6-(tetrahydro-2H-pyran-2-yloxy)hexyl acetate | 120540-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 6-(tetrahydro-2H-pyran-2-yloxy)hexyl acetate
• 英文别名: 6-(Oxan-2-yloxy)hexyl acetate；6-(oxan-2-yloxy)hexyl acetate
• CAS: 120540-21-8
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: LPTCIGZNQXNGAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(tetrahydro-2H-pyran-2-yloxy)hexyl acetate 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-(5-Hydroxypentan-1-yl)-1,3-dithiane
  参考文献：
  名称：

  Differentiation between carbonyls and acetals in 1,3-dithiane and 1,3-dithiolane synthesis catalyzed by organotin triflates

  摘要：

  Carbonyls and acetals are converted to 1,3-dithianes and -dithiolanes upon treatment with 2-stanna-1,3-dithianes and -dithiolanes under catalysis by organotin triflates. In these competition reactions, various types of carbonyls and acetals are differentiated. Aldehydes react preferentially over ketones, but the preference is completely reversed in the competition reactions between the corresponding acetals and ketals. The reactivity of aliphatic aldehydes is greater than that of the acetals of aliphatic aldehydes and ketones. Conversely, an aromatic acetal is more reactive than its parent aldehyde. In the competition between aromatic and aliphatic aldehydes, the reaction of the latter predominates. However, aromatic acetals react preferentially over aliphatic acetals. Ketones of different types are also differentiated. No such discrimination can be achieved by conventional methods. Organotin triflates are capable of detecting subtle differences in the reactivity of carbonyls and acetals. Such unique differentiation can be explained in terms of the dependence of the reaction path on the substrate: the reactions of carbonyls are initiated by coordination to tin, whereas the reactions of acetals proceed via oxocarbenium ion intermediates.

  DOI：

  10.1021/jo00070a038
• 作为产物：
  描述：

  6-(tetrahydro-2H-pyranyloxy)hexan-1-ol 、 乙酸酐 在 lanthanum(III) nitrate 作用下， 反应 0.25h， 以98%的产率得到6-(tetrahydro-2H-pyran-2-yloxy)hexyl acetate
  参考文献：
  名称：

  在无溶剂条件下，使用La（NO 3）3 ·6H 2 O作为催化剂，用乙酸酐对醇，酚和胺进行温和高效的乙酰化反应

  摘要：

  在室温下，在无溶剂条件下，在催化量的La（NO 3）3 ·6H 2 O的存在下，通过用乙酸酐处理，可以将各种醇，酚和胺有效，选择性地转化为相应的乙酸酯。该方法与酸敏感的羟基保护基团（例如TBDMS，THP，OBz，OBn，Boc和一些异丙叉）兼容，并提供1,3-，1,4-和1,5-二醇单乙酸酯的优异收率。

  DOI：

  10.1016/j.tetlet.2006.07.059

文献信息

• A mild and efficient acetylation of alcohols, phenols and amines with acetic anhydride using La(NO3)3·6H2O as a catalyst under solvent-free conditions
  作者：T. Srikanth Reddy、M. Narasimhulu、N. Suryakiran、K. Chinni Mahesh、K. Ashalatha、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2006.07.059

  日期：2006.9

  A wide variety of alcohols, phenols and amines are efficiently and selectively converted into the corresponding acetates by treatment with acetic anhydride in the presence of catalytic amounts of La(NO3)3·6H2O under solvent-free conditions at room temperature. The method is compatible with acid sensitive hydroxyl protecting groups such as TBDMS, THP, OBz, OBn, Boc and some isopropylidenes and offers

  在室温下，在无溶剂条件下，在催化量的La（NO 3）3 ·6H 2 O的存在下，通过用乙酸酐处理，可以将各种醇，酚和胺有效，选择性地转化为相应的乙酸酯。该方法与酸敏感的羟基保护基团（例如TBDMS，THP，OBz，OBn，Boc和一些异丙叉）兼容，并提供1,3-，1,4-和1,5-二醇单乙酸酯的优异收率。
• <i>N,N</i>-Diarylammonium Pyrosulfate as a Highly Effective Reverse Micelle-Type Catalyst for Hydrolysis of Esters
  作者：Yoshiki Koshikari、Akira Sakakura、Kazuaki Ishihara

  DOI：10.1021/ol301290c

  日期：2012.6.15

  Reverse micelle-type N,N-diarylammonium pyrosulfate (3–5 mol %) efficiently catalyzes the hydrolysis of esters (up to 100 mmol scale) under organic solvent-free conditions. The present method is successfully applied to the hydrolysis of various esters without the decomposition of the base-sensitive moieties and without any loss of optical purity for α-heterosubstituted carboxylic acids.

  反胶束型N，N-焦硫酸二芳基铵（3-5摩尔％）在无有机溶剂的条件下有效催化酯的水解（最大100 mmol规模）。本方法成功地用于各种酯的水解，而没有碱敏感部分的分解，并且对于α-杂取代的羧酸没有任何光学纯度的损失。
• Solid State Acetylation with Acetylimidazole: Selective Protection of Primary Alcohols and Phenols
  作者：Hisahiro Hagiwara、Kimie Morohashi、Toshio Suzuki、Masayoshi Ando、Isao Yamamoto、Michiharu Kato

  DOI：10.1080/00397919808007174

  日期：1998.6

  Abstract Primary alcohols and phenols have been acetylated with acetylimidazole by the solid state reaction, grinding both substrates with a pestle in a mortar.

  摘要 伯醇和酚通过固态反应与乙酰咪唑乙酰化，在研钵中用研杵研磨两种基材。
• Activation and synthetic applications of thiostannanes. Deprotection and transformations of tetrahydropyranyl ethers
  作者：Tsuneo Sato、Junzo Otera、Hitosi Nozaki

  DOI：10.1021/jo00302a057

  日期：1990.7
• Tris(pentafluorophenyl)borane catalyzed acylation of alcohols, phenols, amines, and thiophenols under solvent-free condition
  作者：Santosh Kumar Prajapti、Atulya Nagarsenkar、Bathini Nagendra Babu

  DOI：10.1016/j.tetlet.2014.01.124

  日期：2014.3

  The acylation of alcohols, phenols, amines, and thiophenols was accomplished with 0.5 mol % of tris (Pentafluorophenyl)borane [B(C6E5)(3)] at ambient temperature under solvent-free condition. Major advantages of this method include high yield, short reaction time, simple procedure, compatibility with sensitive protecting groups as well as other functional groups, absence of racemization of optical active compounds, and epimerization of sugars. 2014 Elsevier Ltd. All rights reserved.