3-(4-chlorophenoxy)-2-hydroxypropionic acid | 7698-98-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-chlorophenoxy)-2-hydroxypropionic acid
• 英文别名: d,l-3-(p-Chlorphenoxy)milchsaeure；3-(p-chlorophenoxy)-lactic acid；2-hydroxy 3-p-chlorophenoxy propanoic acid；3-(4-Chlorophenoxy)-2-hydroxypropanoic acid
• CAS: 7698-98-8
• 化学式: C₉H₉ClO₄
• 分子量: 216.621
• InChiKey: HYNAIYBUUSJFKL-UHFFFAOYSA-N

物化性质

• 熔点：
  135-136 °C
• 沸点：
  368.0±27.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenoxy)-2-hydroxypropionic acid 、 硫酸二甲酯 在 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到3-(4-Chloro-phenoxy)-2-hydroxy-propionic acid methyl ester
  参考文献：
  名称：

  Enantioselective preparation of 2-alkyl-3-aryloxypropionic acids and esters and 3-alkyl-4-chromanones

  摘要：

  Lipases provided access to chiral 2-alkyl-3-aryloxypropionic acids that gave chiral 3-alkyl-4-chromanones with high enantioselectivity.

  DOI：

  10.1016/0040-4039(92)88162-x
• 作为产物：
  描述：

  Alpha,4-二氯茴香醚 在 氢氧化钾 、 sodium hydride 作用下， 以 乙醇 、 xylene 为溶剂， 反应 122.75h， 生成 3-(4-chlorophenoxy)-2-hydroxypropionic acid
  参考文献：
  名称：

  Enantioselective preparation of 2-alkyl-3-aryloxypropionic acids and esters and 3-alkyl-4-chromanones

  摘要：

  Lipases provided access to chiral 2-alkyl-3-aryloxypropionic acids that gave chiral 3-alkyl-4-chromanones with high enantioselectivity.

  DOI：

  10.1016/0040-4039(92)88162-x
• 作为试剂：
  描述：

  、 chlorolactic acid 、 对氯苯酚 、 盐酸 在 水 、 3-(4-chlorophenoxy)-2-hydroxypropionic acid 作用下， 以 sodium hydroxide 为溶剂， 反应 2.0h， 生成 3-(4-chlorophenoxy)-2-hydroxypropionic acid
  参考文献：
  名称：

  T-Butyl-phenoxy-alkylene esters of benzoic and nicotinic acids,

  摘要：

  提供了具有结构的p-烷基或环烷基苯氧基烷醇和酯：##STR1## 其中：R.sub.1是具有1至6个碳原子的烷基，最好是三级的，更好的是叔丁基；或与苯基在相邻环碳上紧密结合的二价环烷基，例如在茚中；R.sub.2是具有1至3个碳原子的低级烷基或氢；R.sub.3是羟基或酯基，所述酯基选自由未取代和羟基取代的一元羧酸和二元羧酸，所述酸选自包括具有1至约12个碳原子的脂肪族酸，包括碳酸酯，具有3至约12个碳原子的环脂肪族酸，具有6至约20个碳原子的碳氢芳香族酸和具有5至约12个碳原子的氮杂环芳香族酸，其中R.sub.4是一价的脂肪族，环烷基，芳香族或氮杂环芳香族，R.sub.5是二价的脂肪族，环烷基，芳香族或氮杂环芳香族，所述酸被醇酯化，所述醇具有1至6个碳原子；和碳酸单烷酯，所述烷基具有1至3个碳原子；n.sub.1，n.sub.2和n.sub.3分别表示CH.sub.2，C(R.sub.2).sub.2和CH.sub.2基团的数量，并且是在0到10范围内的数字；并且n.sub.1，n.sub.2和n.sub.3中至少有一个不为零。这些化合物通过抑制释放导致过敏疾病症状的化学介质，包括过敏性鼻炎，哮喘，皮肤和胃肠道的过敏反应以及刺激物和引起炎症的物质产生的许多刺激和炎症症状，来抑制特定过敏超敏或特定刺激物引起的异常组织反应。

  公开号：

  US04451474A1

文献信息

• Process for manufacturing phenoxylactic acids, their derivatives and
  申请人：Sucreries du Soissonnais et Compagnie Sucriere

  公开号：US04332959A1

  公开（公告）日：1982-06-01

  The process is for the manufacture of phenoxylactic acids and their derivatives of the general formula: ##STR1## (in which R.sub.1 and R.sub.2, identical or different, can represent hydrogen atoms, methyl residues, methoxy groups or halogens; Y represents an OH or O--CO--R.sub.3 group with R.sub.3 representing either an aliphatic residue possibly substituted by a halogen, or an aromatic residue possibly substituted on the nucleus by one or several methyl, methoxy, halogen groups or lastly a heterocyclic group; Z represents OH group or an ##STR2## with R.sub.4 representing an alkyl or aryl radical and R.sub.5 hydrogen or an alkyl radical, NR.sub.4 R.sub.5 possibly also representing the morpholinyl radical). A cyanhydrin is subjected to a Ritter reaction (reaction with tert. butanol or isobutene in the presence of an acid). The resulting compound is hydrolyzed to obtain the corresponding acid, and if desired, this acid is subjected to conventional reactions for preparing ester-acids, ester-amides or corresponding amides.

  该过程用于制造苯氧乙酸及其衍生物，其一般结构式为：##STR1##（其中R.sub.1和R.sub.2，相同或不同，可以代表氢原子、甲基残基、甲氧基团或卤素；Y代表一个OH或O--CO--R.sub.3基团，其中R.sub.3代表一个可能被卤素取代的脂肪残基，或者一个可能在核上被一个或多个甲基、甲氧基、卤素基取代的芳香残基，最后是一个杂环基团；Z代表一个OH基团或一个##STR2##，其中R.sub.4代表一个烷基或芳基基团，R.sub.5代表氢或一个烷基基团，NR.sub.4 R.sub.5也可能代表吗啡基团）。氰水合物经过里特反应（在酸的存在下与叔丁醇或异丁烯反应）。得到的化合物经水解得到相应的酸，如果需要，这种酸将经过常规反应制备酯酸、酯酰胺或相应酰胺。
• Synthesis and fungicidal activity ofN-2-(3-methoxy-4-propargyloxy) phenethyl amides. Part 3: stretched and heterocyclic mandelamide oomyceticides
  作者：Clemens Lamberth、Hans-Joachim Kempf、Miroslav Križ

  DOI：10.1002/ps.1308

  日期：2007.1

  Novel analogues of mandipropamid have been designed and prepared. The synthetic approach to these stretched and heterocyclic mandelamides is outlined. Biological data demonstrate their high efficacy against important plant diseases like tomato and potato late blight (Phytophthora infestans De Bary) and grape downy mildew (Plasmopara viticola Berliner & de Toni). Structure-activity relationship studies

  已经设计和制备了新的曼地拉米类似物。概述了这些拉伸的和杂环的扁桃酰胺的合成方法。生物数据表明，它们对重要的植物病害（如番茄和马铃薯晚疫病（Phytophthora infestans De Bary）和葡萄霜霉病（Plasmopara viticola Berliner＆de Toni））具有很高的功效。讨论了构效关系研究。
• Phenoxy alkanol esters for treatment of allergic conditions
  申请人：Berger; Frank M.

  公开号：US05242936A1

  公开（公告）日：1993-09-07

  Compounds of the formula: ##STR1## wherein R.sub.1 is at position 4 and either is an alkyl group of 1-6 C or is an --(CH.sub.2).sub.3 -- which is additionally linked to the phenyl at position 3 thereof; R.sub.2 is a lower alkyl of 1-3 C or is hydrogen; n.sub.1, n.sub.2 and n.sub.3 represent the number of CH.sub.2, C(R.sub.2).sub.2 and CH.sub.2 groups, respectively, wherein n.sub.1 is 2, 3, 4, 5, 6, 8, or 11, n.sub.2 is 0 or 1 and n.sub.3 is 0 and R.sub.4 is an alkyl residue of 1-12 C or is selected from phenyl and pyridyl; and their pharmaceutical compositions are useful in inhibiting the release of chemical mediators which cause allergic symptoms. Compounds, compositions, and methods for treatment of allergic conditions are disclosed.

  化学式为：##STR1##的化合物，其中R.sub.1位于位置4，可以是1-6个碳的烷基或是与其位置3的苯基额外连接的--(CH.sub.2).sub.3 -；R.sub.2是1-3个碳的低烷基或氢；n.sub.1，n.sub.2和n.sub.3分别表示CH.sub.2，C(R.sub.2).sub.2和CH.sub.2的数目，其中n.sub.1为2、3、4、5、6、8或11，n.sub.2为0或1，n.sub.3为0，R.sub.4为1-12个碳的烷基残基或选择自苯基和吡啶基；它们的药物组成物在抑制导致过敏症状的化学介质释放方面有用。公开了用于治疗过敏症状的化合物、组成物和方法。
• P-alkyl phenoxy alkanols for the treatment of allergic conditions
  申请人：Berger; Frank M.

  公开号：US05021460A1

  公开（公告）日：1991-06-04

  p-Alkyl or cycloalkyl phenoxy alkanols and esters are provided having the structure: ##STR1## in which: R.sub.1 is an alkyl group having from one to six carbon atoms, preferably tertiary, and still more preferably tertiary-butul; or a bivalent cycloalkylene group condensed with the phenyl group at adjacent ring carbons thereof, such as in indane; R.sub.2 is lower alkyl having from one to three carbon atoms or hydrogen; R.sub.3 is hydroxyl or an ester group selected from the group consisting of COOR.sub.4 and OOCR.sub.4 derived from unsubstituted and hydroxy-substituted monocarboxylic acids and COOR.sub.5 OOC and OOCR.sub.5 COO derived from unsubstituted and hydroxy-substituted dicarboxylic acids, the acids being selected from the group consisting of aliphatic acids, including carbamic acid, having from one to about twelve carbon atoms; cycloaliphatic acids having from three to about twelve carbon atoms; carbocyclic aromatic acids having from six to about twenty carbon atoms; and nitrogen heterocyclic aromatic acids having from five to about twelve carbon atoms, R.sub.4 being monovalent aliphatic, cycloaliphatic, aromatic, or nitrogen heterocyclic aromatic, and R.sub.5 being divalent aliphatic, cycloaliphatic, aromatic, or nitrogen heterocyclic aromatic, the acids being esterified with aliphatic alcohols having from one to six carbon atoms; and carbonic acid monoalkyl esters, the alkyl having from one to three carbon atoms; and n.sub.1, n.sub.2 and n.sub.3 represent the number of CH.sub.2, C(R.sub.2),.sub.2 and CH.sub.2 groups, respectively, and are numbers within the range from 0 to 10; and at least one of n.sub.1, n.sub.2 and n.sub.3 is other than zero. These compounds inhibit abnormal tissue reactivity due to specific allergic hypersensitivity or due to specific irritants by inhibiting the release of chemical mediators that are responsible for the symptoms of allergic diseases, including allergic rhinitis, asthma, hypersensitivity of the skin and of the gastrointestinal canal, and the many symptoms of irritation and inflammation produced by irritants and inflammation-causing substances, and prevent rejection of transplanted cells and organs and particularly of bone marrow and insulin-producing Langerhans cells.

  提供了具有以下结构的p-烷基或环烷基苯氧基烷醇和酯类化合物：##STR1## 其中：R.sub.1是具有1至6个碳原子的烷基，优选是三级的，更优选是三级丁基；或者是与苯基相邻环碳原子上紧密连接的二价环烷基，例如在茚中；R.sub.2是具有1至3个碳原子的低级烷基或氢；R.sub.3是羟基或酯基，所述酯基选自由未取代和羟基取代的一元羧酸和二元羧酸，所述酸选自具有1至约12个碳原子的脂肪族酸，包括碳酸酯酸；具有3至约12个碳原子的环脂肪族酸；具有6至约20个碳原子的碳环芳香族酸；以及具有5至约12个碳原子的氮杂环芳香族酸，其中R.sub.4是一价的脂肪族、环脂肪族、芳香族或氮杂环芳香族，而R.sub.5是二价的脂肪族、环脂肪族、芳香族或氮杂环芳香族，所述酸被烷基醇酯化，所述烷基具有1至6个碳原子；以及碳酸单烷酯，所述烷基具有1至3个碳原子；n.sub.1、n.sub.2和n.sub.3分别代表CH.sub.2、C(R.sub.2),.sub.2和CH.sub.2基团的数量，且它们是在0至10范围内的数字；并且至少一个n.sub.1、n.sub.2和n.sub.3不为零。这些化合物通过抑制释放导致过敏性疾病症状的化学介质，包括过敏性鼻炎、哮喘、皮肤和胃肠道的过敏性，以及刺激物和引起炎症的物质产生的许多刺激和炎症症状，抑制异常组织反应，防止移植细胞和器官的排异反应，特别是骨髓和胰岛素产生的朗格汉斯细胞的排异反应。
• P-Alkyl or cycloalkyl phenoxy alkanols and alkanol esters and process
  申请人：Berger; Frank M.

  公开号：US04543362A1

  公开（公告）日：1985-09-24

  p-Alkyl or cycloalkyl phenoxy alkanols and esters are provided having the structure: ##STR1## in which: R.sub.1 is an alkyl group having from one to six carbon atoms, preferably tertiary, and still more preferably tertiary-butyl; or a bivalent cycloalkylene group condensed with the phenyl group at adjacent ring carbons thereof, such as in indane; R.sub.2 is lower alkyl having from one to three carbon atoms or hydrogen; R.sub.3 is hydroxyl or an ester group selected from the group consisting of COOR.sub.4 and OOCR.sub.4 derived from unsubstituted and hydroxy-substituted monocarboxylic acids and COOR.sub.5 OOC and OOCR.sub.5 COO derived from unsubstituted and hydroxy-substituted dicarboxylic acids, the acids being selected from the group consisting of aliphatic acids, including carbamic acid, having from one to about twelve carbon atoms; cycloaliphatic acids having from three to about twelve carbon atoms; carbocyclic aromatic acids having from six to about twenty carbon atoms; and nitrogen heterocyclic aromatic acids having from five to about twelve carbon atoms, R.sub.4 being monovalent aliphatic, cycloaliphatic, aromatic, or nitrogen heterocyclic aromatic, and R.sub.5 being divalent aliphatic, cycloaliphatic, aromatic, or nitrogen heterocyclic aromatic, the acids being esterified with aliphatic alcohols having from one to six carbon atoms; and carbonic acid monoalkyl esters, the alkyl having from one to three carbon atoms; and n.sub.1, n.sub.2 and n.sub.3 represent the number of CH.sub.2, C(R.sub.2).sub.2 and CH.sub.2 groups, respectively, and are numbers within the range from 0 to 10; and at least one of n.sub.1, n.sub.2 and n.sub.3 is other than zero. These compounds inhibit abnormal tissue reactivity due to specific allergic hypersensitivity or due to specific irritants by inhibiting the release of chemical mediators.

  提供p-烷基或环烷基苯氧基脂肪醇和酯，其结构为：##STR1## 其中：R.sub.1是具有1至6个碳原子的烷基，优选是三级的，更优选是叔丁基；或是与苯基相邻环碳原子上凝结的二价环烷基，例如在茚中；R.sub.2是具有1至3个碳原子的低级烷基或氢；R.sub.3是羟基或酯基，所述酯基选自由未取代和羟基取代的单羧酸和由未取代和羟基取代的二羧酸衍生的COOR.sub.4和OOCR.sub.5 COO，所述酸选自包括具有1至约12个碳原子的脂肪酸，包括碳酸酯，具有从3到约12个碳原子的环脂肪酸，具有从6到约20个碳原子的碳环芳香酸和具有从5到约12个碳原子的氮杂环芳香酸，其中R.sub.4是一价的脂肪烷基，环脂肪烷基，芳香族或氮杂环芳香族，R.sub.5是二价的脂肪烷基，环脂肪烷基，芳香族或氮杂环芳香族，所述酸被醇类醇酯化，其碳原子数为1至6；和碳酸单烷基酯，该烷基具有从1至3个碳原子；n.sub.1，n.sub.2和n.sub.3分别代表CH.sub.2，C(R.sub.2).sub.2和CH.sub.2基团的数量，分别是从0到10的数字；并且n.sub.1，n.sub.2和n.sub.3中至少有一个不为零。这些化合物通过抑制化学介质的释放来抑制由特定过敏过敏或特定刺激物引起的异常组织反应。