行了密度泛函理论计算，以阐明可以解释所观察到的区域和对映选择性的反应途径和可能的工作模型。
• Catalytic Enantioselective Protonation/Nucleophilic Addition of Diazoesters with Chiral Oxazaborolidinium Ion Activated Carboxylic Acids
  作者：Ki-Tae Kang、Seung Tae Kim、Geum-Sook Hwang、Do Hyun Ryu

  DOI：10.1002/anie.201612655

  日期：2017.3.27

  A new chiral Brønsted acid derived from carboxylic acid and a chiral oxazaborolidinium ion (COBI), as an activator, is introduced. This acid was successfully applied as a catalyst for the highly enantioselective protonation/nucleophilic addition of diazoesters with carboxylic acids.

  引入了一种新的手性布朗斯台德酸，其衍生自羧酸和手性恶唑硼烷鎓离子（COBI）作为活化剂。该酸已成功地用作重氮酸酯与羧酸的高度对映选择性质子化/亲核加成的催化剂。
• Direct benzylation of 1,3-dicarbonyl compounds catalyzed by Cs_2.5H_0.5PW₁₂O₄₀ in solvent-free conditions
  作者：Ezzat Rafiee、Maryam Khodayari、Mohammad Joshaghani

  DOI：10.1139/v11-134

  日期：2011.12

  improved modification of the direct benzylation of 1,3-carbonyl compounds in terms of low reaction times, solvent-free conditions, usage of a small amount of the catalyst, and a clean reaction profile. Furthermore, the use of this catalyst is feasible because of its easy preparation, its easy handling, its stability, its easy recovery, its reusability, being environmentally green, its excellent activity

  在 Cs2.5H0.5PW12O40 盐的存在下，各种 1,3-二羰基化合物很容易与苄醇反应，以高产率生成 2-苄基-1,3-二羰基化合物。发现这种催化剂可以完全回收和再利用而不会损失其催化活性，因此具有环保意识，尤其是在无溶剂条件下。在低反应时间、无溶剂条件、使用少量催化剂和干净的反应曲线方面，该方法的使用提供了对 1,3-羰基化合物的直接苄基化的改进改进。此外，这种催化剂的使用是可行的，因为它易于制备、易于处理、稳定性、易于回收、可重复使用、环境绿色、活性优良、选择性好。
• 12-Tungstophosphoric acid supported on nano silica from rice husk ash as an efficient catalyst for direct benzylation of 1,3-dicarbonyl compounds in solvent-free condition
  作者：Ezzat Rafiee、Maryam Khodayari、Shabnam Shahebrahimi、Mohammad Joshaghani

  DOI：10.1016/j.molcata.2011.10.008

  日期：2011.12

  12-Tungstophosphoric acid, H3PW12O40 (PW) has been supported on this silica to produce nano silica supported PW (NPW/SiO2) as a nano catalyst. Characterization of this catalyst has been investigated by TEM, FTIR, and ICP, also, acidic properties have been studied by potentiometric titration method. 40% NPW/SiO2 has been used as a high effective catalyst for benzylation of 1,3-dicarbonyl compounds with benzylic

  纳米二氧化硅是由稻壳制成的，稻壳是一种农业废料，具有高表面积和无定形形式。在该二氧化硅上负载有12钨磷酸H 3 PW 12 O 40（PW），以生产作为纳米催化剂的纳米二氧化硅负载的PW（NPW / SiO 2）。通过TEM，FTIR和ICP对这种催化剂的表征进行了研究，并且通过电位滴定法对酸性进行了研究。40％NPW /二氧化硅2已被用作高效的催化剂，用于用苄醇对1，3-二羰基化合物进行苄基化。本方法提供了在无溶剂条件下的清洁，实用，简单，温和，环保，绿色且省时的方法。同样，该催化剂是大规模用于1，3-二羰基化合物的直接苄基化的良好选择。