3-甲基-4-氧-4,5,6,7-四氢-1氢-吲哚-2-甲酸乙酯 | 7272-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 3-甲基-4-氧-4,5,6,7-四氢-1氢-吲哚-2-甲酸乙酯
• 中文别名: 4,5,6,7-四氢-3-甲基-4-氧吲哚-2-羧酸乙酯
• 英文名称: ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carboxylate
• 英文别名: ethyl 3-methyl-4-oxo-4,5,6-tetrahydro-1H-indole-2-carboxylate；ethyl 3-methyl-4-oxo-4,5,6,7-tetrahydroindole-2-carboxylate；2-carbethoxy-3-methyl-4-oxo-4,5,6,7-tetrahydroindole；3-methyl-4-oxo-4,5,6,7-tetrahydro-indole-2-carboxylic acid ethyl ester；4,5,6,7-Tetrahydro-3-methyl-4-oxo-indole-2-carboxylic-acid-ethylester；2-Carbethoxy-3-methyl-4-keto-4,5,6,7-tetrahydro-indol；ethyl 3-methyl-4-oxo-1,5,6,7-tetrahydroindole-2-carboxylate
• CAS: 7272-58-4
• 化学式: C₁₂H₁₅NO₃
• mdl: MFCD00715541
• 分子量: 221.256
• InChiKey: VQLLFMATRGJDCH-UHFFFAOYSA-N

物化性质

• 熔点：
  165-167 °C(Solv: ethanol (64-17-5))
• 沸点：
  428.2±45.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲基-4-氧-4,5,6,7-四氢-1氢-吲哚-2-甲酸乙酯 生成 乙基1,3-二甲基-4-羰基-4,5,6,7-四氢-1H-吲哚-2-羧酸酯
  参考文献：
  名称：

  BARDAKOS V.; SUCROW W., CHEM. BER., 1978, 111, NO 5, 1780-1788,

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(二甲基氨基)环己-2-烯-1-酮 、 2-(羟亚氨基)乙酰乙酸乙酯 在 sodium acetate 、 锌 作用下， 以 溶剂黄146 为溶剂， 以35%的产率得到3-甲基-4-氧-4,5,6,7-四氢-1氢-吲哚-2-甲酸乙酯
  参考文献：
  名称：

  SYNTHESIS OF ETHYL PYRROLE-2-CARBOXYLATES: A REGIOSELECTIVE CYCLIZATION OF ENAMINONES UNDER KNORR-TYPE CONDITIONS

  摘要：

  A regioselective formation of ethyl pyrrole-2-carboxylates 4 and 5 is effected by reductive condensation of enaminones 1a-f and ethyl 2-oximinoacetoacetate 2. The structures of the products have been delineated by spectroscopic methods.

  DOI：

  10.1081/scc-120002701

文献信息

• Chemical compounds
  申请人：Astrazeneca UK Limited

  公开号：US06291507B1

  公开（公告）日：2001-09-18

  A pharmaceutical composition which comprises a compound of formula (I) or a pharmaceutically acceptable salt, ester or amide thereof, which is an inhibitor of monocyte chemoattractant protein-1, and wherein A and B form an optionally substituted alkylene chain so as to form a ring with the carbon atoms to which they are attached; X is CH2 or SO2, R1 is an optionally substituted aryl or heteroaryl ring; R2 is a specified organic group such as carboxy, and R3 is hydrogen or a specified organic group; in combination with a pharmaceutically acceptable carrier. Certain compounds of formula (I) are novel and are claimed as such.

  一种制药组合物，包括式（I）的化合物或其药用盐、酯或酰胺，该化合物是单核细胞趋化蛋白-1的抑制剂，其中A和B形成一个可选择取代的烷基链，以形成与它们连接的碳原子形成环；X为CH2或SO2，R1为可选择取代的芳基或杂环芳基环；R2为指定的有机基团，如羧基，R3为氢或指定的有机基团；与药用可接受载体结合。式（I）的某些化合物是新颖的并据此声明。
• Thiopyrano[2,3-e]indol-2-ones: Angelicin heteroanalogues with potent photoantiproliferative activity
  作者：Paola Barraja、Patrizia Diana、Alessandra Montalbano、Anna Carbone、Girolamo Cirrincione、Giampietro Viola、Alessia Salvador、Daniela Vedaldi、Francesco Dall’Acqua

  DOI：10.1016/j.bmc.2008.10.002

  日期：2008.11

  A new class of compounds, the thiopyrano[2,3-e]indol-2-ones, bioisosters of the angular furocoumarin angelicin, was synthesized with the aim of obtaining new photochemotherapeutic agents. In particular 7,8-dimethyl-thiopyranoindolone 6c s showed a remarkable phototoxicity and a great dose UVA dependence reaching IC(50) values at submicromolar level. This latter photoinduced a massive apoptosis and

  为了获得新的光化学治疗剂，合成了一类新的化合物，即角呋喃香豆素当归的生物等位基因thiopyrano [2,3-e] indol-2-ones。特别是7,8-二甲基-硫代吡喃并吲哚酮6c s表现出了显着的光毒性，并且在亚微摩尔水平上对UVA的依赖性很大，达到了IC（50）值。后者光诱导大量的细胞凋亡，并对脂质和蛋白质产生显着的光损伤。尽管它不插入DNA，但它能够引起DNA碱基的光氧化。
• Porphyrins with exocyclic rings. 1. Chemistry of 4,5,6,7-tetrahydro-1H-indoles: synthesis of acetoxy derivatives, dihydroindoles, and novel porphyrins with four exocyclic rings
  作者：Timothy D. Lash、Karla A. Bladel、Craig M. Shiner、Donna L. Zajeski、Rajiv P. Balasubramaniam

  DOI：10.1021/jo00044a012

  日期：1992.8

  A variety of 4,5,6,7-tetrahydro-1H-indoles (THI's) and 4-oxo-4,5,6,7-tetrahydro-1H-indoles (4-oxoTHIs) have been synthesized from cyclohexanone and 1,3-cyclohexanedione, respectively. The THI's reacted regioselectively with lead tetraacetate in acetic acid to give the 7-acetoxy derivatives. The isomeric 4-acetoxyTHI's were prepared by first reducing the corresponding 4-oxoTHI's with sodium borohydride and then reacting the resulting hydroxyTHI' s with acetic acid-pyridine. Both series of acetoxyTHI's underwent elimination of acetic acid when heated with pyridine-acetic anhydride to give dihydroindoles. The 7-acetoxyTHI's were hydrolyzed with potassium hydroxide in methanol-water and carefully neutralized with hydrochloric acid to give the corresponding hydroxyTHI carboxylic acids. Treatment with potassium ferricyanide in refluxing acetic acid gave good yields of tetrapropanoporphyrins when 3-methyl-, 3-ethyl-, or 3-n-propyl substituents were present. The 3-phenylTHI gave variable yields of the corresponding tetraphenylporphyrin. The 3-isopropylTHI gave only trace amounts of porphyrin under these conditions, and the 3-tert-butylTHI failed to give any porphyrin product. THI's with 6-methyl or 6,6-dimethyl substituents were prepared in two steps from 5-methyl-1,3-cyclohexanedione or dimedone, respectively. These compounds also reacted smoothly with lead tetraacetate to give the 7-acetoxy derivatives in high yield. Attempts to convert the 6,6-dimethylTHI's into symmetrical porphyrins were unsuccessful, although the 6-methylTHI gave a mixture of porphyrin stereoisomers in low yield. The influence of alkyl substituents and carbocyclic rings on the cyclotetramerization of THI's is discussed.
• Clezy, Peter S.; Prashar, Jognandan K., Australian Journal of Chemistry, 1990, vol. 43, # 5, p. 825 - 837
  作者：Clezy, Peter S.、Prashar, Jognandan K.

  DOI：——

  日期：——
• The Intramolecular Photometathesis of Pyrroles
  作者：Luke D. Elliott、Malcolm Berry、Andrew J. Orr-Ewing、Kevin I. Booker-Milburn

  DOI：10.1021/ja070254l

  日期：2007.3.1

  UV irradiation of various electron deficient pyrrole derivatives induces a novel methathesis sequence resulting in selective cleavage of the 2,3-pyrrole bond. The overall sequence has been shown to proceed by two discrete wavelength-dependent steps involving sequential [2+2] cyclobutane formation followed by photochemically mediated retro-[2+2] to the products.