2-(2-氧代四氢呋喃-3-基)-1H-异吲哚-1,3(2H)-二酮 | 42473-02-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(2-氧代四氢呋喃-3-基)-1H-异吲哚-1,3(2H)-二酮
• 英文名称: 2-(2-oxotetrahydrofuran-3-yl)isoindolin-1,3-dione
• 英文别名: α-phthalimido-γ-butyrolactone；2-phthalimido-4-butyrolactone；N-(2-oxo-tetrahydro-furan-3-yl)-phthalimide；N,N-phthaloyl-homoserine lactone；N,N-Phthaloyl-homoserin-lacton；L-α-phthalimido-γ-butyrolactone；2-(2-oxotetrahydrofuran-3-yl)-1H-isoindole-1,3(2H)-dione；2-(2-oxooxolan-3-yl)isoindole-1,3-dione
• CAS: 42473-02-9
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: HPJABVAESJDAES-UHFFFAOYSA-N

物化性质

• 熔点：
  176-178 °C
• 沸点：
  448.7±38.0 °C(Predicted)
• 密度：
  1.516±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(2-氧代四氢呋喃-3-基)-1H-异吲哚-1,3(2H)-二酮 在 六甲基磷酰三胺 、 N-氯代丁二酰亚胺 、 硫酸 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 58.0h， 生成 methyl (S)-4-oxo-2-phthalimidobutanoate
  参考文献：
  名称：

  A new class of unusual α-aminoacids : α-aminoacid β,γ-enol thioethers

  摘要：

  Two representative alpha-aminoacid beta,gamma-enol thioethers have been synthesized starting from the corresponding easily available saturated alpha-aminoacids by a Pummerer-like reaction.

  DOI：

  10.1016/s0040-4039(00)92290-1
• 作为产物：
  描述：

  α-溴-γ-丁内酯 、 potassium phtalimide 在 N,N-二甲基甲酰胺 作用下， 生成 2-(2-氧代四氢呋喃-3-基)-1H-异吲哚-1,3(2H)-二酮
  参考文献：
  名称：

  SYNTHESIS OF 4-AMINOBUTYRIC ACID AND 2,4-DIAMINOBUTYRIC ACID FROM BUTYROLACTONE

  摘要：

  γ-丁内酯与1摩尔邻苯二甲酰亚胺钾的环开合反应，以及中间产物的水解，产生了4-氨基丁酸，收率极高。1摩尔邻苯二甲酰亚胺钾与2-溴-4-丁内酯的缩合反应产生了2-邻苯二甲酰亚胺内酯，也可以通过处理第二分子邻苯二甲酰亚胺钾来开启。这种二邻苯二甲酰亚胺酸在水解后，以极高的收率产生了2,4-二氨基丁酸二盐酸盐。

  DOI：

  10.1139/v58-084

文献信息

• Substituted phenylacetic acid compounds and process for preparation
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US04237305A1

  公开（公告）日：1980-12-02

  Substituted phenylacetic acid compounds represented by the following general formula and preparation thereof: ##STR1## wherein R.sup.1 is hydrogen or protected carboxy, R.sup.2 is hydrogen, or protected amino, provided that when R.sup.1 is hydrogen, then R.sup.2 is protected amino, and when R.sup.2 is hydrogen, then R.sup.1 is protected carboxy, R.sup.3 is oxo, hydroxyimino or protected hydroxyimino, R.sup.4 is hydrogen or halogen, and m is an integer of 1 to 3.

  代表以下通式并涉及其制备的取代苯乙酸化合物： ##STR1## 其中R1是氢或保护的羧基，R2是氢或保护的氨基，条件是当R1是氢时，则R2是保护的氨基，而当R2是氢时，则R1是保护的羧基，R3是氧代、羟基亚氨基或保护的羟基亚氨基，R4是氢或卤素，且m是1至3的整数。
• Synthesis of D,L-[2-15N,5-13C]glutamic acid
  作者：John C. Laiuppa、David M. Lemaster

  DOI：10.1002/jlcr.2580331005

  日期：1993.10

  A one-pot procedure is described for the synthesis of D,L-[2-15N,5-13C]glutamic acid from 2-bromo-4–butyrolactone utilizing potassium 15N-phthalimide and potassium 13C-cyanide as label sources. Following a two column purification procedure, the final product is obtained in 38% yield based on the equimolar label sources.

  以 15N-phthalimide 钾和 13C-cyanide 钾为标记源，描述了从 2-bromo-4-butyrolactone 合成 D,L-[2-15N,5-13C]谷氨酸的一步法过程。经过两柱纯化程序，以等摩尔标记源为基础，最终产品的收率为 38%。
• 2-Amino-4-Phosphonyl-butanoate derivates and preparation of 2-amino-4-phosphinyl butanoic acids
  申请人：Monsanto Company

  公开号：EP0265412A2

  公开（公告）日：1988-04-27

  Phosphinylbutanoic acids, such as phosphino­thricin, can be prepared by reacting racemic 4-halo-2-­phthalimidobutyrates with a tricoordinate phosphorus compound represented by the formula:     R¹ - P - (R²)₂ wherein R¹ is methyl or ethyl, and R² is selected from the group consisting of alkoxy having from one to six carbon atoms, aryloxy, and trialkylsilyloxy groups having from one to twelve carbon atoms, to form an intermediate compound; and hydrolyzing the intermediate compound to form the phosphinylbutanoic acids.

  外消旋 4-卤代-2-邻苯二甲酰亚胺丁酸与三配位磷化合物反应，可制备膦酰基丁酸，如膦酰三嗪： R¹ - P - (R²)₂ 其中 R¹ 为甲基或乙基，R² 选自具有 1 至 6 个碳原子的烷氧基、芳氧基和具有 1 至 12 个碳原子的三烷基硅氧基所组成的组，形成中间化合物；水解中间化合物形成膦酰丁酸。
• Search for anticonvulsant and analgesic active derivatives of dihydrofuran-2(3H)-one
  作者：Krzysztof Więckowski、Kinga Sałat、Justyna Bytnar、Marek Bajda、Barbara Filipek、James P. Stables、Barbara Malawska

  DOI：10.1016/j.bmc.2012.08.037

  日期：2012.11

  A series of derivatives of dihydrofuran-2(3H)-one (gamma-butyrolactone, GBL) was synthesized and tested for anticonvulsant, neurotoxic and analgesic activity. In the anticonvulsant screening 10 lactones were effective in the maximal electroshock test (MES) at the highest doses (300 and 100 mg/kg, 0.5 h, ip, mice). Statistical analysis showed correlation between the anticonvulsant activity and relative lipophilicity parameters determined by experimental and computational methods (R-M0, ClogP and M log P). Preliminary antinociceptive evaluation of selected derivatives revealed strong analgesic activity. The majority of the tested compounds showed high efficacy in animal models of acute pain (hot plate and writhing tests) and strong local anesthetic activity (modified tail immersion test). The obtained ED50 values were comparable with such analgesics as acetylsalicylic acid and morphine. (C) 2012 Elsevier Ltd. All rights reserved.
• Krief, A.; Trabelsi, M., Synthetic Communications, 1989, vol. 19, # 7,8, p. 1203 - 1210
  作者：Krief, A.、Trabelsi, M.

  DOI：——

  日期：——

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