2-(3,4-dihydro-2(H)-pyran-6-yl)-2-propanol | 72081-22-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3,4-dihydro-2(H)-pyran-6-yl)-2-propanol
• 英文别名: 2-(3,4-dihydro-2H-pyran-6-yl)-2-propanol；2-(3,4-dihydro-2H-pyran-6-yl)propan-2-ol
• CAS: 72081-22-2
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: GPFMJJMEPGMZTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2-(3,4-dihydro-2(H)-pyran-6-yl)-2-propanol 在 溴 、 二甲基亚砜 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 13.0h， 生成 5-methyl-8,9-dihydro-7H-furo[3,4-f]chromene-1,3-dione
  参考文献：
  名称：

  Lebouc, Alain; Delaunay, Jacques; Riobe, Olivier, Journal of Chemical Research, Miniprint, 1980, # 6, p. 2683 - 2690

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 丙酮 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 18.0h， 生成 2-(3,4-dihydro-2(H)-pyran-6-yl)-2-propanol
  参考文献：
  名称：

  用于不对称金催化的单点结合配体：具有 TADDOL 相关但无环骨架的亚磷酰胺

  摘要：

  将 TADDOL 相关二醇与无环骨架结合的现成亚磷酰胺被证明是不对称金催化的极好配体，允许以良好到出色的对映选择性进行许多机械不同的转化。这包括烯-丙二烯的 [2 + 2] 和 [4 + 2] 环加成、烯炔的环异构化、形成二氢吲哚的加氢芳基化反应，以及丙二烯的分子内加氢胺化和加氢烷氧基化。有效合成抗抑郁药物候选 (-)-GSK 1360707 的应用强调了它们的制备相关性。新配体的独特设计元素是它们的无环二甲醚骨架代替了传统的（异亚丙基）缩醛部分特征塔多尔的。

  DOI：

  10.1021/ja303641p

文献信息

• Cyclic vinyl ether carbanions—II
  作者：Robert K. Boeckman、Kenneth J. Bruza

  DOI：10.1016/s0040-4020(01)93274-0

  日期：——

  Conditions for metalation of a variety of cyclic vinyl ethers and reaction of the resulting carbanions with electrophiles are described. Effects of the vinyl ether structure on the relative rates of metalation are discussed. Applications of this methodology to the construction of various types of carbonyl compounds are presented.

  描述了各种环状乙烯基醚的金属化条件以及所得碳负离子与亲电子试剂的反应条件。讨论了乙烯基醚结构对相对金属化速率的影响。介绍了该方法在各种类型羰基化合物的构建中的应用。
• Synthesis and reactions of .alpha.-methylene-.beta.-keto sulfones
  作者：Andreas Weichert、H. Martin R. Hoffmann

  DOI：10.1021/jo00013a007

  日期：1991.6

  Modified Jones oxidation of 2-(benzenesulfonyl)-2-alken-1-ols and rapid nonnucleophilic workup below 0-degrees-C yields a variety of alpha-methylene-beta-keto sulfones 4, including crystalline parent 4a and also e-h, which can be stored at -20-degrees-C without change. In the absence of nucleophiles, the new compounds are stable (heating in benzene) toward dimerization and polymerization. Thus, selective cross-reactions are feasible. With alcohols, including sterically hindered tertiary alcohols and also with 2-(ethoxycarbonyl)cyclopentanone, the compounds function as efficient Micheal acceptors, even in the absence of base catalysis. In moist ether, 2-(benzenesulfonyl)-1-penten-3-one (4b) suffers rearrangement to 2-(benzenesulfonyl)ethyl propanoate (9). Sulfonylated alcohol 7 and strained alpha-hydroxyoxetane 8 are assumed as intermediates. Toward electron-rich aromatics and heteroaromatics, alpha-methylene-beta-keto sulfones 4 behave as electrophiles in Friedel-Crafts-type functionalizations. The new compounds are also dienophilic: of the two groups (acetyl and benzenesulfonyl) attached to the ethylenic terminus in 4a, benzenesulfonyl has been found to preferentially adopt the endo position in cycloadditions of cyclopentadiene and also cyclohexadiene. Prototype 3-(benzenesulfonyl)-3-buten-2-one (4a) is a crystalline methyl vinyl ketone (MVK) equivalent which, unlike MVK, undergoes controlled free-radical additions with nucleophilic radicals. In hetero-Diels-Alder reactions, 4a serves as a 1-oxa-1,3-butadiene unit, combining with a wide range of alkenes of graded nucleophilicity. Electron deficient 4a also reacts as an enophile toward 1,1-dialkylated ethylenes. In the presence of ZnCl2.OEt2, the ene reaction with beta-piene can be suppressed completely in favor of cycloaddition, giving a robustadial building block in 85% yield. In further applications to natural products chemistry, the synthesis of frontalin and novel oxatricyclics are described.
• A Facile Access to Densely Functionalized Substituted Cyclopentanes and Spiro Cyclopentanes. Carbocation Stabilization Directed Bond Migration in Rearrangement of Cyclobutanes
  作者：Azizul Haque、Anjan Ghatak、Subrata Ghosh、Nanda Ghoshal

  DOI：10.1021/jo970283m

  日期：1997.7.1
• LEBOUC A.; DELYUNAY J.; RIOBE O., SYNTHESIS, 1979, NO 8, 610-613
  作者：LEBOUC A.、 DELYUNAY J.、 RIOBE O.

  DOI：——

  日期：——
• LEBOUC A.; DELAUNAY J.; RIOBE O., J. CHEM. RES. SYNOP., 1980, NO 6, 187
  作者：LEBOUC A.、 DELAUNAY J.、 RIOBE O.

  DOI：——

  日期：——