cis-2-(4-nitrophenyl)-4-hydroxy-tetrahydropyran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-2-(4-nitrophenyl)-4-hydroxy-tetrahydropyran
• 英文别名: (2R,4S)-2-(4-nitrophenyl)oxan-4-ol
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: ZGWLGYHEXFZNKY-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-丁烯-1-醇 、 对硝基苯甲醛 在 bismuth(lll) trifluoromethanesulfonate 水 、 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 反应 0.25h， 以62%的产率得到cis-2-(4-nitrophenyl)-4-hydroxy-tetrahydropyran
  参考文献：
  名称：

  三氟甲磺酸铋催化离子液体中的prins型环化反应：合成4-四氢吡喃醇衍生物

  摘要：

  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

  DOI：

  10.1002/hc.20403

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。
• Diastereoselective Synthesis of 2,4-Disubstituted Tetrahydropyranols and Ethers via a Prins-Type Cyclization Catalyzed by Scandium Triflate
  作者：Wen-Chun Zhang、Chao-Jun Li

  DOI：10.1016/s0040-4020(00)00152-6

  日期：2000.4

  The reaction of aldehydes with homoallylic alcohols catalyzed by scandium triflate gives rise to the formation of 2-substituted tetrahydropyran-4-ols and ethers in good overall yields and with ‘all-cis’ configurations and high diastereoselectivities. The stereochemistries of these products were assigned with the assistance of coupling constants and NOE. Factors affecting the reaction have been examined

  醛与三氟甲磺酸scan催化的均丙醇反应生成了2-取代的四氢吡喃-4-醇和醚，总收率高，具有“顺式”构型和高非对映选择性。这些产物的立体化学在偶合常数和NOE的帮助下进行分配。已经详细研究了影响反应的因素。发现该反应在氯仿中最有效。各种芳香族和脂肪族醛均顺利进行环化。已经提出了用于该反应的催化循环。
• 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.