4-methoxydecanoic acid | 1190596-18-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-methoxydecanoic acid
• CAS: 1190596-18-9
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: MRHBORFTGZDAGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  4-methoxydecanoic acid 、 二苯甲基哌嗪 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以70%的产率得到1-(4-benzhydrylpiperazin-1-yl)-4-methoxydecan-1-one
  参考文献：
  名称：

  Synthesis and Antifungal Activity of (±)-4-Methoxy Decanoic Acid and Its Novel Amide Derivatives

  摘要：

  A simple synthetic route has been developed for fatty acid, (+/-)-4-methoxy decanoic acid (1), in 4 steps with 42% overall yield. The novel amide derivatives of 1 are synthesized. The in vitro antifungal activity of 1 and its novel amide derivatives 1a-1f has been evaluated against different organisms. Compounds 1e, 1f exhibited antifungal activity higher than the parent compound 1 against macrophomina phaseolina, and 1a, 1d exhibited antifungal activity against sclerotium rolfsii.

  DOI：

  10.1134/s1070363218030222
• 作为产物：
  描述：

  1,2-环氧辛烷 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 dimethyl sulfide borane 、 sodium hydride 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 12.75h， 生成 4-methoxydecanoic acid
  参考文献：
  名称：

  Synthesis and Antifungal Activity of (±)-4-Methoxy Decanoic Acid and Its Novel Amide Derivatives

  摘要：

  A simple synthetic route has been developed for fatty acid, (+/-)-4-methoxy decanoic acid (1), in 4 steps with 42% overall yield. The novel amide derivatives of 1 are synthesized. The in vitro antifungal activity of 1 and its novel amide derivatives 1a-1f has been evaluated against different organisms. Compounds 1e, 1f exhibited antifungal activity higher than the parent compound 1 against macrophomina phaseolina, and 1a, 1d exhibited antifungal activity against sclerotium rolfsii.

  DOI：

  10.1134/s1070363218030222

文献信息

• Total synthesis of racemic and (R) and (S)-4-methoxyalkanoic acids and their antifungal activity
  作者：Biswanath Das、Digambar Balaji Shinde、Boddu Shashi Kanth、Avijeet Kamle、C. Ganesh Kumar

  DOI：10.1016/j.ejmech.2011.04.045

  日期：2011.7

  The total synthesis of 4-methoxydecanoic acid and 4-methoxyundecanoic acid in racemic and stereoselective [(R) and (S)] forms has been accomplished. For stereoselective synthesis of the compounds (S) and (R)-BINOL complexes have been used to generate the required chiral centres. The antifungal activity of these compounds has been studied against different organisms and the results were found to be impressive

  已完成外消旋和立体选择性[（R）和（S）]形式的4-甲氧基癸酸和4-甲氧基十一烷酸的全合成。为了立体选择性地合成化合物（S）和（R）-BINOL，已使用配合物生成所需的手性中心。已经研究了这些化合物对不同生物的抗真菌活性，结果令人印象深刻。比较了外消旋和立体选择性形式的化合物的活性。（R）-4-甲氧基癸酸被发现是最有效的（MIC：白色念珠菌MTCC 227，白色念珠菌MTCC 4748，巴西曲霉（Aspergillus brasiliensis）的MIC：0.019 mg / mL（niger）MTCC 281和Issatchenkia Orientalis MTCC 3020）。
• The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid
  作者：Néstor M. Carballeira、Carlos Miranda、Keykavous Parang

  DOI：10.1016/j.tetlet.2009.07.074

  日期：2009.10

  The hitherto unknown (+/-)-4-methoxydecanoic acid was synthesized in six steps and in 25% overall yield starting from commercially available 4-penten-1-ol. The title compound demonstrated 17-fold higher antifungal activity (MIC = 1.5 mu M) against Candida albicans ATCC 60193 and Cryptococcus neoformans ATCC 66031 when compared to unsubstituted n-decanoic acid. Our results demonstrate that mid-chain methoxylation appears to be a viable strategy for increasing the fungitoxicity of fatty acids. (C) 2009 Elsevier Ltd. All rights reserved.
• US3953514A
  申请人：——

  公开号：US3953514A

  公开（公告）日：1976-04-27
• [EN] A USE OF BARBITURIC ACID DERIVATIVES AS HERBICIDAL EFFICACY-ENHANCING AGENTS OR HERBICIDAL AGENTS AND PROCESS FOR THEIR PREPARATION<br/>[FR] UTILISATION DE DÉRIVÉS D'ACIDE BARBITURIQUE EN TANT QU'AGENTS AUGMENTANT L'EFFICACITÉ D'HERBICIDES OU EN TANT QU'AGENTS HERBICIDES ET PROCÉDÉ DE SYNTHÈSE DESDITS DÉRIVÉS
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2007068352A1

  公开（公告）日：2007-06-21

  [EN] Barbituric acid derivatives of the formula (I): or salts thereof, wherein, R¹ represents C_4-I2 alkyl which is unsubstituted or substituted with C_1-4 alkoxy; C_5-9 alkenyl or C_5-9 alkynyl; R² represents methyl or ethyl; R³ represents methyl or ethyl; and X represents O or S can be used as herbicidal efficacy-enhancing agents, and some of which can be used as herbicides. Some compounds being embraced by the formula (I) are also claimed. The herbicidally effective compounds show very quick effective action.
  [FR] Des dérivés d'acide barbiturique de formule (I) : ou des sels desdits dérivés, où R¹ représente un groupement alkyle en C₄-C₁₂ éventuellement substitué par un groupement alkoxy en C₁-C₄ ; un groupement alcényle en C₅-C₉ ou un groupement alcynyle en C₅-C₉ ; R² représente un groupement méthyle ou éthyle ; R³ représente un groupement méthyle ou éthyle ; et X représente O ou S, peuvent être employés en tant qu'agents augmentant l'efficacité des herbicides, certains d'entre eux pouvant être employés en tant qu'herbicides. Certains composés englobés par la formule (I) sont également revendiqués par l'invention. Les composés à action herbicide présentent un effet important et très rapide.
• Synthesis and Antifungal Activity of (±)-4-Methoxy Decanoic Acid and Its Novel Amide Derivatives
  作者：N. J. P. Subhashini、P. Ashok Kumar、Ch. Bhaskar Reddy、B. Lingaiah、Hameeda Bee

  DOI：10.1134/s1070363218030222

  日期：2018.3

  A simple synthetic route has been developed for fatty acid, (+/-)-4-methoxy decanoic acid (1), in 4 steps with 42% overall yield. The novel amide derivatives of 1 are synthesized. The in vitro antifungal activity of 1 and its novel amide derivatives 1a-1f has been evaluated against different organisms. Compounds 1e, 1f exhibited antifungal activity higher than the parent compound 1 against macrophomina phaseolina, and 1a, 1d exhibited antifungal activity against sclerotium rolfsii.