(S)-3-((4-甲氧基苄基)氧基)丁酸乙酯 | 170649-26-0

• 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: (S)-3-((4-甲氧基苄基)氧基)丁酸乙酯
• 英文名称: (S)-3-(4-Methoxy-benzyloxy)-butyric acid ethyl ester
• 英文别名: ethyl (3S)-3-[(4-methoxyphenyl)methoxy]butanoate
• CAS: 170649-26-0
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: NJPHUTKAIVLMRG-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  8
• 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：

  (S)-3-((4-甲氧基苄基)氧基)丁酸乙酯 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以88%的产率得到(3S)-3-<(p-methoxybenzyl)-oxy>-butanoic acid
  参考文献：
  名称：

  An efficient synthesis of radicinin analogues

  摘要：

  We describe herein an enantio- and diastereoselective total synthesis of two radicinin analogues 13 and 14. 13 has been subjected to biological tests, exhibiting the lowest toxicity of all radicinin analogues that have been investigated to date and it depresses the heart ventricular strip and histamine contraction, The key reaction to establish the radicinin skeleton is the reduction of the pseudo C-2 symmetrical precursor 11 with the aid of TiCl4 and LiBH4.

  DOI：

  10.1016/0040-4020(95)00491-p
• 作为产物：
  描述：

  4-甲氧基苄醇 在 氢氧化钾 、 三氟甲磺酸三甲基硅酯 、 三(3,6-二氧杂庚基)胺 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.17h， 生成 (S)-3-((4-甲氧基苄基)氧基)丁酸乙酯
  参考文献：
  名称：

  An Efficient Method for thep-Methoxybenzylation of Hydroxy Groups with 2-(4-Methoxybenzyloxy)-3-nitropyridine

  摘要：

  2-(4-甲氧基苄氧基)-3-硝基吡啶（PMBONPy），由2-氯-3-硝基吡啶和4-甲氧基苄醇（PMB）轻松制备，在催化量的三甲基硅基三氟甲磺酸酯（Me3SiOTf）存在下，与各种类型的羟基反应，在温和条件下以高产率生成相应的PMB醚。

  DOI：

  10.1246/cl.2001.424

文献信息

• Natural Product-Guided Synthesis of a Spiroacetal Collection Reveals Modulators of Tubulin Cytoskeleton Integrity
  作者：Okram Barun、Kamal Kumar、Stefan Sommer、Anette Langerak、Thomas U. Mayer、Oliver Müller、Herbert Waldmann

  DOI：10.1002/ejoc.200500605

  日期：2005.11

  underlying structural skeleton of numerous biologically active natural products. Since simplified but characteristic spiroketals derived from the parent natural products retain biological activity, the spiro[5.5]ketal unit can be regarded as a biologically prevalidated framework for the development of natural product-derived compound collections. We report an enantioselective synthesis of spiro[5.5]ketals

  螺[5.5]缩酮部分构成了许多具有生物活性的天然产物的基本结构骨架。由于源自母体天然产物的简化但特征性的螺缩酮保留了生物活性，螺[5​​.5]缩酮单元可被视为开发天然产物衍生化合物集合的生物学预验证框架。我们报告了螺[5.5] 缩酮在固体载体上的对映选择性合成。反应序列采用不对称硼烯醇醇醛醇反应，烯醇与聚合物结合或在溶液中作为关键的对映分化步骤。它在固体载体上进行多达 12 个步骤，以高总产率和高立体选择性获得所需的螺缩酮，并且可以适应产品的结构变化。合成的小型 spiroketal 集合包含磷酸酶抑制剂和调节人癌细胞中微管蛋白细胞骨架形成的化合物，而不直接靶向微管。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Solution and solid phase p-alkoxybenzylation of alcohols under neutral conditions
  作者：Stephen Hanessian、Huynh Hoan Khai

  DOI：10.1016/s0040-4039(98)02531-3

  日期：1999.1

  Primary, secondary, and tertiary alcohols can be converted to p-methoxybenzyl ethers under neutral conditions in the presence of a variety of commonly used functional and protective groups. The method can be adapted to solid phase on a Wang resin, (C) 1999 Elsevier Science Ltd. All rights reserved.
• Total Synthesis of Virgatolide B
  作者：Paul A. Hume、Daniel P. Furkert、Margaret A. Brimble

  DOI：10.1021/ol402191t

  日期：2013.9.6

  The first total synthesis of the benzannulated spiroketal virgatolide A is presented. Key features include sp(3)-sp(2) Suzuki coupling of an enantiomerically enriched beta-trifluoroboratoamide and an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction followed by global deprotection/cyclization with regioselectivity governed by internal hydrogen bonding.
• FUSED CYCLIC COMPOUNDS AND USE THEREOF
  申请人：[en]JACOBIO PHARMACEUTICALS CO., LTD.

  公开号：WO2024120433A1

  公开（公告）日：2024-06-13

  The invention relates to fused cyclic compounds, a composition containing the same and the use thereof.
• An efficient synthesis of radicinin analogues
  作者：Marcus Eh、Dietmar Schomburg、Kathrin Schicht、Markus Kalesse

  DOI：10.1016/0040-4020(95)00491-p

  日期：1995.8

  We describe herein an enantio- and diastereoselective total synthesis of two radicinin analogues 13 and 14. 13 has been subjected to biological tests, exhibiting the lowest toxicity of all radicinin analogues that have been investigated to date and it depresses the heart ventricular strip and histamine contraction, The key reaction to establish the radicinin skeleton is the reduction of the pseudo C-2 symmetrical precursor 11 with the aid of TiCl4 and LiBH4.