3-羟基-4-(1,1-二甲基乙基)-2,6-二甲基苯乙腈 | 55699-10-0

• 物质功能分类: 有机原料 - 腈类化合物
• 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: 3-羟基-4-(1,1-二甲基乙基)-2,6-二甲基苯乙腈
• 中文别名: 4-叔丁基-3-羟基-2,6-二甲苯基乙腈
• 英文名称: 2-(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)acetonitrile
• 英文别名: 4-t-butyl-2,6-dimethyl-3-hydroxy-1-phenylacetonitrile；2,6-dimethyl-3-hydroxy-4-t-butylphenylacetonitrile；4-tert-butyl-3-hydroxy-2,6-xylylacetonitrile；4-tert.-Butyl-2,6-dimethyl-3-hydroxyphenylacetonitrile；4-tert-Butyl-2,6-dimethyl-3-hydroxyphenylacetonitrile
• CAS: 55699-10-0
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: OUKJZHRCKQJXSU-UHFFFAOYSA-N

物化性质

• 熔点：
  125 °C(Solv: ethanol (64-17-5))
• 沸点：
  341.3±37.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（少量溶解）、乙酸乙酯（轻微溶解、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

制备方法与用途

化学性质：结晶状，熔点为122-130℃。

用途：作为氧甲唑啉的中间体。

生产方法：

1. 以叔丁醇与间二甲苯缩合生成3,5-二甲基叔丁苯。
2. 再用甲醛、氯化氢进行氯甲基化，得到4-叔丁基-2,6-二甲基氯苄。
3. 然后使用乙酸酐和冰醋酸酯化，获得4-叔丁基-2,6-二甲基苄基乙酸酯。
4. 进行硝化、水解并氯化，得到4-叔丁基-2,6-二甲基-3-硝基氯苄。
5. 最终通过氰化、还原（针对硝基）、重氮化和水解等步骤制得目标产品。

反应信息

• 作为反应物：
  描述：

  3-羟基-4-(1,1-二甲基乙基)-2,6-二甲基苯乙腈 在 三氯化铝 作用下， 以 苯 为溶剂， 以84%的产率得到2-(3-Hydroxy-2,6-dimethylphenyl)acetonitrile
  参考文献：
  名称：

  Raju, B.; Rao, G. S. Krishna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 469 - 470

  摘要：

  DOI：
• 作为产物：
  描述：

  2-叔丁基-3-氯甲基-4,6-二甲基苯酚 、 氰化钾 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以92%的产率得到3-羟基-4-(1,1-二甲基乙基)-2,6-二甲基苯乙腈
  参考文献：
  名称：

  Raju, B.; Rao, G. S. Krishna, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 469 - 470

  摘要：

  DOI：

文献信息

• Synthesis of [2H4]oxymetazoline and [14C]oxymetazoline
  作者：Michelle L. Brugger、Scott Borges、Sumei Ren、Paul McNamara

  DOI：10.1002/jlcr.1805

  日期：2010.12

  An efficient synthesis of [2H4] and [14C]oxymetazoline has been developed. Both compounds follow the same synthetic route with the introduction of the label occurring at different synthetic steps. The synthesis of [2H4]oxymetazoline from [2H4]ethylene diamine was achieved in one step with a 40% yield. The synthesis of [14C]oxymetazoline from potassium [14C]cyanide was achieved in two steps with an overall radiochemical yield of 67%. Copyright © 2010 John Wiley & Sons, Ltd.

  已开发出高效合成[2H4]和[14C]氧美氟特的工艺。这两种化合物遵循相同的合成路径，只是在不同的合成步骤中引入了标记。从[2H4]乙二胺合成[2H4]氧美氟特可在一步内完成，产率为40%。而从钾[14C]氰化物合成[14C]氧美氟特则需要两步，总放射化学产率为67%。版权所有 © 2010 John Wiley & Sons, Ltd.
• 2,4,6-Trialkyl L-3-hydroxyphenylalkanoates
  申请人：Ciba-Geigy Corporation

  公开号：US03988363A1

  公开（公告）日：1976-10-26

  Ester and amides having the formula ##SPC1## Wherein R, R.sup.1 and R.sup.2 are independently lower alkyl or cycloalkyl groups, R.sup.3 is hydrogen, alkyl, cycloalkyl, alkylene, phenyl, phenyl substituted by alkyl groups, alkylthioethyl, thiobis-alkylene, alkyleneoxyalkylene, polyoxyalkylene or a polyvalent cyclic or acyclic hydrocarbon radical, R.sup.4 is hydrogen, lower alkyl, cycloalkyl, R.sup.5 is hydrogen, alkyl, phenyl, phenyl substituted by alkyl groups, alkylene, a polyvalent cyclic or acyclic hydrocarbon radical or alkyleneoxyalkylene, A is lower alkylene, m is 1 to 4 and n is 1 to 6. The esters are prepared by usual esterification procedures from a suitable alcohol and an acid of the formula III ##SPC2## or an acid halide or acid anhydride thereof. The higher alkyl esters can also be prepared from the lower alkyl ester, especially the methyl ester, by transesterification with a higher alkanol or polyol. The amides are prepared by usual amidation procedures by reacting a carboxylic acid of formula III, an acid chloride, anhydride or a lower alkyl ester thereof with the appropriate amine. The nitriles corresponding to acids of formula III are prepared as well as some malonate esters derived having the formula V. ##SPC3## The compounds are useful as stabilizers or organic materials, especially polyolefins, which deteriorate upon exposure to light and heat.

  酯和酰胺的化学式为##SPC1##其中R、R.sup.1和R.sup.2分别是独立的低烷基或环烷基基团，R.sup.3是氢、烷基、环烷基、烷基烯、苯基、烷基硫乙基、硫代双烷基、烷基氧基烷基、聚氧基烷基或多价环烷基或非环烷基烃基，R.sup.4是氢、低烷基、环烷基，R.sup.5是氢、烷基、苯基、烷基苯基、烷基烯、多价环烷基或非环烷基烃基或烷基氧基烷基，A是低烷基烯，m为1到4，n为1到6。酯通过常规酯化程序从适当的醇和化学式III的酸或其酸卤或酸酐制备而成。高烷基酯也可通过与较高烷醇或聚醇的酯交换反应，特别是与低烷基酯，尤其是甲酯进行制备。酰胺通过常规酰胺化程序，通过将化学式III的羧酸、酸氯、酸酐或其低烷基酯与适当的胺反应制备而成。相应于化学式III的酸的腈也被制备，以及一些具有化学式V的马隆酸酯衍生物。这些化合物可用作稳定剂或有机材料，特别是在光照和热力作用下会退化的聚烯烃的稳定剂。
• [EN] A TOPICAL COMPOSITION FOR TREATING ROSACEA AND A METHOD FOR TREATING ROSACEA WITH THE SAME<br/>[FR] COMPOSITION TOPIQUE DE TRAITEMENT DE LA ROSACÉE ET PROCÉDÉ DE TRAITEMENT DE LA ROSACÉE AVEC CELLE-CI
  申请人：WHITCUP SCOTT

  公开号：WO2018218116A1

  公开（公告）日：2018-11-29

  A composition for use in the treatment of rosacea includes a multi-kinase inhibitor that inhibits both a Vascular Endothelial Growth Factor Receptor and a Fibroblast Growth Factor Receptor. A method for treating rosacea for a patient includes inhibiting a Vascular Endothelial Growth Factor Receptor of the patient; and inhibiting a Fibroblast Growth Factor Receptor of the patient.

  用于治疗酒渣鼻的复合物包括一种多激酶抑制剂，该抑制剂既抑制血管内皮生长因子受体，又抑制成纤维细胞生长因子受体。一种治疗患有酒渣鼻的患者的方法包括抑制患者的血管内皮生长因子受体；和抑制患者的成纤维细胞生长因子受体。
• Amides of 2,4,6-trialkyl-3-hydroxyphenylalkanoic acids
  申请人：Ciba-Geigy Corporation

  公开号：US04187246A1

  公开（公告）日：1980-02-05

  Ester and amides having the formula ##STR1## wherein R, R.sup.1 and R.sup.2 are independently lower alkyl or cycloalkyl groups, R.sup.3 is hydrogen, alkyl, cycloalkyl, alkylene, phenyl, phenyl substituted by alkyl groups, alkylthioethyl, thiobis-alkylene, alkyleneoxyalkylene, polyoxyalkylene or a polyvalent cyclic or acyclic hydrocarbon radical, R.sup.4 is hydrogen, lower alkyl, cycloalkyl, R.sup.5 is hydrogen, alkyl, phenyl, phenyl substituted by alkyl groups, alkylene, a polyvalent cyclic or acyclic hydrocarbon radical or alkyleneoxyalkylene, A is lower alkylene, m is 1 to 4 and n is 1 to 6. The compounds are useful as stabilizers of organic materials, especially polyolefins, which deteriorate upon exposure to light and heat.

  具有以下式子的酰胺和酯类化合物：##STR1## 其中R，R.sup.1和R.sup.2分别独立为低碳基或环烷基，R.sup.3为氢、烷基、环烷基、烷基烷基、苯基、被烷基取代的苯基、烷基硫乙基、硫代双烷基、烷基氧烷基、聚氧烷基或多价环烷基或非环烷基碳氢基，R.sup.4为氢、低碳基、环烷基，R.sup.5为氢、烷基、苯基、被烷基取代的苯基、烷基烷基、多价环烷基或非环烷基碳氢基或烷基氧烷基，A为低碳基烷基，m为1到4，n为1到6。该化合物可用作有机材料的稳定剂，特别是聚烯烃，在光和热的作用下会恶化。
• 2,4,6-Trialkyl-3-hydroxybenzylmalonate
  申请人：Ciba-Geigy Corporation

  公开号：US04196301A1

  公开（公告）日：1980-04-01

  Ester and amides having the formula ##STR1## wherein R, R.sup.1 and R.sup.2 are independently lower alkyl or cycloalkyl groups, R.sup.3 is hydrogen, alkyl, cycloalkyl, alkylene, phenyl, phenyl substituted by alkyl groups, alkylthioethyl, thiobis-alkylene, alkyleneoxyalkylene, polyoxyalkylene or a polyvalent cyclic or acyclic hydrocarbon radical, R.sup.4 is hydrogen, lower alkyl, cycloalkyl, R.sup.5 is hydrogen, alkyl, phenyl, phenyl substituted by alkyl groups, alkylene, a polyvalent cyclic or acyclic hydrocarbon radical or alkyleneoxyalkylene, A is lower alkylene, m is 1 to 4 and n is 1 to 6.

  具有以下式子的酯和酰胺：##STR1## 其中，R、R.sup.1和R.sup.2分别是独立的较低烷基或环烷基，R.sup.3是氢、烷基、环烷基、烷基烷基、苯基、被烷基取代的苯基、烷基硫乙基、硫代双亚烷基、烷基氧烷基、聚氧烷基或多价环烷基或非环烷基碳氢基团，R.sup.4是氢、较低烷基、环烷基，R.sup.5是氢、烷基、苯基、被烷基取代的苯基、烷基烷基、多价环烷基或非环烷基碳氢基团或烷基氧烷基，A是较低烷基烷基，m为1到4，n为1到6。