4-(2,3-dihydro-benzofuran-5-yl)-butyric acid | 121454-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 4-(2,3-dihydro-benzofuran-5-yl)-butyric acid
• 英文别名: 4-(2,3-Dihydro-benzofuran-5-yl)-buttersaeure；4-(2,3-dihydro-5-benzofuranyl)butanoic acid；4-(2,3-dihydrobenzofuran-5-yl)butanoic Acid；4-(2,3-dihydro-1-benzofuran-5-yl)butanoic acid
• CAS: 121454-72-6
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: PVDAXUSZNHTCHH-UHFFFAOYSA-N

物化性质

• 熔点：
  87 °C
• 沸点：
  220 °C(Press: 15 Torr)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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-(2,3-dihydro-benzofuran-5-yl)-butyric acid 在 ammonium hydroxide 、 草酰氯 、 dimethyl sulfide borane 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of Novel 6-Fluorochroman Derivatives as Potential 5-HT_1A Receptor Antagonists

  摘要：

  A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT1A receptor. N-2- [[(6-Fluorochroman-8-yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252-1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT1A receptor, some of which were selective with respect to alpha(1)-adrenergic and D-2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolin-stimulated adenylate cyclase assays in CHO cells expressing the human 5-HT1A receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screeds and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3-benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT-induced behavioral and electrophysiological responses in rats.

  DOI：

  10.1021/jm9707840
• 作为产物：
  描述：

  2,3-二氢苯并呋喃 在 盐酸 、 三氯化铝 、 mercury dichloride 、 锌 作用下， 以 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 8.0h， 生成 4-(2,3-dihydro-benzofuran-5-yl)-butyric acid
  参考文献：
  名称：

  对称吡啶离子的合成中形成的中间体的结构

  摘要：

  通过环状芳族酮与原甲酸乙酯反应合成对称的嵌段吡啶鎓衍生物，需要经过一定条件下可分离的中间体。当从1-四氢萘酮衍生物开始时，该中间体是不稳定的，但是令人惊讶的是，当用1-茚满酮衍生物进行合成时，可以很容易地分离出该中间体。此外，在后一种情况下，该中间体几乎不环化为预期的嵌段吡啶鎓衍生物。质谱和500 MHz 1 H和13证明了其离子结构C NMR技术包括杂核H CO CYY和DEPT极化转移实验。该中间体在乙醇水溶液中的水解在酸性或碱性介质中形成假碱，在后一种情况下，假碱与通过封闭的吡啶鎓离子的碱催化的开环所获得的强烈相似。在酸性和碱性溶液中，两种来源获得的假碱都显示相同的紫外可见吸收光谱。暂时解释了与由1-四氢萘酮衍生物形成的中间体相反，源自1-茚满酮衍生物的中间体（g）难以环化成封端的吡啶鎓结构。

  DOI：

  10.1002/poc.610081106

文献信息

• Pharmacologically active amino-5,6,7,8-tetrahydronaphtho [2,3-B] furan
  申请人：ADIR Et Cie

  公开号：US04863951A1

  公开（公告）日：1989-09-05

  Compounds of general formula I, ##STR1## in which: R.sub.1 denotes a hydrogen atom or, with the proviso, however, that the amino radical is at the 7-position, a linear or branched alkyl radical containing 1 to 4 carbon atoms, R.sub.2 denotes a hydrogen atom or, with the proviso, however, that the amino radical is at the 6-position, a linear or branched alkyl radical containing 1 to 4 carbon atoms, R.sub.3 and R.sub.4, which may be identical or different, each denote a hydrogen atom, a benzyl radical, a cyclohexylmethyl radical, a linear or branched alkylene radical containing from 1 to 5 carbon atoms, a linear or branched alkyl radical containing from 1 to 10 carbon atoms (optionally substituted with a hydroxy radical, with a carboxy radical or with an alkoxy radical having 1 to 5 carbon atoms, with an alkoxycarbonyl radical having 2 to 6 carbon atoms, with an anlkyphenyl radical or with an alkyl-2-theinyl radical), a halogenated alkyl radical containing from 1 to 5 carbon atoms, or form, together with the nitrogen to which they are attached, a 2-oxo-1-pyrrolidinyl radical, A-B denotes, with the oxygen to which it is attached, an ethyleneoxy radical, an ethynyleneoxy, a 2-oxo-1-oxyethylene radical or a 2-hydroxy-1-oxyethylene radical. The compounds of the formula I possess antidepressant, antiaggressive, and dopaminergic properties.

  通式I的化合物，##STR1##其中：R.sub.1表示氢原子或者，但是，氨基团位于7位时，含有1至4个碳原子的直链或支链烷基基团，R.sub.2表示氢原子或者，但是，氨基团位于6位时，含有1至4个碳原子的直链或支链烷基基团，R.sub.3和R.sub.4，可以相同也可以不同，每个都表示氢原子，苄基基团，环己基甲基基团，含有1至5个碳原子的直链或支链烷基基团，含有1至10个碳原子的直链或支链烷基基团（可选地用羟基基团，羧基基团或含有1至5个碳原子的烷氧基基团，含有2至6个碳原子的烷氧羰基基团，含有芳基基团或含有烷基-2-噻吩基团取代），含有1至5个碳原子的卤代烷基基团，或者与它们连接的氮原子一起形成2-氧代-1-吡咯啉基团，A-B表示与连接的氧原子一起，乙烯氧基基团，乙炔基氧基，2-氧代-1-氧乙烯基团或2-羟基-1-氧乙烯基团。通式I的化合物具有抗抑郁、抗攻击和多巴胺作用。
• Enantioselective biomimetic transamination of α-keto acids catalyzed by H4-naphthalene-derived axially chiral biaryl pyridoxamines
  作者：Chengkang Hou、Guoqing Zhao、Dongfang Xu、Baoguo Zhao

  DOI：10.1016/j.tetlet.2018.01.089

  日期：2018.3

  Asymmetric biomimetic transamination is a highly attractive method for synthesis of chemically and biologically important chiral amino acids and chiral amines. Development of chiral pyridoxamines/pyridoxals is the key for the reaction. New axially chiral biaryl pyridoxamines based on H4-naphathene skeleton have been developed. The pyridoxamines display good enantioselectivity and high catalytic activity

  不对称仿生转氨反应是合成化学和生物学上重要的手性氨基酸和手性胺的极具吸引力的方法。手性吡ido胺/吡rid醛的开发是反应的关键。已经开发了基于H 4-萘基骨架的新的轴向手性联芳基吡ido胺。吡ido胺在α-酮酸的不对称仿生转氨反应中表现出良好的对映选择性和高催化活性，可提供多种旋光性非天然氨基酸，产率为61-98％，ee可达91％。
• Structure of the intermediate formed in the synthesis of symmetrical pyrylium ions
  作者：M.-C. Gazeau、M. Simalty、P. Valat、V. Wintgens、J. Kossanyi、D. Doizi、G. Salvetat、J. Jaraudias、B. Perly、J. Vian、J.-L. Peglion

  DOI：10.1002/poc.610081106

  日期：1995.11

  The synthesis of symmetrical blocked pyrylium derivatives by reaction of a cyclic aromatic ketone with ethyl orthoformate goes through an intermediate which can be isolated under certain conditions. This intermediate is unstable when starting from 1-tetralone derivatives but, surprisingly, it can be isolated easily when the synthesis is performed with 1-indanone derivatives. Further, in the latter

  通过环状芳族酮与原甲酸乙酯反应合成对称的嵌段吡啶鎓衍生物，需要经过一定条件下可分离的中间体。当从1-四氢萘酮衍生物开始时，该中间体是不稳定的，但是令人惊讶的是，当用1-茚满酮衍生物进行合成时，可以很容易地分离出该中间体。此外，在后一种情况下，该中间体几乎不环化为预期的嵌段吡啶鎓衍生物。质谱和500 MHz 1 H和13证明了其离子结构C NMR技术包括杂核H CO CYY和DEPT极化转移实验。该中间体在乙醇水溶液中的水解在酸性或碱性介质中形成假碱，在后一种情况下，假碱与通过封闭的吡啶鎓离子的碱催化的开环所获得的强烈相似。在酸性和碱性溶液中，两种来源获得的假碱都显示相同的紫外可见吸收光谱。暂时解释了与由1-四氢萘酮衍生物形成的中间体相反，源自1-茚满酮衍生物的中间体（g）难以环化成封端的吡啶鎓结构。
• 2,4,5,6,7,8-Hexahydronaphtho[2,3-b]furan useful as an intermediate
  申请人：ADIR Et Cie

  公开号：US04885373A1

  公开（公告）日：1989-12-05

  Compounds of general formula I, ##STR1## in which: R.sub.1 denotes a hydrogen atom or, with the proviso, however, that the amino radical is at the 7-position, a linear or branched alkyl radical containing 1 to 4 carbon atoms, R.sub.2 denotes a hydrogen atom or, with the proviso, however, that the amino radical is at the 6-position, a linear or branched alkyl radical containing 1 to 4 carbon atoms, R.sub.3 and R.sub.4, which may be identical or different, each denote a hydrogen atom, a benzyl radical, a cyclohexylmethyl radical, a linear or branched alkylene radical containing from 1 to 5 carbon atoms, a linear or branched alkyl radical containing from 1 to 10 carbon atoms (optionally substituted with a hydroxy radical, with a carboxy radical or with an alkoxy radical having 1 to 5 carbon atoms, with an alkoxycarbonyl radical having 2 to 6 carbon atoms, with an alkylphenyl radical or with an alkyl-2-thienyl radical), a halogenated alkyl radical containing from 1 to 5 carbon atoms, or form, together with the nitrogen to which they are attached, a 2-oxo-1-pyrrolidinyl radical, A-B denotes, with the oxygen to which it is attached, an ethyleneoxy radical, an ethynyleneoxy, a 2-oxo-1-oxyethylene radical or a 2-hydroxy-1-oxyethylene radical. The compounds of Formula I possess antidepressant, antiggressive, and dopaminergic properties.

  通式I的化合物，其中：R.sub.1表示氢原子或，但是，如果氨基基团在7位，则表示含有1至4个碳原子的线性或支链烷基基团，R.sub.2表示氢原子或，但是，如果氨基基团在6位，则表示含有1至4个碳原子的线性或支链烷基基团，R.sub.3和R.sub.4可以相同也可以不同，分别表示氢原子，苯甲基基团，环己基甲基基团，含有1至5个碳原子的线性或支链烷基基团，含有1至10个碳原子的线性或支链烷基基团（可选择性地用羟基基团，羧基基团或具有1至5个碳原子的烷氧基基团，具有2至6个碳原子的烷氧羰基基团，烷基苯基基团或烷基-2-噻吩基基团取代），含有1至5个碳原子的卤代烷基基团，或者与它们连接的氮一起形成2-氧代-1-吡咯烷基基团，A-B表示与连接的氧原子一起的乙烯氧基团，乙炔氧基团，2-氧代-1-氧乙烯基团或2-羟基-1-氧乙烯基团。通式I的化合物具有抗抑郁、抗侵略和多巴胺能性质。
• Chatelus, Annales de Chimie (Cachan, France), 1949, vol. <12> 4, p. 505,526
  作者：Chatelus

  DOI：——

  日期：——