4-羟基-3-羟基甲基苯甲醛 | 54030-32-9

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-羟基-3-羟基甲基苯甲醛
• 英文名称: 4-hydroxy-3-(hydroxymethyl)benzaldehyde
• 英文别名: vanillin
• CAS: 54030-32-9
• 化学式: C₈H₈O₃
• mdl: MFCD00114698
• 分子量: 152.15
• InChiKey: SCXZNYRQOPBUTM-UHFFFAOYSA-N

物化性质

• 熔点：
  142-145 °C
• 沸点：
  342.6±32.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2912499000
• 储存条件：
  2-8°C，惰性气体

反应信息

• 作为反应物：
  描述：

  4-羟基-3-羟基甲基苯甲醛 在 吡啶 、 叔丁基过氧化氢 、 N,N-二异丙基乙胺 、 三氯化磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 7.5h， 生成 2-[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinine-6-carbaldehyde
  参考文献：
  名称：

  Enzymatically Activated cycloSal-d4T-monophosphates:  The Third Generation of cycloSal-Pronucleotides

  摘要：

  The third generation of cycloSal-pronucleotides, 5-diacetoxymethyl-cycloSal-d4T-monophosphates (5-di-AM-cycloSal-d4TMPs), is reported as a new class of "lock-in"-modified cycloSal-pronucleotides. These compounds bear an esterase-cleavable geminal dicarboxylate (acylal) attached to the aromatic ring of the saligenyl unit. The conversion into a strong acceptor group (aldehyde) leads to a strong decrease in hydrolytic stability. As a consequence, a fast release of a nucleoside monophosphate (i.e., d4TMP) follows. The concept of this enzymatic activation is proven by hydrolysis studies in phosphate buffer, cell extracts, and human serum. These investigations showed the conversion of the acylal group into a polar aldehyde by enzymatic cleavage. Besides, antiviral activities against HIV are presented.

  DOI：

  10.1021/jm0613267
• 作为产物：
  描述：

  2,2-二甲基-4H-苯并[d][1,3]二噁英-6-甲醛 在 盐酸 作用下， 以 乙腈 为溶剂， 以81%的产率得到4-羟基-3-羟基甲基苯甲醛
  参考文献：
  名称：

  5-Diacetoxymethyl-cycloSal-d4TMP—A prototype of enzymatically activatedcycloSal-pronucleotides

  摘要：

  A new class of "lock-in" modified cyclo Sal-pronucleotides has been synthesized. On the example of 5-diacetoxymethyl-cycloSal-d4T-monophosphate (5-di-AM-cycloSal-d4TMP), the concept of enzymatically activated cycloSal-pronucleotides is elucidated. Synthesis, hydrolysis studies, and antiviral activities against HIV are presented.

  DOI：

  10.1080/15257770701504025

文献信息

• Tricyclic pyrazole derivatives
  申请人：BASF Aktiengesellschaft

  公开号：US06462036B1

  公开（公告）日：2002-10-08

  This invention relates to certain 3-aryl or 3-heteroaryl pyrazoles with 4,5(3,4)-bicyclic ring fusion which are inhibitors of protein kinase activity, of which some are novel compounds, to pharmaceutical compositions containing these pyrazoles and to processes for preparing these pyrazoles.

  这项发明涉及具有4,5(3,4)-双环融合的3-芳基或3-杂芳基吡唑，这些化合物是蛋白激酶活性抑制剂，其中一些是新颖化合物，涉及含有这些吡唑的药物组合物以及制备这些吡唑的方法。
• One-Pot Synthesis of N-Substituted β-Amino Alcohols from Aldehydes and Isocyanides
  作者：Răzvan C. Cioc、Daan J. H. van der Niet、Elwin Janssen、Eelco Ruijter、Romano V. A. Orru

  DOI：10.1002/chem.201500210

  日期：2015.5.18

  A practical two‐stage one‐pot synthesis of N‐substituted β‐amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon–carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon

  已经开发出一种实用的两步法一锅法合成N-取代的β-氨基醇，该方法以醛和异氰酸酯为起始原料。该方法的特点是反应条件温和，范围广，对官能团的耐受性强。该协议基于较少见的中心碳-碳键断开连接，对涉及胺和各种碳亲电试剂（环氧化物，α-卤代酮，β-卤代醇）的传统方法进行了补充。如有关抗哮喘药沙丁胺醇的合成所示，可以从简单的结构单元中以简洁有效的方式制备药用相关产品。将合成物升级为对映选择性变体也是可行的。
• Lignin Oxidation and Products Thereof
  申请人：Albizati Kim

  公开号：US20120107886A1

  公开（公告）日：2012-05-03

  Provided herein is a method of oxidizing lignin. Further disclosed herein are aromatic and non-aromatic compounds obtained from oxidized lignin.

  本文提供了一种氧化木质素的方法。此外，还披露了从氧化木质素中获得的芳香和非芳香化合物。
• Benzylidene thiazolidinediones and their use as antimycotic agents
  申请人：Oxford GlycoSciences (UK) Ltd

  公开号：US20040006112A1

  公开（公告）日：2004-01-08

  A compound of formula I or a salt thereof wherein, A is O or S, X and Y independently represent O, CH 2 and may be the same or different, Q is (CH 2 ) m —CH(R1)—(CH 2 ) n , R is OR6, NHR8, R1 is hydrogen, or optionally substituted alkyl, R2 and R3 are independently hydrogen, or specific substituents, provided that R2 and R3 are not both H, and R4 and R5 are hydrogen or specific substituents, m is 0-3; n is 0-2; are useful in the treatment of fungal infections.

  公式I的化合物或其盐，其中，A为O或S，X和Y分别代表O、CH2，可以相同也可以不同，Q为(CH2)m—CH(R1)—(CH2)n，R为OR6，NHR8，R1为氢，或者可选择地取代的烷基，R2和R3独立地为氢，或者特定的取代基，但要求R2和R3不同时为H，R4和R5为氢或者特定的取代基，m为0-3；n为0-2；在治疗真菌感染中是有用的。
• Optically active nitro alcohol derivatives, optically active amino alcohol derivatives, and process for producing thereof
  申请人：——

  公开号：US20020193447A1

  公开（公告）日：2002-12-19

  Optically active 1-substituted phenyl-2-nitro alcohol derivatives having the formula (1) 1 and the process for producing thereof, and 1-substituted phenyl-2-amino alcohol derivatives having the formula (2) 2 and the process for producing thereof from the optically active 1-substituted phenyl-2-nitro alcohol derivatives. From these nitro alcohols, pharmaceuticals such as (R)-albutamin and (R)-sarmeterol useful as a bronchodilator is obtained via optically active amino alcohols which are useful pharmaceutical intermediates.

  具有下列化学式（1）的具有光学活性的1-取代苯基-2-硝基醇衍生物及其生产方法，以及具有下列化学式（2）的具有光学活性的1-取代苯基-2-氨基醇衍生物及其生产方法，从这些具有光学活性的1-取代苯基-2-硝基醇衍生物中生产。通过这些硝基醇，可以制得用作支气管扩张剂的药物，如（R）-阿布特拉明和（R）-沙米特罗尔，其通过有用的药用中间体光学活性氨基醇制得。