cis-2-ethyltetrahydropyran-4-ol | 82110-14-3

• 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-ethyltetrahydropyran-4-ol
• 英文别名: cis-2-ethyltetrahydro-2H-pyran-4-ol；2H-Pyran-4-ol, 2-ethyltetrahydro-, (2S-cis)-；(2S,4S)-2-ethyloxan-4-ol
• CAS: 82110-14-3
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: MXUDKCAUJBPFFS-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-2-ethyltetrahydropyran-4-ol 在 正丁基锂 、 二(三叔丁基膦)钯 、 偶氮二甲酸二异丙酯 、 叔丁基锂 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基乙酰胺 、 正戊烷 为溶剂， 反应 20.0h， 生成 ethyl N-[6-cyano-2-(1-methylpyrazole-4-carbonyl)-5-(1-methylpyrazol-4-yl)furo[3,2-b]pyridin-3-yl]-N-[(2S,4S)-2-ethyloxan-4-yl]carbamate
  参考文献：
  名称：

  Multi-gram synthesis of a nucleotide-competing reverse transcriptase inhibitor

  摘要：

  An efficient multi-gram synthesis of a nucleotide-competing reverse transcriptase inhibitor is reported. The synthesis features a chiral auxiliary-assisted alcohol resolution, a Mitsunobu reaction involving a carbamate, followed by a lithium-iodide exchange/Weinreb ketone synthesis tandem. These chemical transformations were optimized in order to increase the yield of the synthesis. The route is concluded by a late-stage palladium-catalyzed cyanation followed by a pyrimidine-2-one ring formation. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2013.01.129
• 作为产物：
  描述：

  Trifluoro-acetic acid (2S,4S)-2-ethyl-tetrahydro-pyran-4-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 cis-2-ethyltetrahydropyran-4-ol
  参考文献：
  名称：

  探讨Prins环化的机理并将其应用于4-羟基四氢吡喃的合成。

  摘要：

  用碳基亲核试剂在Prins环化途径上捕集中间体，可以进一步深入了解影响酸介导的均丙醇与醛反应的因素，从而可以设计出有效合成4-羟基-2,6-二取代四氢吡喃的化合物。

  DOI：

  10.1039/b504562b

文献信息

• [EN] CONDENSED TRICLYCLIC COMPOUNDS AS INHIBITORS OF HIV REPLICATION<br/>[FR] COMPOSÉS TRICYCLIQUES CONDENSÉS EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIH
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2013091096A1

  公开（公告）日：2013-06-27

  Compounds of formula (I) and pharmaceutical compositions thereof: wherein A1 A2 and A3 are each independently selected from the group consisting of N and CR3, wherein R1 is an optionally substituted heterocyclyl or an optionally substituted -(C1-6)alkyl-heterocyclyl, R2 is an optionally substituted aryl or an optionally subsisted heteroaryl, R4 is an optionally substituted aryl, an optionally substituted heterocyclyl or an optionally substituted heteroaryl, useful as an inbitor of HIV replication.

  公式（I）的化合物及其制药组合物：其中A1、A2和A3分别独立地选自N和CR3组成的群，其中R1是可选择地取代的杂环烷基或可选择地取代的-(C1-6)烷基-杂环烷基，R2是可选择地取代的芳基或可选择地取代的杂芳基，R4是可选择地取代的芳基、可选择地取代的杂环烷基或可选择地取代的杂芳基，用作HIV复制抑制剂。
• 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。
• INHIBITORS OF HIV REPLICATION
  申请人：Sturino Claudio

  公开号：US20150011531A1

  公开（公告）日：2015-01-08

  Compounds of formula (I) and pharmaceutical compositions thereof: wherein A 1 A 2 and A 3 are each independently selected from the group consisting of N and CR 3 , wherein R 1 is an optionally substituted heterocyclyl or an optionally substituted —(C 1-6 )alkyl-heterocyclyl, R 2 is an optionally substituted aryl or an optionally subsisted heteroaryl, R 4 is an optionally substituted aryl, an optionally substituted heterocyclyl or an optionally substituted heteroaryl, useful as an inhibitor of HIV replication.

  公式（I）的化合物及其制药组合物：其中A1、A2和A3各自独立地选择自N和CR3组成的群，其中R1是可选取代的杂环基或可选取代的-(C1-6)烷基-杂环基，R2是可选取代的芳基或可选取代的杂芳基，R4是可选取代的芳基、可选取代的杂环基或可选取代的杂芳基，用作HIV复制的抑制剂。
• 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.
• Enzymes in organic synthesis. 25. Heterocyclic ketones as substrates of horse liver alcohol dehydrogenase. Highly stereoselective reductions of 2-substituted tetrahydropyran-4-ones
  作者：J. Anthony Haslegrave、J. Bryan Jones

  DOI：10.1021/ja00381a025

  日期：1982.8