2-iodo-3-methoxy-5-methylbenzoic acid | 133344-02-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-iodo-3-methoxy-5-methylbenzoic acid
• CAS: 133344-02-2
• 化学式: C₉H₉IO₃
• 分子量: 292.073
• InChiKey: ZJGRCWLNFYZFPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  2-iodo-3-methoxy-5-methylbenzoic acid 在 4-二甲氨基吡啶 、 氯化亚砜 、 potassium carbonate 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 27.0h， 生成 4,5-dimethoxy-1-naphthyl 2-iodo-3-methoxy-5-methylbenzoate
  参考文献：
  名称：

  Annulation Strategies for Benzo[b]fluorene Synthesis:  Efficient Routes to the Kinafluorenone and WS-5995 Antibiotics

  摘要：

  Intramolecular palladium-mediated arylation approaches to benzo[b]fluorenes have been investigated. The methodology has been applied in a short synthesis of tri-O-methylkinafluorenone, providing an effective alternative td Friedel-Crafts-based approaches. During the course of this work, an acid-promoted quinolactonization of naphthoquinones was also developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C, and functional analogues was demonstrated, and antitumoral activity of this class was determined.

  DOI：

  10.1021/jo0056186
• 作为产物：
  描述：

  3-甲氧基-5-甲基苯甲酸甲酯 在 sodium hydroxide 、 potassium iodide 、 thallium(III) trifluoroacetate 作用下， 反应 2.0h， 生成 2-iodo-3-methoxy-5-methylbenzoic acid
  参考文献：
  名称：

  吉尔卡星糖苷配基的简明全合成

  摘要：

  据报道，Gilvocarcins M和E（并正式为V）的糖苷配基的简短而趋同的合成涉及关键步骤，即Pd介导的分子内联芳基偶联。

  DOI：

  10.1016/s0040-4039(00)97051-5

文献信息

• A xanthate-based free radical approach to defucogilvocarcin M
  作者：Omar Cortezano-Arellano、Alejandro Cordero-Vargas

  DOI：10.1016/j.tetlet.2009.11.076

  日期：2010.1

  A formal total synthesis of the aglycon of gilvocarcin M is described. The synthesis is based on the construction of the key naphthalene 7 via a free radical addition–cyclization protocol followed by aromatization of the resulting α-tetralone. This highly functionalized aromatic system is coupled to the corresponding acid chloride 6 to afford ester 4, which by treatment with a catalytic amount of palladium

  描述了gilvocarcin M糖苷配基的正式全合成。合成是基于关键的萘7的构建，该结构是通过自由基加成-环化方案，然后对所得的α-四氢萘酮进行芳构化。该高度官能化的芳族体系与相应的酰氯6偶联，得到酯4，该酯4通过用催化量的钯（0）处理而生成的脱烟头叶绿素M（1a）。
• Total Synthesis of the Gilvocarcins
  作者：Takamitsu Hosoya、Eiji Takashiro、Takashi Matsumoto、Keisuke Suzuki

  DOI：10.1021/ja00082a023

  日期：1994.2

  2-methoxyfuran (6). The naphthol derivative 34, selectively synthesized by these two tactics, served as the common intermediate to both 1a and 1b. Acylation of 34 with benzoic acid derivative 39 followed by Pd-catalyzed cyclization gave gilvocarcin M (1a), and a similar synthetic sequence starting with the coupling of 34 with 49 led to the first total synthesis of gilvocarcin V (1b)

  已完成芳基 C-糖苷类抗生素 gilvocarcin M (1a) 和 gilvocarcin V (1b) 的全合成。关键步骤包括 (1) D-fucofuranosyl acetate 27 与碘苯酚 26 的对比偶联，这是通过使用 Cp 2 HfCl 2 -AgClO 4 或相关的有机硅烷衍生试剂实现的，以及 (2) 区域选择性 [4+2] 环加成反应一种含糖的苄基物质，通过在 -78 o C 下用 n-BuLi 和 2-甲氧基呋喃处理邻卤代芳基三氟甲磺酸酯 33-α 生成 (6)。通过这两种策略选择性合成的萘酚衍生物 34 作为 1a 和 1b 的共同中间体。34 与苯甲酸衍生物 39 酰化，然后 Pd 催化环化得到 gilvocarcin M (1a)，
• Regioselective lactonization of naphthoquinones: synthesis and antitumoral activity of the WS-5995 antibiotics
  作者：Ghassan Qabaja、Elisabeth M. Perchellet、Jean-Pierre Perchellet、Graham B Jones

  DOI：10.1016/s0040-4039(00)00329-4

  日期：2000.4

  An acid promoted quinolactonization of naphthoquinones has been developed, providing direct access to either ortho or para isomers as desired. Application of this methodology in syntheses of the antibiotics WS-5995A, WS-5995C and functional analogs is demonstrated. Preliminary antitumoral activity of the analogs is presented together with electrochemical analysis. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Total synthesis and absolute stereochemical assignment of gilvocarcin M.
  作者：Takashi Matsumoto、Takamitsu Hosoya、Keisuke Suzuki

  DOI：10.1021/ja00035a069

  日期：1992.4
• DESHPANDE, PRASHANT P.;MARTIN, OLIVIER R., TETRAHEDRON LETT., 31,(1990) N4, C. 6313-6316
  作者：DESHPANDE, PRASHANT P.、MARTIN, OLIVIER R.

  DOI：——

  日期：——