2,2,4-trimethyl-pentane-1,3-diol | 144-19-4

• 物质功能分类: 催化剂及助剂 - 塑料橡胶助剂 - 增塑剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,4-trimethyl-pentane-1,3-diol
• 英文别名: 2,2,4-Trimethyl-pentandiol-(1,3)；(3R)-2,2,4-trimethylpentane-1,3-diol
• CAS: 144-19-4；127894-68-2
• 化学式: C₈H₁₈O₂
• 分子量: 146.23
• InChiKey: JCTXKRPTIMZBJT-SSDOTTSWSA-N

物化性质

• 熔点：
  50-53 °C (lit.)
• 沸点：
  232 °C (lit.)
• 密度：
  0,937 g/cm3
• 闪点：
  >230 °F
• 溶解度：
  可溶于氯仿、甲醇
• LogP：
  1.25 at 22℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  1
• RTECS号：
  SA1400000
• 海关编码：
  2905399090
• 包装等级：
  Z01
• 安全说明：
  S26,S37/39
• 危险标志：
  GHS07
• 危险性描述：
  H302,H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338

制备方法与用途

概述

2,2,4-三甲基-1,3-戊二醇（简称TMPD）是Texanol醇酯和TXIB增塑剂的重要有机化工中间体，常用于合成不饱和聚酯、印刷油墨、表面活性剂、增塑剂、合成润滑油、驱虫剂、香料、聚氨酯以及萃取剂等产品。因此，它在表面涂料和石油加工等行业中显示出广泛用途和很高的商业价值。

制备

将带有滴液漏斗、冷凝系统和温度计的三口烧瓶预热至一定温度，并加入一定浓度的NaOH水溶液，在N₂保护下进行磁力搅拌。缓慢滴加50g异丁醛，反应结束后自然降至室温，进行水洗和静置分液。回收碱液，取上层液体做气相色谱分析，结果表明异丁醛转化率为99%，产物选择性为99.5%，单程收率同样达到99.5%。分离出的油层通过减压蒸馏得到2,2,4-三甲基-1,3-戊二醇；经GC分析后，其质量分数达到99.08%。

化学性质

2,2,4-三甲基-1,3-戊二醇为白色结晶体。该化合物易溶于醇、酮和芳烃类溶剂，但难溶于水及脂肪烃中。

用途

这种化合物主要用于制造聚酯树脂与涂料用醇酸树脂，还用于合成酯类产品，在涂料、塑料中作为增塑剂等。此外，它还被应用于GB18582001 内墙装饰用乳胶漆检测中的VOC气相检测，并可用于液体涂料的饱和聚酯树脂、水性聚酯树脂、不饱和聚酯树脂、醇酸树脂、聚氨基甲酸乙酯、增塑剂中间体、印刷油墨、合成香料、表面活性剂和驱虫剂等产品的制备。

反应信息

• 作为反应物：
  描述：

  2,2,4-trimethyl-pentane-1,3-diol 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (R)-3-hydroxy-2,2,4-trimethylpentyl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Isoleucine-Catalyzed Direct Asymmetric Aldol Addition of Enolizable Aldehydes

  摘要：

  Isoleucine-catalyzed direct enantioselective aldol additions between enolizable aldehydes are reported. Intermediate acetal structures dictate the configurative outcome and were supported by a hydrogen bond. This direct isoleucine-catalyzed aldol addition represents a welcome complement to both proline- and histidine-catalyzed aldol additions of enolizable aldehydes.

  DOI：

  10.1021/ol300754n
• 作为产物：
  描述：

  (R)-3-hydroxy-2,2,4-trimethylpentanal 在 sodium tetrahydroborate 作用下， 以 异丙醇 为溶剂， 生成 2,2,4-trimethyl-pentane-1,3-diol
  参考文献：
  名称：

  Isoleucine-Catalyzed Direct Asymmetric Aldol Addition of Enolizable Aldehydes

  摘要：

  Isoleucine-catalyzed direct enantioselective aldol additions between enolizable aldehydes are reported. Intermediate acetal structures dictate the configurative outcome and were supported by a hydrogen bond. This direct isoleucine-catalyzed aldol addition represents a welcome complement to both proline- and histidine-catalyzed aldol additions of enolizable aldehydes.

  DOI：

  10.1021/ol300754n

文献信息

• Targeted drugs associated with trimethylamine and/or trimeihylamine-n-oxide
  申请人：Psomagen, Inc.

  公开号：US11424006B2

  公开（公告）日：2022-08-23

  Embodiments of a method and/or system can include administering, to a patient with one or more conditions associated with at least one of TMA, TMAO, and/or derivatives thereof, a therapeutically effective amount of a compound for affecting inhibiting one or more CutC enzymes and/or CntA enzymes associated with microorganisms from at least one taxon from a set of microorganism taxa.

  方法和/或系统的实施方案可包括向患有与 TMA、TMAO 和/或其衍生物中的至少一种相关的一种或多种疾病的患者施用治疗有效量的化合物，以影响抑制与一组微生物类群中至少一个类群的微生物相关的一种或多种 CutC 酶和/或 CntA 酶。
• Asymmetric Acid-Catalyzed Meerwein−Ponndorf−Verley−Aldol Reactions of Enolizable Aldehydes
  作者：Andrea Seifert、Ulf Scheffler、Morris Markert、Rainer Mahrwald

  DOI：10.1021/ol100093u

  日期：2010.4.16

  A highly, stereo- and regioselective Meerwein - Ponndorf - Verley - Aldol etherification process of enolizable aldehydes is described. This new transformation is catalyzed by trifluoroacetic acid. The method also allows cross-aldol reactions with alpha-branched enolizable aldehydes and thus provides access to defined configured quaternary stereogenic centers.
• TARGETED DRUGS ASSOCIATED WITH TRIMETHYLAMINE AND/OR TRIMETHYLAMINE-N-OXIDE
  申请人：Psomagen, Inc.

  公开号：EP3668494A1

  公开（公告）日：2020-06-24
• RIESKE-TYPE OXYGENASE/REDUCTASE TARGETED DRUGS FOR DIAGNOSTIC AND TREATMENT OF DISEASES
  申请人：uBiome, Inc.

  公开号：US20190050525A1

  公开（公告）日：2019-02-14

  Embodiments of a method and/or system can include administering, to a patient with one or more conditions associated with at least one of TMA, TMAO, and/or derivatives thereof, a therapeutically effective amount of a compound for affecting inhibiting one or more CutC enzymes and/or CntA enzymes associated with microorganisms from at least one taxon from a set of microorganism taxa.
• [EN] TARGETED DRUGS ASSOCIATED WITH TRIMETHYLAMINE AND/OR TRIMETHYLAMINE-N-OXIDE<br/>[FR] MÉDICAMENTS CIBLÉS ASSOCIÉS À LA TRIMÉTHYLAMINE ET/OU À LA TRIMÉTHYLAMINE-N-OXYDE
  申请人：UBIOME INC

  公开号：WO2019036507A1

  公开（公告）日：2019-02-21

  Embodiments of a method and/or system can include administering, to a patient with one or more conditions associated with at least one of TMA, TMAO, and/or derivatives thereof, a therapeutically effective amount of a compound for affecting inhibiting one or more CutC enzymes and/or CntA enzymes associated with microorganisms from at least one taxon from a set of microorganism taxa.