2-碘-3,4,5-三甲氧基苯甲酸 | 98799-41-8

• 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-碘-3,4,5-三甲氧基苯甲酸
• 英文名称: 2-iodo-3,4,5-trimethoxybenzoic acid
• 英文别名: Benzoic acid, 2-iodo-3,4,5-trimethoxy-
• CAS: 98799-41-8
• 化学式: C₁₀H₁₁IO₅
• 分子量: 338.099
• InChiKey: HCOQESVRKVCVKG-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  394.0±42.0 °C(Predicted)
• 密度：
  1.724±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-碘-3,4,5-三甲氧基苯甲酸 在 氯化亚砜 、 铜 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 3,4,5-trimethoxy-9,17,23,25-tetraoxapentacyclo[17.7.0.02,7.010,15.022,26]hexacosa-1(19),2,4,6,10,12,14,20,22(26)-nonaene-8,18-dione
  参考文献：
  名称：

  Takahashi, Masami; Ogiku, Tsuyosi; Okamura, Kimio, Journal of the Chemical Society. Perkin transactions I, 1993, # 13, p. 1473 - 1480

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸甲酯 在 碘 、 sodium carbonate 作用下， 生成 2-碘-3,4,5-三甲氧基苯甲酸
  参考文献：
  名称：

  Trivedi, K. K.; Kochak, Geeta; Misra, K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 9, p. 925 - 926

  摘要：

  DOI：

文献信息

• Total Synthesis of (+)-Isoschizandrin Utilizing a Samarium(II) Iodide-Promoted 8-Endo Ketyl−Olefin Cyclization
  作者：Gary A. Molander、Kelly M. George、Lauren G. Monovich

  DOI：10.1021/jo0347361

  日期：2003.12.1

  The 13-step synthesis of (+)-isoschizandrin reported herein features a samarium(II) iodide-promoted 8-endo ketyl-olefin coupling to assemble the eight-membered ring present in the target concomitantly with the required functionality and stereochemistry. In constructing (+)-isoschizandrin as a single atropisomer, the synthesis utilizes a kinetic resolution of a seven-membered lactone using a CBS-oxazaborolidine

  本文报道的（+）-异五味子素的13个步骤的合成具有碘化sa（II）促进的8-内基酮基-烯烃偶联，以组装存在于靶中的八元环以及所需的功能性和立体化学。在构建作为单一阻转异构体的（+）-异五味子素中，合成过程利用CBS-恶唑硼烷定律利用了七元内酯的动力学拆分。
• Intramolecular biaryl coupling reaction of benzyl benzoate and phenyl benzoate derivatives, and its application to the formal synthesis of (−)-steganone
  作者：Shigemitsu Takeda、Hitoshi Abe、Yasuo Takeuchi、Takashi Harayama

  DOI：10.1016/j.tet.2006.10.059

  日期：2007.1

  Construction of the biaryl moiety of stegane and related compounds through an intramolecular biaryl coupling reaction is described. Undesired products were obtained by the intramolecular coupling reaction of benzyl benzoates (8, 13, and 14) because of their steric and electrostatic properties, and only that of phenyl benzoates (26b and 26c) afforded the desired biaryl lactones in good yields. An asymmetric

  描述了通过分子内联芳基偶合反应构建硬脂烷和相关化合物的联芳基部分。不希望的产物通过苄基苯甲酸酯（的分子内偶合反应得到8，13，和14，因为它们的空间和静电性质），并且只有苯基苯甲酸酯（的26B和26C，得到所需的二芳基内酯以良好产率）。使用对映选择性内酯开放反应，然后四步转化为已知化合物，已经实现了标题化合物的不对称形式合成。
• Synthesis of All-Methylated Isorugosin B
  作者：Kazuma Shioe、Yasuo Takeuchi、Takashi Harayama、Hitoshi Abe

  DOI：10.1248/cpb.58.435

  日期：——

  All-methylated isorugosin B was synthesized via two-step esterification between optically active valoneic acid and glucose derivatives.

  全甲基化异龙胆素 B 是通过光学活性丙酮酸和葡萄糖衍生物之间的两步酯化反应合成的。
• Studies Relevant to Ellagitannin Chemistry:  Highly Diastereoselective Intramolecular Biaryl Coupling in Bis(iodotrimethoxybenzoyl) Hexopyranose Derivatives
  作者：Dongcheng Dai、Olivier R. Martin

  DOI：10.1021/jo971722k

  日期：1998.10.1

  Internal biaryl coupling reactions of carbohydrate derivatives carrying two 2-iodo-3,4,5-trimethoxybenzoyl groups under Ullmann conditions were investigated. With substituents at positions 2,3 or 4,6 of a D-glucopyranoside, 2,3 of a D-mannopyranoside, and 3,4 of a D-galactopyranoside, the coupling was found to proceed with a very high degree of stereoselectivity, leading exclusively to the (S)-epimer of the resulting hexamethoxydiphenoyl residue from the D-gluco and D-galacto substrates, and to the (R)-epimer from the D-manno substrate. With substituents at positions 2,4 of D-glucopyranose derivatives in the C-1(4) conformation and at positions 5,6 of a D-glucofuranose derivative, the coupling proceeded efficiently but with modest stereoselectivity. Some deiodinated starting material was formed as a byproduct in all reactions. These results are relevant to ellagitannin chemistry in that they provide further understanding of the structural requirements for highly diastereoselective biaryl coupling within carbohydrate units. In addition, the efficient, complementary reactions of the D-manno and D-galacto substrates provide a method for the enantioselective synthesis of hexamethoxydiphenoic acid derivatives.
• Studies in SRN1 series. Part 14. Direct synthesis of benzo[c]phenanthridines and benzo[c]phenanthridones via SRN1 reactions
  作者：Rene Beugelmans、Jacqueline Chastanet、Helene Ginsburg、Leticia Quintero-Cortes、Georges Roussi

  DOI：10.1021/jo00224a057

  日期：1985.11