N-pentanoyl-N-[4-(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2'-yl)benzyl]-L-valinemethyl ester | 883223-09-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-pentanoyl-N-[4-(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2'-yl)benzyl]-L-valinemethyl ester
• 英文别名: (S)-methyl 3-methyl-2-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)pentanamido)butanoate；N-pentanoyl-N-[4-(4',4',5',5'-tetramethyl-1',3',2'-dioxaborolan-2'-yl)benzyl]-L-valine methyl ester；methyl N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl-4-yl-methyl]-N-pentanoyl-L-valinate；methyl (2S)-3-methyl-2-[pentanoyl-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]amino]butanoate
• CAS: 883223-09-4
• 化学式: C₂₄H₃₈BNO₅
• 分子量: 431.38
• InChiKey: QRFXXPFMFWHOKV-NRFANRHFSA-N

物化性质

• 沸点：
  539.3±45.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-pentanoyl-N-[4-(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2'-yl)benzyl]-L-valinemethyl ester 在 四(三苯基膦)钯 sodium hydroxide 、 sodium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 19.0h， 生成 缬沙坦
  参考文献：
  名称：

  缬沙坦的有效合成，一种非肽类血管紧张素 II 受体拮抗剂

  摘要：

  描述了一种合成血管紧张素 II 受体拮抗剂缬沙坦 (1) 的高效收敛方法，缬沙坦是当今抗高血压治疗中最重要的药物之一。4-溴甲苯的直接邻位金属化提供了关键的硼酸中间体 11，该中间体经过钯催化的 Suzuki 偶联。这种方法克服了与先前报道的合成相关的许多缺点。缬沙坦中甲酯的皂化反应简便、经济，更适合工业化生产。

  DOI：

  10.1055/s-2006-926234
• 作为产物：
  描述：

  L-缬氨酸甲酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 N-pentanoyl-N-[4-(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2'-yl)benzyl]-L-valinemethyl ester
  参考文献：
  名称：

  Microwave-Mediated Synthesis of an Arylboronate Library

  摘要：

  A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.

  DOI：

  10.1021/co100011g

文献信息

• Polymer-Supported Electron-Rich Oxime Palladacycle as an Efficient Heterogeneous Catalyst for the Suzuki Coupling Reaction
  作者：Hong-Jun Cho、Sungwon Jung、Saerom Kong、Sung-Jun Park、Sang-Myung Lee、Yoon-Sik Lee

  DOI：10.1002/adsc.201300499

  日期：2014.3.24

  heterogeneous catalysts were employed for the Suzuki coupling reaction of aryl halides with arylboronic acids. The electron‐richness of the oxime ligand was controlled by the substituted alkoxy groups. Evaluation based on the electronic effect of the catalysts revealed that the alkoxy‐substituted oxime palladacycle resins showed better catalytic activity than palladated Kaiser oxime resin in the Suzuki coupling

  各种设计为非均相催化剂的富电子肟化合物都被用于芳基卤化物与芳基硼酸的Suzuki偶联反应。肟配体的电子富集度受取代的烷氧基控制。根据催化剂的电子效应进行的评估表明，在铃木偶联反应中，烷氧基取代的肟四面环化合物比钯酸化的Kaiser肟树脂具有更好的催化活性，并且肟基四面环树脂的催化活性随肟配体的电子富集度的增加而增加。增加。尽管其系统异构，但最富电子的肟型四环铝环氧化物树脂对合成联芳基和杂联芳基化合物均表现出出色的催化性能。作为催化剂的实际应用，在温和条件下以高收率合成了缬沙坦前体。富电子肟树脂也可以重复使用最多5个循环，同时在Suzuki偶联反应中保持良好的催化活性。
• [EN] BIARYLMETHYL HETEROCYCLES<br/>[FR] HÉTÉROCYCLES BIARYLMÉTHYLES
  申请人：UNIV MONTREAL

  公开号：WO2018005591A1

  公开（公告）日：2018-01-04

  The present invention provides compounds of Formula (I): wherein all variables are as defined in the specification, and compositions comprising any of such novel compounds. These compounds are biased agonists, or β-Arrestin agonists of the angiotensin II receptor, which may be used as medicaments.

  本发明提供了式(I)的化合物：其中所有变量如规范中所定义，并包括任何此类新化合物的组合物。这些化合物是肾素II受体的偏倚激动剂，或β-阻滞素激动剂，可用作药物。
• Convenient Synthesis of Valsartan via a Suzuki Reaction
  作者：Samir Ghosh、A. Sanjeev Kumar、G. N. Mehta

  DOI：10.3184/030823410x12698758703526

  日期：2010.4

  An efficient synthesis of the angiotensin II inhibitor Valsartan (Diovan) is presented. The formation of the aryl–aryl bond represents the key step of its synthesis, which has been done by a Suzuki coupling of aryl boronate with 2-bromophenyl oxazoline with good yield and purity. This method overcomes many of the drawbacks associated with the previously reported syntheses.

  本文介绍了血管紧张素 II 抑制剂缬沙坦（Diovan）的高效合成方法。芳基芳基键的形成是其合成的关键步骤，该步骤是通过硼酸芳基酯与 2-溴苯基噁唑啉的铃木偶联完成的，具有良好的收率和纯度。这种方法克服了以前报道的合成方法的许多缺点。
• WO2006/67216
  申请人：——

  公开号：——

  公开（公告）日：——
• Microwave-Mediated Synthesis of an Arylboronate Library
  作者：John Spencer、Christine B. Baltus、Hiren Patel、Neil J. Press、Samantha K. Callear、Louise Male、Simon J. Coles

  DOI：10.1021/co100011g

  日期：2011.1.10

  A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 11-3) respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.