(3S)-3-<(p-methoxybenzyl)-oxy>-butanoic acid | 170649-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S)-3-<(p-methoxybenzyl)-oxy>-butanoic acid
• 英文别名: (S)-3-(4-methoxybenzyloxy)butanoic acid；(3S)-3-[(4-methoxyphenyl)methoxy]butanoic acid
• CAS: 170649-30-6
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: HUNKWCDBPQDQCZ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-3-<(p-methoxybenzyl)-oxy>-butanoic acid 在 氯化亚砜 作用下， 以 环己烷 为溶剂， 反应 1.0h， 生成 (3S)-3-<(p-methoxybenzyl)oxy>-butanoic acid chloride
  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：

  (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

文献信息

• Design and synthesis of a macrosphelide A-biotin chimera
  作者：Hwayoung Yun、Jaehoon Sim、Hongchan An、Jeeyeon Lee、Hun Seok Lee、Young Kee Shin、Seung-Mann Paek、Young-Ger Suh

  DOI：10.1039/c4ob01028k

  日期：——

  The rational design and synthesis of a biochemical probe of natural (+)-macrosphelide A, a potent cell–cell adhesion inhibitor, was completed to aid in the identification of its biological target. The key features of the synthesis include: (1) an efficient synthesis of the macrosphelide core structure using Yamaguchi–Hirao alkynylation, (2) a cross metathesis to connect a linker unit to the allyl-macrosphelide and (3) coupling of the linker-bound macrosphelide A with a chemical biotin tag.

  完成了天然活性化合物(+)-大环孢素A（一种强效的细胞间粘附抑制剂）的合理设计和合成，以帮助鉴定其生物学靶点。合成关键特征包括：(1) 利用山口-平尾炔基化高效合成大环孢素核心结构，(2) 通过交叉复分解反应将连接单元与烯丙基大环孢素连接，以及 (3) 将连接单元结合的大环孢素A与化学生物素标签结合。
• Concise Syntheses of (+)-Macrosphelides A and B: Studies on the Macro-Ring Closure Strategy
  作者：Seung-Mann Paek、Hwayoung Yun、Nam-Jung Kim、Jong-Wha Jung、Dong-Jo Chang、Sujin Lee、Jakyung Yoo、Hyun-Ju Park、Young-Ger Suh

  DOI：10.1021/jo8016692

  日期：2009.1.16

  Highly concise syntheses of (+)-macrosphelides A and B were accomplished in this study. The key feature of our synthetic route involved the direct three-carbon homologation of the readily available Weinreb amide 6 by the addition of a trans-vinylogous ester anion equivalent and facile construction of the 16-membered macrolide skeleton of macrosphelides via an intramolecular nitrile oxide−olefin cycloaddition

  在这项研究中完成了（+）-大环内酯A和B的高度简洁的合成。我们合成路线的关键特征包括通过添加反式-乙烯基酯阴离子等价物和易于构建的Weinreb酰胺6的直接三碳同系物，以及通过分子内一氧化氮轻松构建大分子内酯的16元大环内酯骨架的方法-烯烃环加成。大衍生物A和B的合成分别以30％和20％的总产率完成。本文描述了我们合成的细节。
• First total syntheses of (−)-macrosphelides J and K and elucidation of their absolute configuration
  作者：Hwayoung Yun、Seung-Mann Paek、Jong-Wha Jung、Nam-Jung Kim、Seok-Ho Kim、Young-Ger Suh

  DOI：10.1039/b817693k

  日期：——

  First total syntheses of (–)-macrosphelides J and K and their structural elucidation are described.

  首次介绍了 (â)-macrosphelides J 和 K 的全合成及其结构解析。
• Synthetic Studies on Bioactive Natural Polyketides: Intramolecular Nitrile Oxide-Olefin Cycloaddition Approach for Construction of a Macrolactone Skeleton of Macrosphelide B
  作者：Seung-Mann Paek、Young-Ger Suh

  DOI：10.3390/molecules16064850

  日期：——

  of macrosphelide B via an intramolecular nitrile oxide-olefin cycloaddition (INOC) is described. In particular, an asymmetric INOC approach using phase transfer catalysts seems to be a potentially efficient and versatile procedure for the construction of the macrolactone skeleton of macrosphelide B in terms of facial selectivity. Our preliminary and unprecedented stereoselective procedure is anticipated

  描述了通过分子内腈氧化物-烯烃环加成 (INOC) 合成 macrosphelide B 的研究。特别是，就面部选择性而言，使用相转移催化剂的不对称 INOC 方法似乎是构建巨球体 B 的大环内酯骨架的潜在有效且通用的方法。我们的初步和前所未有的立体选择性程序有望通过进一步研究来有效地应用于合成大球体家族。
• Concise Syntheses of (+)-Macrosphelides A and B
  作者：Seung-Mann Paek、Seung-Yong Seo、Seok-Ho Kim、Jong-Wha Jung、Yong-Sil Lee、Jae-Kyung Jung、Young-Ger Suh

  DOI：10.1021/ol0508429

  日期：2005.7.1

  [reaction: see text]. Unified and highly convergent total syntheses of (+)-macrosphelides A and B are described. Key features of the syntheses include (1) concise synthesis of the optically active delta-hydroxy-gamma-keto alpha,beta-unsaturated acid fragment via the direct addition of a trans-vinylogous ester anion equivalent to the readily available Weinreb amide and (2) facile construction of the

  [反应：请参见文字]。描述了（+）-大环内酯A和B的统一且高度收敛的总合成。合成的关键特征包括（1）通过直接添加与容易获得的Weinreb酰胺相当的反式-乙烯基酯阴离子来简并合成旋光性δ-羟基-γ-酮基α，β-不饱和酸片段和（2 ）通过分子内腈氧化环加成（INOC）方便地构建大环内酯系列的16元大环内酯核。