2,3-二甲氧基-5-碘苯甲酸 | 134419-42-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,3-二甲氧基-5-碘苯甲酸
• 英文名称: 2,3-dimethoxy-5-iodobenzoic acid
• 英文别名: 5-iodo-2,3-dimethoxybenzoic acid
• CAS: 134419-42-4
• 化学式: C₉H₉IO₄
• 分子量: 308.073
• InChiKey: CDTUOGIMRVPSJG-UHFFFAOYSA-N

物化性质

• 沸点：
  388.0±42.0 °C(Predicted)
• 密度：
  1.790±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二甲氧基-5-碘苯甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以100%的产率得到5-iodo-2,3-dimethoxybenzoyl chloride
  参考文献：
  名称：

  Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide and its 5-halogen-2-alkoxyl homologues

  摘要：

  (S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [I-125]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [I-125]-MIZAC at 1800 Ci/mmol. Binding of [I-125]-MIZAC in rat entorhinal cortex revealed a K-D of 1.37 +/- 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [I-125]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [I-125]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.

  DOI：

  10.1016/s0223-5234(97)81676-5
• 作为产物：
  描述：

  5-溴-2,3-二甲氧基苯甲酸甲酯 在 吡啶 、 sodium hydroxide 、 氯化亚砜 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 、 水 、 苯 为溶剂， 生成 2,3-二甲氧基-5-碘苯甲酸
  参考文献：
  名称：

  Mach, Robert H.; Hammond, Philip S.; Huang, Yunsheng, Medicinal Chemistry Research, 1999, vol. 9, # 6, p. 355 - 373

  摘要：

  DOI：

文献信息

• Asymmetric dearomative spirolactonization of naphthols using λ3-iodanes under chiral phase-transfer catalysis
  作者：Kevin Antien、Guillaume Viault、Laurent Pouységu、Philippe A. Peixoto、Stéphane Quideau

  DOI：10.1016/j.tet.2017.04.028

  日期：2017.6

  The asymmetric phase-transfer catalytic effect of chiral Cinchona alkaloid-derived quaternary ammonium salts was investigated in the context of the λ3-iodane-mediated dearomative spirolactonization of naphthols. The scope and limitations of this methodology were evaluated using various substrates, which were converted into spirolactones in good yields and with enantiomeric excesses up to 58%.

  手性的不对称相转移催化效果金鸡纳生物碱类季铵盐在λ的情况下进行了研究3萘酚的-iodane介导dearomative spirolactonization。使用各种底物评估了该方法的范围和局限性，这些底物以良好的产率转化为螺内酯，对映体过量最高可达58％。
• In vitro affinities of various halogenated benzamide derivatives as potential radioligands for non-invasive quantification of D2-like dopamine receptors
  作者：Daniela Stark、Markus Piel、Harald Hübner、Peter Gmeiner、Gerhard Gründer、Frank Rösch

  DOI：10.1016/j.bmc.2007.07.017

  日期：2007.11

  Benzamide derivatives as radiotracers have played an important role in diagnosing malfunction in dopaminergic neurotransmission. A variety of halogenated and two unsubstituted benzamide derivatives were synthesised and their in vitro affinities to dopaminergic, serotonergic and adrenergic receptors and their lipophilicities were determined. As references IBZM (3), raclopride (4) and FLB457 (5) were tested as well. The two iodinated compounds NAE (27) and NADE (28) displayed K-i values of 0.68 and 14 nM for the D-2 receptor. The well-established radiotracers FP (1) and DMFP (2) showed affinities in the same range as did the brominated compounds NABrE (29) and NABrDE (30). The logD(7.4) values of 2.91 for NAE (27) and of 2.81 for NADE (28) are in the range of those found for IBZM (3), FP (1) and DMFP (2). These facts allow to expect good properties for the two iodinated compounds NAE (27) and NADE (28) regarding in vivo imaging with SPECT. (C) 2007 Elsevier Ltd. All rights reserved.
• Langer; Dolle; Halldin, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S366-S368
  作者：Langer、Dolle、Halldin、Demphel、Vaufrey、Nagren、Lundkvist、Sandell、Crouzel

  DOI：——

  日期：——
• Fluorinated and iodinated dopamine agents: D2 imaging agents for PET and SPECT
  作者：S. Chumpradit、M. P. Kung、J. Billings、R. Mach、H. F. Kung

  DOI：10.1021/jm00054a005

  日期：1993.1

  A novel series of dual-labeling D2 dopamine agents (labeled with either F-18 or I-123 for PET or SPECT imaging, respectively) was investigated. Two desired fluorinated and iodinated dopamine agents, FIDA1, (S)-(-)-2-(2-fluoroethoxy)-5-iodo-3-methoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide, and FIDA2, (R)-(+)-2,3-dimethoxy-5-iodo-N-[(1-(4'-fluorobenzyl)-2-pyrrolidinyl)methyl]benzamide, were synthesized. Both compounds displayed high affinity to the D2 receptor of rat striatal membrane preparations (K(d) = 0.13 and 0.02 nM for FIDA1 and FIDA2, respectively). The biodistribution study in rats exhibited high localization in the striata of the brain with the striatum/cerebellum ratio reaching 29.3 and 13.1 at 1 h post iv injection for FIDA1 and FIDA2, respectively. Imaging studies with [F-18]- and [I-123]FIDA2 in monkeys, with PET and SPECT, respectively, showed comparable high selective striatal uptake. These results suggest that they are potentially useful D2 dopamine receptor imaging agents for PET and SPECT.
• New Short Synthesis of (5)‐2,3‐Dimethoxy‐N‐[(1‐ethyl‐2‐pyrrolidinyl)methyl]‐5‐iodobenzamide: Dopamine D2 Receptor
  作者：Alummoottil V. Joshua、Sanjay K. Sharma、Douglas N. Abrams

  DOI：10.1080/00397910701771199

  日期：2008.1.1

  A new short and highly efficient synthesis of (5)-2,3-dimethoxy-N[(1-ethyl-2pyrrolidinyl)methyl]-5-iodobenzamide (epidepride, 1) from 3-methoxy-salicylaldehyde (o-vanillin, 2) and 3-methoxysalicyclic acid (6) was achieved by employing a new iodination method with iodine monochloride and iodine nitrate under basic conditions.