5,5-dimethyl-1,3-hexanediol | 138490-32-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5,5-dimethyl-1,3-hexanediol
• 英文别名: 5,5-dimethylhexane-1,3-diol
• CAS: 138490-32-1
• 化学式: C₈H₁₈O₂
• 分子量: 146.23
• InChiKey: ZFACQEJYDWSKSG-UHFFFAOYSA-N

物化性质

• 沸点：
  231.0±8.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  4
• 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

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-1,3-hexanediol 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (4S,6R,8R,11S)-4-(2,2-dimethylpropyl)-8-methyl-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019
• 作为产物：
  描述：

  3,3-二甲基丁醛 在 lithium aluminium tetrahydride 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 5,5-dimethyl-1,3-hexanediol
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019

文献信息

• Enantioselective acetalization of racemic 1,3-alkanediols with l-methone under kinetically controlled conditions
  作者：Toshiro Harada、Sachi Tanaka、Akira Oku

  DOI：10.1016/s0040-4020(01)89438-2

  日期：——

  (derived from 1) in preference to spiroacetal 4 (derived from ent-1). The kinetically controlled acetalization is applied to a novel kinetic resolution of racemic 1,3-alkanediols: Optically active diols ent-1 of 55–95 % ee are obtained when the racemic diols are allowed to react with 1.5 equiv of enol silyl ether 10 under similar conditions.

  外消旋的1,3-链烷二醇（rac -1）通过在三氟甲磺酸（10 mol％）存在下用1-甲基烯醇三甲基甲硅烷基醚（10）处理进行对映选择性缩醛化反应，从而得到热力学上较不稳定的螺缩醛3（由1衍生）。优先于螺乙缩醛4（源自ent -1）。动力学控制缩醛化被施加到外消旋的1,3-链烷二醇的新颖动力学拆分：光学活性二醇ENT -1 55-95％ee值时的外消旋二醇使其与烯醇甲硅烷基醚1.5当量反应得到10 在相似的条件下。
• [EN] PROCESS FOR OBTAINING (S)-2-BENZYL-4-((3AR,7AS)-HEXAHYDRO-1 H-ISOINDOL- 2(3H)-YL)-4-OXOBUTANOIC ACID AND SALTS THEREOF<br/>[FR] PROCÉDÉ POUR L'OBTENTION D'ACIDE (S)-2-BENZYL-4-((3AR,7AS)-HEXAHYDRO-1H-ISOINDOL-2(3H)-YL)-4-OXOBUTANOÏQUE ET DE SELS DE CELUI-CI
  申请人：LESVI LABORATORIOS SL

  公开号：WO2013189829A1

  公开（公告）日：2013-12-27

  Comprising reacting compound (IV) with compound (V) in a solvent to give (S)-mitiglinide (II) and compound (III) as a by- product; removing the solvent and adding ethyl acetate to precipitate compound (III); collecting the solid and applying at least one cycle process comprising: - refluxing the solution of compound (III) with an organic solvent to give (S)-mitiglinide (II) and further compound (III) as a by-product, - removing the organic solvent and adding ethyl acetate to precipitate compound (III); and - separating the mother liquors from the solid, and mixing all the mother liquors; removing the ethyl acetate from the mother liquors to obtain (S)-mitiglinide.

  将化合物（IV）与化合物（V）在溶剂中反应，得到（S）-米格林肽（II）和化合物（III）作为副产物；去除溶剂并加入乙酸乙酯以沉淀化合物（III）；收集固体并应用至少一个循环过程，包括：- 用有机溶剂回流化合物（III）的溶液，得到（S）-米格林肽（II）和进一步的化合物（III）作为副产物，- 去除有机溶剂并加入乙酸乙酯以沉淀化合物（III）；- 将母液与固体分离，并混合所有母液；从母液中去除乙酸乙酯以获得（S）-米格林肽。
• PREPARATION OF DIHYDROPYRIDINES
  申请人：VISHNU NEWADKAR RAVINDRANATH

  公开号：US20110275825A1

  公开（公告）日：2011-11-10

  The invention relates to a method and compounds for the preparation of clevidipine butyrate, a very short acting hypertensive calcium antagonist, as well as the synthesis of these compounds useful for the preparation of clevidipine (also known as clevidipine butyrate). Moreover the invention also discloses polymorphic forms of clevidipine butyrate, useful for the preparation of pharmaceutical compositions, and processes to prepare them.

  该发明涉及一种用于制备克莱维地平丁酸酯的方法和化合物，克莱维地平丁酸酯是一种作用时间非常短的高血压钙拮抗剂，以及用于制备克莱维地平（也称为克莱维地平丁酸酯）的这些化合物的合成。此外，该发明还揭示了克莱维地平丁酸酯的多态形式，用于制备药物组合物，并揭示了用于制备这些多态形式的方法。
• [EN] PROCESS FOR PREPARING PRASUGREL<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE PRASUGREL
  申请人：LESVI LABORATORIOS SL

  公开号：WO2013014295A1

  公开（公告）日：2013-01-31

  The present invention is directed to an improved process for preparing, prasugrel and maleate salt of Prasugrel and, optionally other pharmaceutically acceptable salts from, prasugrel and said maleate salt, in high yields and purity, which can be used at industrial scale. The process of the present invention comprises the steps of bromination, condensation, acetylating and optionally converting into maleate salt and, if desired, conversion into another pharmaceutically acceptable salt from it. The present process is advantageous in terms of productivity, efficacy, purity and also prevents the use of toxic substances.

  本发明涉及一种改进的制备过程，用于从prasugrel和prasugrel的maleate盐，以及可选地从prasugrel和该maleate盐中制备其他药用盐，高产率和纯度中制备，可用于工业规模。本发明的过程包括溴化、缩合、乙酰化以及可选地转化为maleate盐，并如有需要，从中转化为另一种药用盐。本过程在生产效率、功效、纯度方面具有优势，并且还能防止使用有毒物质。
• Nail varnish composition comprising at least one polymer and at least one plasticizer
  申请人：Ilekti Philippe

  公开号：US20050220731A1

  公开（公告）日：2005-10-06

  The present disclosure relates to a nail varnish composition comprising, in a cosmetically acceptable medium comprising an organic solvent medium, at least one block polymer and at least one plasticizer, such that when the composition forms a film, the film exhibits a water uptake of less than or equal to 10%. The present disclosure also relates to a process comprising applying such a composition to the nails to give a film which can be glossy, can have good holding power, and can be water-resistant on nails.

  本公开涉及一种指甲油组合物，包括至少一种块状聚合物和至少一种增塑剂，其中所述组合物在包含有机溶剂介质的美容可接受介质中，当所述组合物形成膜时，所述膜的吸水率小于或等于10％。本公开还涉及一种工艺，包括将这种组合物涂抹在指甲上，形成可以有光泽，具有良好持久力和防水性的膜。