6-(4-methoxyphenyl)-hexan-1-oic acid | 107228-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-(4-methoxyphenyl)-hexan-1-oic acid
• 英文别名: 6-(4-methoxyphenyl)hexanoic acid；6-(p-anisyl)hexanoic acid；6-(4-methoxy-phenyl)-hexanoic acid；6-(4-Methoxy-phenyl)-hexansaeure；6-p-Anisylcapronsaeure
• CAS: 107228-87-5
• 化学式: C₁₃H₁₈O₃
• mdl: MFCD12172613
• 分子量: 222.284
• InChiKey: GYLAUURZVLOHNI-UHFFFAOYSA-N

物化性质

• 熔点：
  47-49 °C
• 沸点：
  383.4±25.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-methoxyphenyl)-hexan-1-oic acid 在 lithium aluminium tetrahydride 、 四溴化碳 、 三苯基膦 作用下， 生成 1-(6-溴己基)-4-甲氧基苯
  参考文献：
  名称：

  Materials chemistry of chiral macromolecules. 1. Synthesis and phase transitions

  摘要：

  This paper describes work on synthesis of chiral macromolecules as part of a materials chemistry study which seeks to establish links in these systems among molecular structure, three-dimensional molecular organization, and properties. The basic materials chemistry hypothesis driving this work is that chiral forces among stereogenic centers may serve as guiding fields to organize polymers in two or three dimensions. It follows that physical properties could be directly or indirectly controlled by chirality. In order to promote strong forces among chiral centers the chains were designed to have stereogenic carbons substituted by the strongly dipolar cyano group and spaced by 16 atoms along the backbone. The preparative chemistry of chiral macromolecules is challenging given the limited number of polymerization methodologies and the inherent translational periodicity of synthetic polymers. We have synthesized here low symmetry chiral macromolecules in which the only symmetry element retained is polar translation; achiral homologues lacking the nitrile function, the configurationally disordered polymer, and dimeric model compounds were prepared as well. The compounds exhibited crystalline and liquid crystalline phases, and significant differences were observed among homologues through differential scanning calorimetry and optical microscopy. The substitution of nitrile groups every 16 atoms along the polymer backbone, specially with configurational disorder, leads to glassy or less ordered condensed phases. In some Polymers when the strongly dipolar stereogenic centers do not have preferred handedness, chains organize into mesophases rather than crystalline structures. This is surprising since the concentration of stereogenic centers is extremely dilute. Using dimeric model compounds, homochiral recognition among stereogenic centers with large dipole moments was identified as an important factor in the assembly of molecules into layered structures. Interestingly, catenation of the dipolar stereogenic centers in polymeric compounds apparently leads to layered structures even when configurational disorder exists along the polymer backbone. This type of structural control could be extremely useful as an approach to tune physical properties of polymeric materials.

  DOI：

  10.1021/ja00035a041
• 作为产物：
  描述：

  4-羧丁基三苯基溴化膦 在 palladium 10% on activated carbon 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 21.75h， 生成 6-(4-methoxyphenyl)-hexan-1-oic acid
  参考文献：
  名称：

  高效N-酰基乙醇胺酸酰胺酶（NAAA）抑制剂的鉴定：恶唑烷酮衍生物的末端苯基部分的优化

  摘要：

  ñ-酰基乙醇胺酸酰胺酶（NAAA）是半胱氨酸水解酶，参与脂肪酸乙醇酰胺（如棕榈酰乙醇酰胺（PEA））的失活。NAAA抑制可为治疗需要更高PEA水平的疾病提供潜在的治疗策略。在本研究中，我们报道了恶唑烷酮衍生物作为NAAA抑制剂的结构-活性关系（SAR）研究。研究了恶唑烷酮衍生物的末端苯环的一系列取代基或烷基取代基。结果表明，这些恶唑烷酮衍生物对NAAA的抑制能力取决于末端基团的大小，柔韧性和亲脂性。SAR结果表明，较小的亲脂性3-苯基取代基或含羟基的4-苯基取代基对于获得最佳效价是优选的。此外，出于高抑制效力，也优选远端脂肪族替代物。快速稀释和动力学分析表明，具有不同末端苯基部分的恶唑烷酮衍生物通过不同的机理抑制NAAA。这项研究确定了几种高效的NAAA抑制剂，包括1a（F215，IC 50  = 0.009μM ），1o（IC 50  = 0.061μM）和2e（IC 50  = 0.0

  DOI：

  10.1016/j.ejmech.2017.08.004

文献信息

• Benzoquinone derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04897420A1

  公开（公告）日：1990-01-30

  Compounds of the formula: ##STR1## wherein l is an integer of 0 to 18, X is hydrogen, an alkyl having 1 to 4 carbon atoms or a carboxylic acyl having 2 to 4 carbon atoms and Y is a phenylene, a cycloalkylene having 3 to 7 carbon atoms or a group of the formula: ##STR2## in which m is an integer of 0 to 3, and R.sub.1 and R.sub.2 each is an alkyl having 1 to 4 carbon atoms, are novel compounds, possess circulatory disturbance-improving activity and inhibitory activity of the generation and release of SRS-A, and used for prophylactic or therapy of ischemic diseases such as cerebral apoplexy or allergic diseases.

  该公式的化合物：##STR1## 其中 l 是0到18的整数，X 是氢，具有1到4个碳原子的烷基或具有2到4个碳原子的羧基酰基，Y 是苯基，具有3到7个碳原子的环烷基或具有以下公式的基团：##STR2## 其中 m 是0到3的整数，R.sub.1 和 R.sub.2 各自是具有1到4个碳原子的烷基，是新颖的化合物，具有改善循环障碍活性和抑制SRS-A的生成和释放活性，并用于预防或治疗脑卒中或过敏性疾病等缺血性疾病。
• Synthesis, metabolism, and in Vitro biological activities of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (CV-2619)-related compounds.
  作者：KAYOKO OKAMOTO、MASAZUMI WATANABE、HIROSHI MORIMOTO、ISUKE IMADA

  DOI：10.1248/cpb.36.178

  日期：——

  Demethyl dirivatives (3a and 3b) of 6(10-hydroxydecyl)-2, 3-dimethoxy-5-methyl-1, 4-benzoquinone (1, CV-2619), demethyl derivative (4) of the metabolite 2-4, and compounds (13, 20, 21, 23a and 23b) in which the hydroxyalkyl chain of 1 is modified, were synthesized for metabolic studies and evaluation of their biological activities. In rats, 13 and trans-23a were metabolized more slowly than 1. These compounds, except for the demethyl derivatives (3a, 3b and 4), showed an electron tansfer effect comparable to that of 1 in the succinate oxidation system. Compounds 13 and 23b inhibited the lipid peroxidation of rat liver homogenate.

  合成了 6（10-羟基癸基）-2，3-二甲氧基-5-甲基-1，4-苯醌（1，CV-2619）的二甲基衍生物（3a 和 3b）、代谢物 2-4 的二甲基衍生物（4），以及 1 的羟基烷基链发生改变的化合物（13、20、21、23a 和 23b），用于代谢研究和生物活性评估。除去甲基衍生物（3a、3b 和 4）外，这些化合物在琥珀酸氧化系统中显示出与 1 相当的电子转移效应。化合物 13 和 23b 可抑制大鼠肝匀浆的脂质过氧化反应。
• Chemistry of the β-Thiolactones: Substituent and Solvent Effects on Thermal Decomposition and Comparison with the β-Lactones.
  作者：Amandine Noel、Bernard Delpech、David Crich

  DOI：10.1021/jo500577c

  日期：2014.5.2

  tetraalkyl β-thiolactones and β-lactones is described as well as their thermal decomposition with extrusion of carbon oxysulfide and carbon dioxide in two solvents of opposite polarities. The β-thiolactones are considerably more thermally stable than the β-lactones and require higher temperatures for efficient decomposition in both solvents, whatever the degree of substitution. The results are interpreted

  描述了一系列二，三和四烷基β-硫代内酯和β-内酯的合成，以及它们在极性相反的两种溶剂中通过氧化氧硫化碳和二氧化碳的挤出而热分解的方法。β-硫代内酯比β-内酯具有更高的热稳定性，并且无论取代度如何，都需要更高的温度才能在两种溶剂中有效分解。用两性离子的断裂机理解释了结果，两个序列之间的速率确定步骤发生了变化。
• Fully Aqueous and Air-Compatible Cross-Coupling of Primary Alkyl Halides with Aryl Boronic Species: A Possible and Facile Method
  作者：Samuel Molyneux、Rebecca J. M. Goss

  DOI：10.1021/acscatal.3c00252

  日期：2023.5.5

  air by using simple and commercially available bench-stable reagents. The trisulfonated aryl phosphine TXPTS in combination with a water-soluble palladium salt Na2PdCl4 allowed for the Suzuki–Miyaura coupling of water-soluble alkyl halides with aryl boronic acids, boronic esters, and borofluorate salts in mild, fully aqueous conditions. Multiple challenging functionalities, including unprotected amino

  水相转化具有许多优点，包括减少环境影响和增加生物分子调节的机会。尽管已经进行了几项研究以实现芳基卤化物在水性条件下的交叉偶联，但迄今为止，催化工具箱中缺少在水性条件下伯烷基卤化物交叉偶联的方法，并且被认为是不可能的。水中的卤代烷偶联遇到严重的问题。其原因包括β-氢化物消除的强烈倾向、对空气和水高度敏感的催化剂和试剂的需要，以及许多亲水基团对交叉偶联条件的不耐受。在这里，我们报告了一种广泛适用且易于使用的方法，通过使用简单且市售的实验室稳定试剂来交叉偶联水和空气中的水溶性卤代烷。三磺化芳基膦 TXPTS 与水溶性钯盐 Na 2 PdCl 4结合，可在温和、完全水性的条件下实现水溶性卤代烷与芳基硼酸、硼酸酯和氟硼酸盐的 Suzuki-Miyaura 偶联。多种具有挑战性的功能，包括未受保护的氨基酸、肽内的非天然卤代氨基酸以及除草剂，可以在水中多样化。结构复杂的天然产物被用作试验台，展示海洋天然
• Fieser et al., Journal of the American Chemical Society, 1948, vol. 70, p. 3177
  作者：Fieser et al.

  DOI：——

  日期：——