methyl 5-(tetradecyloxy)furan-2-carboxylate | 54857-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methyl 5-(tetradecyloxy)furan-2-carboxylate
• 英文别名: 5-tetradecyloxy-2-furoic acid methyl ester；methyl 5-tetradecoxyfuran-2-carboxylate
• CAS: 54857-90-8
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.488
• InChiKey: CCFWTBDAOMJZKC-UHFFFAOYSA-N

物化性质

• 熔点：
  56-58 °C(Solv: methanol (67-56-1))
• 沸点：
  428.6±25.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  24
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(十四烷基氧)-2-糠酸 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 methyl 5-(tetradecyloxy)furan-2-carboxylate
  参考文献：
  名称：

  Hypolipidemic agents RO- or RS- substituted furoic acids, esters and

  摘要：

  以下一般结构的取代呋酸和酯及其药用可接受盐可用作降脂药物：其中Y代表氧或二价硫；R代表含有从10到20个碳原子的直链或支链烷基链，可以是饱和的，也可以是不饱和的，含有从1到4个双键；R.sup.1代表氢，含有从1到6个碳原子的直链或支链较低的烷基，苄基，苯乙基，吡啶基甲基，含有从3到6个碳原子的烷基多聚物，1,2,3,4,5,6-环己烷六基，或Z；Z代表(A)组##STR2##其中n是2或3的整数；R.sup.2代表含有从1到4个碳原子的直链或支链较低的烷基，或酰基；R.sup.3代表氢或含有从1到4个碳原子的直链或支链较低的烷基，但当R.sup.3为氢时，R.sup.2为酰基；或当R.sup.2不是酰基时，R.sup.2和R.sup.3与各自连接的氮原子一起形成单环杂环基团，如吡咯啉基，哌啶基，吗啉基或哌嗪基；或(B)组##STR3##其中整数M和P的总和等于3到5；R.sup.4代表含有从1到4个碳原子的直链或支链较低的烷基；X是从1到6的整数，但当R.sup.1为烷基多聚物或1,2,3,4,5,6-环己烷六基时，X等于2到6，当R.sup.1不是烷基多聚物或1,2,3,4,5,6-环己烷六基时，X等于1。

  公开号：

  US04110351A1

文献信息

• [EN] DERMATOLOGICAL FORMULATIONS OF 2-(2-ETHOXY-2-OXOETHYL)(METHYL)AMINO-2-OXOETHYL 5-(TETRADECYLOXY)FURAN-2-CARBOXYLATE<br/>[FR] FORMULATIONS DERMATOLOGIQUES DE 2-(2-ÉTHOXY-2-OXOÉTHYL)(MÉTHYL)AMINO-2-OXOÉTHYL5-(TÉTRADÉCYLOXY)FURAN-2-CARBOXYLATE
  申请人：DERMIRA INC

  公开号：WO2018022797A1

  公开（公告）日：2018-02-01

  Disclosed herein are dermatological formulations comprising low-impurity TOFA prodrug 2-(2-ethoxy-2-oxoethyl)(methyl)amino-2-oxoethyl 5-(tetradecyloxy)furan-2-carboxylate represented by Formula (la) and pharmaceutical use thereof.

  本文揭示了含有低杂质TOFA前药2-(2-乙氧基-2-氧代乙基)(甲基)氨基-2-氧代乙基-5-(十四烷氧基)呋喃-2-羧酸酯（化学式为la）的皮肤科配方及其药用。
• Synthesis of spiroketals under neutral conditions via a type III ring-rearrangement metathesis strategy
  作者：Jérémie Mandel、Nathalie Dubois、Markus Neuburger、Nicolas Blanchard

  DOI：10.1039/c1cc14329h

  日期：——

  A conceptually novel approach to spiro- and dispiroketals of various ring-sizes under neutral conditions has been designed which complements the classical thermodynamically driven tactic. Key steps involved the formation of α-alkoxyfurans, their [4+2] or [4+3] cycloaddition reactions and the ring-rearrangement metathesis of the resulting oxabicycles.

  我们设计了一种概念新颖的方法，可在中性条件下制备各种环尺寸的螺酮和二螺酮，这种方法是对经典热力学驱动策略的补充。关键步骤包括α-烷氧基呋喃的形成、其[4+2]或[4+3]环加成反应以及由此产生的氧杂双环的环重排偏析。
• [EN] TOFA ANALOGS USEFUL IN TREATING DERMATOLOGICAL DISORDERS OR CONDITIONS<br/>[FR] ANALOGUES DE TOFA UTILE DANS LE TRAITEMENT DE TROUBLES OU ÉTATS DERMATOLOGIQUES
  申请人：VALOCOR THERAPEUTICS INC

  公开号：WO2011005660A1

  公开（公告）日：2011-01-13

  This invention is directed to analogs of 5-(tetradecyloxy)-2-furancarboxylic acid (TOFA) and their use in the treatment of dermatological disorders or conditions characterized by sebaceous gland hyperactivity, such as acne and oily skin, and other dermatological disorders and conditions. This invention is also directed to pharmaceutical compositions comprising analogs of TOFA and a pharmaceutically acceptable excipient for dermatological or oral administration. Formula (I)

  本发明涉及5-(十四氧基)-2-呋喃羧酸（TOFA）的类似物及其在治疗皮肤病或由皮脂腺过度活跃引起的状况，如痤疮和油性皮肤，以及其他皮肤病和状况中的应用。本发明还涉及包含TOFA类似物和药用可接受的载体的制药组合物，用于皮肤或口服治疗。公式（I）
• Hypolipidemic composition and method of use
  申请人：Richardson-Merrell Inc.

  公开号：US04146623A1

  公开（公告）日：1979-03-27

  Substituted furoic acids and esters and pharmaceutically acceptable salts thereof of the following general structure are useful as hypolipidemic agents: ##STR1## wherein Y represents oxygen or divalent sulfur; R represents a straight or branched alkyl chain containing from 10 to 20 carbon atoms and may be saturated or may be unsaturated containing from 1 to 4 double bonds; R.sup.1 represents hydrogen, straight or branched lower alkyl of from 1 to 6 carbon atoms, benzyl, phenethyl, pyridylmethyl, alkane-poly-yl containing from 3 to 6 carbon atoms, 1,2,3,4,5,6-cyclohexanehexayl, or Z; Z represents ##STR2## wherein n is an integer of 2 or 3; R.sup.2 represents straight or branched lower alkyl of from 1 to 4 carbon atoms, or acyl; R.sup.3 represents hydrogen or straight or branched lower alkyl of from 1 to 4 carbon atoms with the proviso that when R.sup.3 is hydrogen, R.sup.2 is acyl; or when R.sup.2 is other than acyl, R.sup.2 and R.sup.3 taken together with the nitrogen atom to which each is attached form a monocyclic heterocyclic group, such as pyrrolidino, piperidino, morpholino, or piperazino; or ##STR3## wherein the sum of the integers m and p is equal to from 3 to 5; and R.sup.4 represents straight or branched lower alkyl of from 1 to 4 carbon atoms; X is an integer of from 1 to 6 with the proviso that when R.sup.1 is alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to from 2 to 6, and when R.sup.1 is other than alkane-poly-yl or 1,2,3,4,5,6-cyclohexanehexayl, X is equal to 1.

  以下一般结构的取代呋喃酸、酯和其药学上可接受的盐被用作降脂药物：其中，Y代表氧或二价硫；R代表含有10至20个碳原子的直链或支链烷基链，可以是饱和的或不饱和的，含有1至4个双键；R.sup.1代表氢、1至6个碳原子的直链或支链低烷基、苄基、苯乙基、吡啶甲基、含有3至6个碳原子的烷基多聚物、1,2,3,4,5,6-环己烷己基或Z；Z代表##STR2##其中n是2或3的整数；R.sup.2代表1至4个碳原子的直链或支链低烷基或酰基；R.sup.3代表氢或1至4个碳原子的直链或支链低烷基，但当R.sup.3为氢时，R.sup.2为酰基；或当R.sup.2不为酰基时，R.sup.2和R.sup.3与它们各自连接的氮原子一起形成单环杂环基团，如吡咯烷基、哌啶基、吗啉基或哌嗪基；或##STR3##其中整数m和p的总和等于3至5；R.sup.4代表1至4个碳原子的直链或支链低烷基；X是1至6的整数，但当R.sup.1为烷基多聚物或1,2,3,4,5,6-环己烷己基时，X等于2至6，当R.sup.1不为烷基多聚物或1,2,3,4,5,6-环己烷己基时，X等于1。
• TOFA ANALOGS USEFUL IN TREATING DERMATOLOGICAL DISORDERS OR CONDITIONS
  申请人：Daynard Timothy Scott

  公开号：US20120208807A1

  公开（公告）日：2012-08-16

  This invention is directed to analogs of 5-(tetradecyloxy)-2-furancarboxylic acid (TOFA) and their use in the treatment of dermatological disorders or conditions characterized by sebaceous gland hyperactivity, such as acne and oily skin, and other dermatological disorders and conditions. This invention is also directed to pharmaceutical compositions comprising analogs of TOFA and a pharmaceutically acceptable excipient for dermatological or oral administration. Formula (I)

  本发明涉及5-(十四氧基)-2-呋喃羧酸（TOFA）的类似物及其在治疗皮肤疾病或皮肤状况中的应用，包括皮肤痤疮和油性皮肤以及其他皮肤疾病和状况。本发明还涉及制备TOFA类似物的药物组合物，其中含有药用可接受的辅料，用于皮肤或口服给药。公式（I）