3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanoic acid | 18123-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanoic acid
• 英文别名: 3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propionic acid；3-(1-tetralone-2yl)propanoic acid；3-(1-oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionic acid；3-(1-Oxo-1,2,3,4-tetrahydro-[2]naphthyl)-propionsaeure；1,2,3,4-tetrahydro-1-oxo-2-naphthalenepropanoic acid；3-(1-oxo-3,4-dihydro-2H-naphthalen-2-yl)propanoic Acid
• CAS: 18123-48-3
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: JZTDPYMLZXRSQP-UHFFFAOYSA-N

物化性质

• 熔点：
  107-108 °C
• 沸点：
  416.0±14.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanoic acid 在 氢氧化钾 、 sodium hydroxide 、 硫酸 、 一水合肼 作用下， 以 甲醇 、 二氯甲烷 、 二乙二醇 为溶剂， 反应 2.0h， 生成 6-(2-羧基-苯基)-己酸
  参考文献：
  名称：

  Ugi,I. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 641, p. 63 - 70

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氧代-1,2,3,4-四氢萘-2-羧酸乙酯 在 sodium hydroxide 、 sodium 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 12.0h， 生成 3-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanoic acid
  参考文献：
  名称：

  Studies of Cerebral Protective Agents. Preparation and Pharmacological Evaluation of 1-(1,4-Benzoquinon-2-yl)-1,2,3,4-tetrahydronaphthalenes as Potent Cerebral Protective Agents.

  摘要：

  为了评估其药理活性，我们合成了两个新的1-(1,4-苯醌-2-基)-1,2,3,4-四氢萘（3,4）系列。这些化合物在大鼠脑匀浆中表现出显著的抗脂质过氧化（ALP）活性，其中一些化合物对小鼠的低氧性缺氧具有保护作用。

  DOI：

  10.1248/cpb.44.132

文献信息

• Electrocatalytic Dehydrogenative Esterification of Aliphatic Carboxylic Acids: Access to Bioactive Lactones
  作者：Sheng Zhang、Fei Lian、Mengyu Xue、Tengteng Qin、Lijun Li、Xu Zhang、Kun Xu

  DOI：10.1021/acs.orglett.7b03333

  日期：2017.12.15

  A scalable and efficient electrocatalytic dehydrogenative esterification is reported. With an indirect electrolysis strategy, both intra- and intermolecular-type reactions were amenable to this practical method. With n-Bu4NI as the catalyst, undesired decarboxylation and Baeyer–Villiger oxidation were suppressed. More importantly, this novel method provided reliable and direct access to the natural

  据报道可扩展且有效的电催化脱氢酯化。通过间接电解策略，分子内和分子间反应都适合该实用方法。使用n -Bu 4 NI作为催化剂，可以抑制不希望的脱羧和Baeyer-Villiger氧化。更重要的是，这种新颖的方法可提供以克为单位的对天然产物胞嘧啶酮A的可靠，直接的获取。
• In Situ Generated (Hypo)Iodite Catalysts for the Direct α-Oxyacylation of Carbonyl Compounds with Carboxylic Acids
  作者：Muhammet Uyanik、Daisuke Suzuki、Takeshi Yasui、Kazuaki Ishihara

  DOI：10.1002/anie.201101522

  日期：2011.5.27

  It′s the iodine: The intra‐ and intermolecular title reaction is catalyzed by an in situ generated ammonium (hypo)iodite species. Either H2O2 or tert‐butyl hydroperoxide (TBHP) can be used as an environmentally benign oxidant and a wide range of substrates react to give the corresponding α‐acyloxycarbonyl compounds in good to excellent yields.

  它是碘：分子内和分子间标题反应是由原位生成的亚碘铵（次同）催化的。H 2 O 2或叔丁基氢过氧化物（TBHP）都可以用作环境友好的氧化剂，并且多种底物反应生成相应的α-酰氧基羰基化合物，收率良好至优异。
• Facile Synthesis of Spirocyclic Lactams from β-Keto Carboxylic Acids
  作者：Wei Yang、Xianyu Sun、Wenbo Yu、Rachita Rai、Jeffrey R. Deschamps、Lauren A. Mitchell、Chao Jiang、Alexander D. MacKerell、Fengtian Xue

  DOI：10.1021/acs.orglett.5b01350

  日期：2015.6.19

  A facile synthesis of spirocyclic lactams starting from β-keto carboxylic acids via a one-pot cascade reaction involving a Curtius rearrangement and an intramolecular nucleophilic addition of the enol carbon to the isocyanate intermediate is reported. The same conditions have also been used for the generation of fused cyclic lactams with similar good yields. The synthetic value of this method has been

  据报道，通过一锅级联反应，从Cu酮重排，并将烯醇碳分子内亲核加成到异氰酸酯中间体上，从β-酮羧酸容易地合成螺环内酰胺。相同的条件也已用于产生具有相似良好收率的稠合环状内酰胺。该方法的合成价值已通过有效合成四环螺内酰胺8和五环螺内酰胺9得以证明。
• Preparation of Cyclic .ALPHA.-Hydroxy Ketones from .DELTA.- and .EPSILON.-Keto Acids Induced by the Generation of a Novel Acyl Anion Equivalent from the Carboxyl Group.
  作者：Hatsuo MAEDA、Haruka ASHIE、Toshihide MAKI、Hidenobu OHMORI

  DOI：10.1248/cpb.45.1729

  日期：——

  An improved method for the transformation of keto acids into cyclic α-hydroxy ketones, induced by the electrochemical generation of a novel acyl anion equivalent from the carboxy group, has been developed. Both five- and six-membered rings were constructed by constant-current electrolysis of δ- and ε-keto acids in the presence of Bu3P using an undivided cell equipped with a graphite anode and a Pt cathode. Attempts to prepare four- and seven-membered ring carbocycles were unsuccessful. The electrochemical reaction was found to be highly stereoselective when cyclization took place onto cyclopentanone and substituted cyclohexanone rings. Stereochemical aspects of the formation of bicyclic products, especially those having a bicyclo[4.3.0]skeleton, are discussed.

  开发了一种改进的方法，通过电化学生成从羧基衍生出的新型酰基阴离子等价物，诱导将酮酸转化为环状α-羟基酮。通过在配有石墨阳极和铂阴极的无隔膜电池中，在Bu3P存在下对δ-和ε-酮酸进行恒流电解，构建了五元和六元环。尝试制备四元和七元环碳环未能成功。当环化反应发生在环戊酮和取代环己酮环上时，发现该电化学反应具有高度立体选择性。讨论了双环产物形成的立体化学方面，特别是具有双环[4.3.0]骨架的产物。
• Construction of Fused Cyclooctanoid Ring Systems via Seven-Membered Ring Carbonyl Ylides
  作者：Sengodagounder Muthusamy、Srinivasarao Arulananda Babu、Chidambaram Gunanathan、Eringathodi Suresh、Parthasarathi Dastidar

  DOI：10.1246/bcsj.75.801

  日期：2002.4

  A series of α-diazo carbonyl compounds tethered to cyclopentanone/cyclohexanone/1-tetralone units have been synthesized using a diazomethane solution to construct various fused cyclooctane ring systems via rhodium-generated carbonyl ylides. The reaction of rhodium(II) acetate dimer with various α-diazo carbonyl compounds generated transient cyclic seven-membered ring carbonyl ylides, which underwent facile 1,3-dipolar cycloadditions with dipolarophiles, like N-phenylmaleimide, p-benzoquinone, and DMAD to furnish a variety of fused epoxy-bridged cyclooctane ring systems in a tandem manner. Interestingly, an oxepine ring system was generated via an intramolecular proton transfer of a seven-membered ring carbonyl ylide. A tri-oxa polycyclic compound was obtained in the case of p-benzoquinone as dipolarophile. A single-crystal X-ray analysis of a fused cyclootanoid derivative is reported to decisively establish the structure and stereochemistry of the fused epoxy-bridged cyclooctane ring systems; a further analysis revealed the existence of a unique intermolecular C–H···π interaction motif in the solid-state architecture.

  一系列连接到环戊酮/环己酮/1-四氢萘酮单元的α-重氮羰基化合物通过使用重氮甲烷溶液，通过铑产生的羰基叶立德构建了各种融合的环辛烷环体系。铑(II)醋酸二聚体与各种α-重氮羰基化合物的反应生成了瞬态的七元环羰基叶立德，这些叶立德与亲二极体如N-苯基马来酰亚胺、对苯醌和DMAD进行了方便的1,3-偶极环加成反应，以串联方式提供了多种融合的环氧桥接环辛烷环体系。有趣的是，通过七元环羰基叶立德的分子内质子转移生成了一个oxepine环体系。当对苯醌作为亲二极体时，得到了一个三氧杂多环化合物。报道了对融合环辛烷类衍生物的单晶X射线分析，以明确确定融合环氧桥接环辛烷环体系的结构和立体化学；进一步分析揭示了固态结构中存在的独特分子间C-H···π相互作用模式。