6-(4-methoxybenzyloxy)hexanoic acid | 343221-33-0

• 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: 6-(4-methoxybenzyloxy)hexanoic acid
• 英文别名: 6-[(4-Methoxyphenyl)methoxy]hexanoic acid
• CAS: 343221-33-0
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: AQQWHWWVQFSNGT-UHFFFAOYSA-N

物化性质

• 沸点：
  398.6±27.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  6-(4-methoxybenzyloxy)hexanoic acid 在 碳酸氢钠 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 18.25h， 生成 methyl 2-(6-hydroxyhexanoylamino)acetate
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin D

  摘要：

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.

  DOI：

  10.1021/jo047732k
• 作为产物：
  描述：

  6-((4-甲氧基苄基)氧基)己酸甲酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以90%的产率得到6-(4-methoxybenzyloxy)hexanoic acid
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin D

  摘要：

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.

  DOI：

  10.1021/jo047732k

文献信息

• Tandem Oxidation-Dehydrogenation of (Hetero)Arylated Primary Alcohols via Perruthenate Catalysis
  作者：Christian J. Bettencourt、Sharon Chow、Peter W. Moore、Christopher D. G. Read、Yanxiao Jiao、Jan Peter Bakker、Sheng Zhao、Paul V. Bernhardt、Craig M. Williams

  DOI：10.1071/ch21137

  日期：——

  Tandem oxidative-dehydrogenation of primary alcohols to give α,β-unsaturated aldehydes in one pot are rare transformations in organic synthesis, with only two methods currently available. Reported herein is a novel method using the bench-stable salt methyltriphenylphosphonium perruthenate (MTP3), and a new co-oxidant NEMO·PF6 (NEMO = N-ethyl-N-hydroxymorpholinium) which provides unsaturated aldehydes

  伯醇的串联氧化脱氢在一锅中得到 α,β-不饱和醛是有机合成中罕见的转化，目前只有两种方法可用。本文报道了一种使用长期稳定的过钌酸甲基​​三苯基鏻盐 (MTP3) 和新的助氧化剂 NEMO·PF 6 (NEMO =  N-乙基-N-羟基吗啉) 的新方法，该方法以低到中等的收率提供不饱和醛。使用N-氧化物助氧化剂 NMO (NMO =  N-甲基吗啉N-氧化物)/NEMO对（杂）芳基化伯醇进行 Ley-Griffith 氧化，通过添加N-氧化物盐 NEMO·PF 6得到扩展将中间体饱和醛转化为其不饱和对应物。重点介绍了该方法的发现、方法开发、反应范围和相关挑战。通过合成与辅助结合蛋白 B 相关的多烯支架，证明了天然产物合成后期脱氢的概念价值。
• Evolution of a Protecting-Group-Free Total Synthesis: Studies en Route to the Neuroactive Marine Macrolide (−)-Palmyrolide A
  作者：Rodolfo Tello-Aburto、Tara D. Newar、William A. Maio

  DOI：10.1021/jo301121f

  日期：2012.7.20

  neuroactive marine macrolide (−)-palmyrolide A is described. Our first-generation approach aimed to unlock the unknown C(5)–C(7) stereochemical relationship via the synthesis of four diastereomers of palmyrolide A aldehyde, a known degradation product. When these efforts provided inconclusive results, recourse to synthesizing all possible stereocombinations of the 15-membered macrolide was undertaken.

  描述了我们对神经活性海洋大环内酯（-）-palmyrolide A的第一个全合成的合成工作的完整说明。我们的第一代方法旨在通过合成已知的降解产物Palmyrolide A醛的四种非对映异构体来解锁未知的C（5）-C（7）立体化学关系。当这些努力提供不确定的结果时，便采取了合成15元大环内酯类化合物所有可能的立体组合的方法。这些研究对于确认绝对立体化学至关重要，可以产生第一个（+）- ent- palmyrolide A的全合成。在这项工作之后，还报道了第一个无保护基的天然（-）-palmyrolide A的全合成。 。
• Liposomal Formulation of Retinoids Designed for Enzyme Triggered Release
  作者：Palle J. Pedersen、Sidsel K. Adolph、Arun K. Subramanian、Ahmad Arouri、Thomas L. Andresen、Ole G. Mouritsen、Robert Madsen、Mogens W. Madsen、Günther H. Peters、Mads H. Clausen

  DOI：10.1021/jm100190c

  日期：2010.5.13

  The design of retinoid phospholipid prodrugs is described based on molecular dynamics simulations and cytotoxicity studies of synthetic retinoid esters. The prodrugs are degradable by secretory phospholipase A(2) IIA and have potential in liposomal drug delivery targeting tumors. We have synthesized four different retinoid phospholipid prodrugs and shown that they form particles in the liposome size region with average diameters of 94-118 nm. Upon subjection to phospholipase A(2), the lipid prodrugs were hydrolyzed, releasing cytotoxic retinoids and lysolipids. The formulated lipid prodrugs displayed IC50 values in the range of 3-19 mu M toward HT-29 and Colo205 colon cancer cells in the presence of phospholipase A(2), while no significant cell death was observed in the absence of the enzyme.
• HOYE T. R.; KURTH M. J.; LO V., TETRAHEDRON LETT., 1981, 22, NO 9, 815-818
  作者：HOYE T. R.、 KURTH M. J.、 LO V.

  DOI：——

  日期：——
• Total Synthesis of (+)-Crocacin D
  作者：Luiz C. Dias、Luciana G. de Oliveira、Janaína D. Vilcachagua、Florian Nigsch

  DOI：10.1021/jo047732k

  日期：2005.3.1

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.