1,1-dimethoxy-butan-2-ol | 7472-25-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-dimethoxy-butan-2-ol
• 英文别名: 2-hydroxy-butyraldehyde dimethyl acetal；2-Hydroxy-butyraldehyd-dimethylacetal；1,1-Dimethoxybutan-2-ol
• CAS: 7472-25-5
• 化学式: C₆H₁₄O₃
• 分子量: 134.175
• InChiKey: MINVDNAALYQBTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-dimethoxy-butan-2-ol 在 Dowex AG-50W-X₈ (H(+) form) 水 作用下， 反应 36.0h， 生成 (+/-)-2-hydroxybutanal
  参考文献：
  名称：

  Substrate specificity and carbohydrate synthesis using transketolase

  摘要：

  This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis. The properties of transketolase from both yeast and spinach were investigated. The yeast enzyme was found to be more convenient for routine use. Examination of the substrate specificity of yeast transketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates. A practical protocol for transketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.

  DOI：

  10.1021/jo00048a023
• 作为产物：
  描述：

  2-Chlorobutanal 、 sodium methylate 在 甲醇 作用下， 生成 1,1-dimethoxy-butan-2-ol
  参考文献：
  名称：

  Kirrmann et al., Bulletin de la Societe Chimique de France, 1958, p. 1469,1474

  摘要：

  DOI：

文献信息

• 4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions
  作者：Michael J Burns、Thomas O Ronson、Richard J K Taylor、Ian J S Fairlamb

  DOI：10.3762/bjoc.10.116

  日期：——

  Two mild and efficient strategies have been developed for the O-functionalisation of 4-hydroxy-6-alkyl-2-pyrones, by using them as nucleophilic partners in oxa-Michael additions and the Mitsunobu reaction. The reactions proceed in moderate to excellent yields on a range of substrates containing useful functionality. The reactions serve as practical and valuable synthetic methods to construct complex 2-pyronyl ethers, which are found embedded in a number of natural products.

  已开发了两种温和高效的策略，用于将4-羟基-6-烷基-2-吡喃烯氧化功能化，通过将它们用作氧杂Michael加成和三冈反应中的亲核试剂。这些反应在包含有用官能团的一系列底物上以中等至优良的产率进行。这些反应作为实用且有价值的合成方法，用于构建复杂的2-吡喃醚，这些醚嵌入在许多天然产物中。
• Structure and conformation of heterocycles. 13. conformational analysis of 2,3-DI(R)OXY-1,4-dioxanes: anomeric and gauche effects
  作者：Benzion Fuchs、Aviyakar Ellencweig、Ulrich Burkert†

  DOI：10.1016/s0040-4020(01)88441-6

  日期：1984.1

  A series of trans- and cis-2,3-di R)oxy-1,4-dIoxanes (R = Me,Ph, Ac) and some 2,5-disubstituted analogis were prepared and analysed by various NMR techniques. The trans isomers occur in more than 96% as diaxial conformers. Molecular mechanics calculations largely confirm these findings, which are interpreted -in terms of combined anomeric and gauche effects.

  制备了一系列反式和顺式-2,3-二R）氧基-1,4-二恶烷（R = Me，Ph，Ac）和一些2,5-二取代的类似物，并通过各种NMR技术进行了分析。反式异构体以双轴构象异构体的形式存在于96％以上。分子力学计算在很大程度上证实了这些发现，这些发现是根据端基异构和网状效应的组合来解释的。
• Chemical and enzymatic syntheses of 6-deoxyhexoses. Conversion to 2,5-dimethyl-4-hydroxy-2,3-dihydrofuran-3-one (Furaneol) and analogs
  作者：Chi Huey Wong、Francois P. Mazenod、George M. Whitesides

  DOI：10.1021/jo00168a023

  日期：1983.10
• Epoxyethers. VII. Reaction of α-Haloaldehydes with Base
  作者：Calvin L. Stevens、Eugene Farkas、Bernard Gillis

  DOI：10.1021/ja01639a029

  日期：1954.5
• Kirrmann,A.; Joschek,H.-I., Bulletin de la Societe Chimique de France, 1963, p. 1681 - 1684
  作者：Kirrmann,A.、Joschek,H.-I.

  DOI：——

  日期：——