3,5-bis(hydroxymethyl)benzoic acid | 123065-60-1

• 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: 3,5-bis(hydroxymethyl)benzoic acid
• 英文别名: 3,5-bis(hydroxylmethyl)benzoic acid
• CAS: 123065-60-1
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: DOHMTKLMXUAOPD-UHFFFAOYSA-N

物化性质

• 熔点：
  112-115 °C
• 沸点：
  452.3±45.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-bis(hydroxymethyl)benzoic acid 在 三溴化磷 作用下， 反应 16.0h， 生成 5-methoxycarbonyl-m-xylylene bisphosphonic acid tetramethyl ester
  参考文献：
  名称：

  Synthesis of 3,5-bis(phosphonomethyl)benzoic acid and its application as a metal oxide surface bivalent anchor

  摘要：

  A protected form of 3,5-bis(phosphonomethyl)benzoic acid (Bpb-OH), a metal oxide surface bivalent anchor, has been synthesized, coupled to an amine functionality, deprotected, and shown to bind to metal oxide surfaces. The protected anchor, 3,5-bis(dimethoxyphosphinylmethyl)benzoic acid (Me(4)Bpb-OH) was synthesized in 23% yield over four steps, coupled to a proline-chromophore, deprotected with a solution of iodotrimethylsilane (TMSI) in acetonitrile and adsorbed to Tin(IV)-doped indium oxide and nanocrystalline TiO2 electodes at surface coverages of 1.5 x 10(-10) mol cm(-2) and 4.9 x 10(-11) mol cm(-2), respectively. Finally, Me(4)Bpb-OH was converted to an amino derivative by attaching a diamino butane linker. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00062-9
• 作为产物：
  描述：

  5-methoxycarbonyl-benzene-1,3-dicarboxylic acid 在 硼烷二甲硫醚络合物 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 3,5-bis(hydroxymethyl)benzoic acid
  参考文献：
  名称：

  A Cysteine‐Directed Proximity‐Driven Crosslinking Method for Native Peptide Bicyclization

  摘要：

  摘要 对原生肽和蛋白质进行高效和位点特异性修饰是合成抗体-药物共轭物以及利用噬菌体展示等基因编码平台构建化学修饰肽库所需要的。特别是，由于多环肽作为治疗药物的吸引力，人们对原生肽的高效多环化非常感兴趣。然而，多环肽合成的传统方法需要正交保护基团或非蛋白源可点击处理。在此，我们报告了一种半胱氨酸引导的接近驱动策略，用于从简单的天然肽前体构建双环肽。这种从线性到双环的转变始于快速的半胱氨酸标记，然后引发近似驱动的胺选择性环化。这种双环化作用在生理条件下迅速进行，产生具有 Cys-Lys-Cys、Lys-Cys-Lys 或 N-terminus-Cys-Cys 缝合模式的双环肽。我们通过构建与蛋白质和 M13 噬菌体融合的双环肽，证明了这一策略的实用性和强大功能，为噬菌体展示新型双环肽库铺平了道路。

  DOI：

  10.1002/anie.202306813

文献信息

• NOVEL GLUCOKINASE ACTIVATORS AND METHODS OF USING SAME
  申请人：Ryono Denis E.

  公开号：US20080009465A1

  公开（公告）日：2008-01-10

  Compounds are provided which are phosphonate and phosphinate activators and thus are useful in treating diabetes and related diseases and have the structure wherein is a heteroaryl ring; R 4 is —(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 ), —(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g , —(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g , —(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10 ), or —(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10 ); R 5 and R 6 are independently selected from H, alkyl and halogen; Y is R 7 (CH 2 ) s or is absent; and X, n, Z, m, R 4 , R 5 , R 6 , R 7 , and s are as defined herein; or a pharmaceutically acceptable salt thereof. A method for treating diabetes and related diseases employing the above compounds is also provided.

  提供了磷酸酯和磷酸酯激活剂，因此在治疗糖尿病和相关疾病方面非常有用，并具有以下结构： 其中 是杂环芳基环； R 4 为—(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 )、—(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g 、—(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g 、—(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10) 或—(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10) ； R 5 和R 6 分别选择自H、烷基和卤素； Y为R 7 (CH 2 ) s 或不存在；以及 X、n、Z、m、R 4 、R 5 、R 6 、R 7 和s如本文所定义；或其药用盐。 还提供了一种利用上述化合物治疗糖尿病和相关疾病的方法。
• Synthesis of Monodisperse Macromolecular Bicyclic and dendritic compounds from (R)-3-hydroxybutanoic acid and benzene-1,3,5-tricarboxylic acid and analysis by fragmenting MALDI-TOF mass spectroscopy
  作者：Dieter Seebach、Guide F. Herrmann、Urs D. Lengweiler、Walter Amrein

  DOI：10.1002/hlca.19970800402

  日期：1997.6.30

  elemental analysis. Especially important is the analysis by mass spectrometry with the MALDI-TOF technique (Fig. 2), proving that the products are monodisperse; application of a new variation of this MS method (post source decay = PSD or fragment analysis by structural time of flight = FASTTM) allows for the observation of metastable fragment ions and, thus, is a tool for structural oligomer analysis (Fig

  如前所示，低聚和聚（β-羟基链烷酸酯）很容易形成具有ca的层状微晶。50-Å的厚度，对应于16个单元的链长（图1）。具有单分散的模型化合物，我们现在已经制备双环衍生物与三个平行（27 - 29）或两个平行和反平行链（68 - 70）由最多至16 3-羟基丁酸（3-HB）单元。我们还制备树枝状化合物（71 - 75，82 - 85）含有不可能被布置为在低聚（3-HB）链薄片; 支链单元由均苯三酸（＝苯-1,3,5-三羧酸）制备。到目前为止，没有一个准备好的样品能够形成晶体或包含适合单晶或粉末衍射X射线分析的晶畴。的末端脱保护的树枝状聚合物（74，75，和85）是多阴离子（最多12个CO 2 H基团）和可生物降解的。通过IR，1 H-和13 C-NMR，[α] D和元素分析已充分表征了大分子HB衍生物（分子量高达10150 Da）。尤其重要的是使用MALDI-TOF技术进行的质谱分析（图2），
• New water-soluble polyanionic dendrimers—phosphoric and 1,3,5-benzenetricarboxylic acid derivatives
  作者：Grzegorz M. Salamończyk

  DOI：10.1016/j.tet.2012.09.094

  日期：2012.12

  Simple, very efficient, and having some aspects of generality, synthesis of water-soluble, polyanionic dendrimeric polyesters with different size, polarity, and flexibility is described. These macromolecular compounds consisting of phosphate or thiophosphate ester units and 1,3,5-benzenetricarboxylic acid building blocks may find potential applications as pharmaceutical agents. Synthesized the title

  描述了简单，非常有效并且具有一般性的一些方面，其具有不同尺寸，极性和挠性的水溶性聚阴离子树枝状聚酯的合成。这些由磷酸酯或硫代磷酸酯单元和1,3,5-苯三羧酸结构单元组成的大分子化合物可能会作为药物使用。合成的标题聚阴离子树状聚合物在表面具有带电的羧基官能团，并以高收率从先前制备的一系列新的磷基树状多元醇中获得。该项目中使用的关键单体是1,3,5-苯三甲酸二苄酯和1,3,5-苯三甲酸双（4-甲氧基苄基）酯。两者都作为树枝状聚阴离子表面的基本前体。
• Nitric oxide enhancing diuretic compounds, compositions and methods of use
  申请人：Garvey S. David

  公开号：US20060189603A1

  公开（公告）日：2006-08-24

  The invention describes novel compositions and kits comprising at least one nitric oxide enhancing diuretic compound, or pharmaceutically acceptable salts thereof, and, optionally, at least one nitric oxide enhancing compound and/or at least one therapeutic agent. The invention also provides methods for (a) treating conditions resulting from excessive water and/or electrolyte retention; (b) treating cardiovascular diseases; (c) treating renovascular diseases; (d) treating diabetes; (e) treating diseases resulting from oxidative stress; (f) treating endothelial dysfunctions; (g) treating diseases caused by endothelial dysfunctions; (h) treating cirrhosis; (j) treating pre-eclampsia; (k) treating osteoporosis; (l) treating nephropathy; (m) treating peripheral vascular diseases; (n) treating portal hypertension; (o) treating central nervous system disorders; (p) treating metabolic syndrome; (q) treating sexual dysfunctions; and (r) hyperlipidemia. The nitric oxide enhancing diuretic compounds comprise at least one nitric oxide enhancing group linked to the diuretic compound through one or more sites such as carbon, oxygen and/or nitrogen via a bond or moiety that cannot be hydrolyzed.

  该发明描述了包含至少一种增强一氧化氮利尿化合物或其药用盐的新型组合物和试剂盒，以及可选地，至少一种增强一氧化氮化合物和/或至少一种治疗剂的试剂盒。该发明还提供了以下方法：(a)治疗由过多水分和/或电解贮留引起的症状；(b)治疗心血管疾病；(c)治疗肾血管疾病；(d)治疗糖尿病；(e)治疗由氧化应激引起的疾病；(f)治疗内皮功能障碍；(g)治疗由内皮功能障碍引起的疾病；(h)治疗肝硬化；(j)治疗子痫前期；(k)治疗骨质疏松症；(l)治疗肾病；(m)治疗外周血管疾病；(n)治疗门静脉高压；(o)治疗中枢神经系统疾病；(p)治疗代谢综合征；(q)治疗性功能障碍；以及(r)高脂血症。增强一氧化氮利尿化合物包括至少一种增强一氧化氮基团，通过碳、氧和/或氮等一个或多个位点与利尿化合物连接，连接通过不能水解的键或基团。
• A comparison of X-ray crystal structures including methyl 3,5-bis(hydroxymethyl)benzoate, its phenylethynyl extended derivative in polymorphous forms and the corresponding carboxylic acids
  作者：Felix Katzsch、Diana Eißmann、Edwin Weber

  DOI：10.1007/s11224-011-9858-0

  日期：2012.2

  Considering the specific supramolecular synthon design of carboxylic acid and alcoholic hydroxyl groups in the field of crystal engineering, we compared the solid state structures of particular benzoates and corresponding acids 1–4 both in the non-spacered (1, 2) and spacered (3, 4) forms. Based on the single crystal X-ray study, there is only a slight influence of the phenylacetylene spacer with regard to the layer lattice arrangement of the benzoates while referring to the benzoic acid analogues the addition of the spacer gives rise to a modification of the lattice from a layer to a tape structure. Dependent on the crystallization conditions, two crystalline polymorphs of compound 3 (3a, 3b) were obtained and discussed regarding their structural differences.

  考虑到晶体工程领域中羧酸和醇羟基特定超分子单体设计，我们比较了特定苯甲酸盐及其对应酸1-4在无间隔（1, 2）和有间隔（3, 4）形式中的固态结构。根据单晶X射线研究，苯甲酸盐的层状晶格排列在加入苯乙炔间隔基时仅有轻微影响，而参照苯甲酸类似物，间隔基的加入导致晶格结构从层状转变为带状。根据结晶条件，化合物3获得了两种晶型多晶型物（3a, 3b），并讨论了它们在结构上的差异。