cis-2-benzyltetrahydro-2H-pyran-4-ol

• 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: cis-2-benzyltetrahydro-2H-pyran-4-ol
• 英文别名: (2S,4S)-2-benzyloxan-4-ol
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: BMKHAXBXHPGZPN-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 、 3-丁烯-1-醇 在 cellulose-SO₃H 作用下， 以 硝基甲烷 为溶剂， 反应 0.92h， 以86%的产率得到cis-2-benzyltetrahydro-2H-pyran-4-ol
  参考文献：
  名称：

  Cellulose-SO3H as a recyclable catalyst for the synthesis of tetrahydropyranols via Prins cyclization

  摘要：

  Tetrahydropyranols are prepared in good yields and with high cis-selectivity by means of the Prins cyclization using cellulose-sulfonic acid under mild reaction conditions. This is the first report on the preparation of tetrahydropyranols using epoxides and homoallylic alcohols via Prins cyclization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.015

文献信息

• Bismuth triflate catalyzed prins-type cyclization in ionic liquid: Synthesis of 4-tetrahydropyranol derivatives
  作者：M. S. R. Murty、K. Rajasekhar、V. Harikrishna、J. S. Yadav

  DOI：10.1002/hc.20403

  日期：2008.1

  The reaction of aldehydes with homoallylic alcohols in the presence of catalytic amount of bismuth triflate in [bmim]PF6generates 4-tetrahydropyranol derivatives in excellent yield and with high diastereoselectivity. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:104–106, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20403

  在催化量的 [bmim] PF6 中的三氟甲磺酸铋存在下，醛与高烯丙醇的反应以优异的收率和高非对映选择性生成 4-四氢吡喃醇衍生物。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:104–106, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20403
• The ‘Aqueous’ Prins Cyclization: A Diastereoselective Synthesis of 4-Hydroxytetrahydropyran Derivatives
  作者：Jhillu Yadav、Basi Subba Reddy、Gunda Narayana Kumar、Seema Aravind

  DOI：10.1055/s-2007-1000932

  日期：2008.2

  Phosphomolybdic acid (H3PMo12O40, a heteropoly acid) is found to catalyze efficiently the Prins cyclization of homoallylic alcohols with aldehydes in water at room temperature to provide tetrahydropyran-4-ol derivatives in high yields with all cis-selectivity. Only cyclic ketones can give spirocyclic products. The use of phosphomolybdic acid in water makes this procedure simple, more convenient, cost-effective, and environmentally friendly.

  研究发现，磷钼酸（H3PMo12O40，一种杂多酸）可在室温下高效催化同源烯丙基醇与醛在水中的普林斯环化反应，以高产率和全顺选择性提供四氢吡喃-4-醇衍生物。只有环酮才能生成螺环产物。在水中使用磷钼酸使这一过程变得简单、方便、经济和环保。
• Cellulose-SO3H as a recyclable catalyst for the synthesis of tetrahydropyranols via Prins cyclization
  作者：B.V. Subba Reddy、A. Venkateswarlu、G.G.K.S. Narayana Kumar、A. Vinu

  DOI：10.1016/j.tetlet.2010.10.015

  日期：2010.12

  Tetrahydropyranols are prepared in good yields and with high cis-selectivity by means of the Prins cyclization using cellulose-sulfonic acid under mild reaction conditions. This is the first report on the preparation of tetrahydropyranols using epoxides and homoallylic alcohols via Prins cyclization. (C) 2010 Elsevier Ltd. All rights reserved.