1,5-di(acetoxy)hexane | 140238-28-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,5-di(acetoxy)hexane
• 英文别名: 1,5-Hexanediol diacetate；5-acetyloxyhexyl acetate
• CAS: 140238-28-4
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: LFUBGEAPBLTTCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-di(acetoxy)hexane 生成 间戊二烯 、 1,3-己二烯 、 1,4-己二烯 、 2,4-己二烯
  参考文献：
  名称：

  Paul; Tchelitcheff, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1946, vol. 223, p. 1137,1138

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基四氢吡喃 、 乙酸酐 在 硫酸 作用下， 反应 20.0h， 以39%的产率得到1,5-di(acetoxy)hexane
  参考文献：
  名称：

  硫酸-乙酸酐使环状醚开环

  摘要：

  环醚（例如四氢呋喃或四氢吡喃）很容易在室温下被硫酸-乙酸酐裂解，以高收率提供相应的二乙酰氧基烷烃。不论取代基的存在如何，开环均适用于饱和环醚。

  DOI：

  10.1002/jhet.5570370555

文献信息

• Mild and practical acylation of alcohols with esters or acetic anhydride under distannoxane catalysis
  作者：Akihiro Orita、Katsumasa Sakamoto、Yuji Hamada、Akihiro Mitsutome、Junzo Otera

  DOI：10.1016/s0040-4020(99)00072-1

  日期：1999.3

  Distannoxane catalysts effect acylation of alcohols by action of esters and acetic anhydride. In particular, use of enol esters provides an extremely useful method. Primary alcohols are acylated in preference to secondary ones as well as phenol. Both acid- and base-sensitive functional groups remain intact. Especially unique is the discrimination of thio function which is completely tolerant under

  二锡氧烷催化剂通过酯和乙酸酐的作用实现醇的酰化。特别地，使用烯醇酯提供了非常有用的方法。伯醇优先于仲醇和苯酚被酰化。对酸和碱敏感的官能团均保持完整。尤其独特的是在当前反应条件下完全耐受的硫官能团的鉴别。由于操作非常简单，因此该方法非常实用。无需纯化即可使用酯类和溶剂，并且不需要惰性气氛。可以简单地通过柱色谱法或蒸馏来分离产物，而无需进行水后处理。
• Selective acylation of a sterically hindered hydroxyl group of unsymmetrical diols containing a primary hydroxyl group such as 1,5-hexanediol in the presence of silica gel with acetyl chloride
  作者：Haruo Ogawa、Yuko Ide、Ryoichi Honda、Teiji Chihara

  DOI：10.1002/poc.622

  日期：2003.6

  selectively formed in the presence of silica gel with acetyl chloride by refluxing a suspension of unsymmetrical diols containing a primary hydroxyl group such as 1,5-hexanediol preadsorbed on silica gel. Such regioselectivity was observed through preferential adsorption via a primary hydroxyl group of the diols. Copyright © 2003 John Wiley & Sons, Ltd.

  在硅胶与乙酰氯的存在下，通过回流预吸附在硅胶上的含伯羟基的不对称二醇（如1,5-己二醇）的悬浮液，选择性地形成受阻更大的单乙酸酯。通过经由二醇的伯羟基的优先吸附观察到这种区域选择性。版权所有©2003 John Wiley＆Sons，Ltd.
• Highly Selective Acylation of Alcohols Using Enol Esters Catalyzed by Iminophosphoranes
  作者：Palanichamy Ilankumaran、John G. Verkade

  DOI：10.1021/jo990928d

  日期：1999.12.1

  The iminophosphorane bases PhCH2N=P(MeNCH2CR2)(3)N and PhCH2N=P(NMe2)(3) catalyze the acylation of primary alcohols with enol esters in excellent yields and in high selectivity. It was found that acid labile groups such as acetal and epoxide survive under the reaction conditions. Groups such as TBS and disulfide, which undergo cleavage in the presence of Ac2O and the Lewis acid Sc(OTf)(3), are also unaffected. Diene, conjugated acetylene, oxazoline, nitro, and benzodioxane groups are also compatible with our catalyst/reagent system. Because secondary alcohols do not react under our conditions, our methodology is attractive for the selective acylation of primary alcohols. Polymer-supported iminophosphorane catalysts are also shown to be useful in these reactions, thus opening the possibility of wider applications.
• Distannoxane-Catalyzed Highly Selective Acylation of Alcohols
  作者：Akihiro Orita、Akihiro Mitsutome、Junzo Otera

  DOI：10.1021/jo9800412

  日期：1998.4.1
• Paul, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1939, vol. 208, p. 588
  作者：Paul

  DOI：——

  日期：——