cis-2-phenethyl-6-isopropyl-3,6-dihydro-2H-pyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: cis-2-phenethyl-6-isopropyl-3,6-dihydro-2H-pyran
• 英文别名: (2S,6R)-2-(2-phenylethyl)-6-propan-2-yl-3,6-dihydro-2H-pyran
• 化学式: C₁₆H₂₂O
• 分子量: 230.35
• InChiKey: FSJYGXFLWHAIFR-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-5-甲基己-3-烯-2-酮 在 双(乙腈)氯化钯(II) 咪唑 、 sodium tetrahydroborate 、 cerium(III) chloride 、 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 cis-2-phenethyl-6-isopropyl-3,6-dihydro-2H-pyran
  参考文献：
  名称：

  Pd II-催化的四氢和3,6-二氢[2 H ]吡喃环的立体定向形成：通过分子内的氧基palpalation反应进行的1,3-手性转移

  摘要：

  描述了2,6-二取代的四氢吡喃和3,6-二氢[2 H ]吡喃的立体有择合成。在温和条件下，Pd II催化的羟基亲核试剂向烯丙基醇的环化反应有效发生，仲烯丙基醇上的立体生成中心通过syn -S N 2'型过程转移至吡喃环上新生成的立体生成中心。。

  DOI：

  10.1016/j.tetasy.2005.02.006

文献信息

• Studies on the Synthesis of 2,6-Disubstituted Dihydropyrans: Intervention of Oxonia-Cope Rearrangements in the Lewis Acid Mediated Cyclodehydrative Reactions of Aldehydes and β-Hydroxyallylsilanes
  作者：William R. Roush、Garrett J. Dilley

  DOI：10.1055/s-2001-14632

  日期：——

  The dehydrative coupling reactions of anti-b-hydroxyallylsilanes 5 and aldehydes provide 2,6-cis-dihydropyrans 27 by pathways involving oxonium ions that cyclize via boat-like transition state 21, with the intervention of oxonia-Cope rearrangements (21 ® 29).

  抗 b-羟基烯丙基硅烷 5 和醛的脱水偶联反应通过涉及氧鎓离子的途径提供 2,6-顺式二氢吡喃 27，氧鎓离子通过船状过渡态 21 环化，并参与 oxonia-Cope 重排 (21 ® 29) .
• Bi(OTf)₃-, TfOH-, and TMSOTf-Mediated, One-Pot Epoxide Rearrangement, Addition, and Intramolecular Silyl-Modified Sakurai (ISMS) Cascade toward Dihydropyrans: Comparison of Catalysts and Role of Bi(OTf)₃
  作者：R. Frederick Lambert、Robert J. Hinkle、Stephen E. Ammann、Yajing Lian、Jia Liu、Shane E. Lewis、Robert D. Pike

  DOI：10.1021/jo201478d

  日期：2011.11.18

  Catalytic quantities of bismuth(III) triflate efficiently initiate the rearrangement of epoxides to aldehydes, which subsequently react with (Z)-delta-hydroxyalkenylsilanes to afford 2,6-disubstituted 3,6-dihydro-2H-pyrans. Isolated yields of desired products using Bi(OTf)(3) were compared with yields obtained when the reactions were run with TfOH and TMSOTf in the presence and absence of several additives. These studies, as well as NMR spectroscopic analyses, indicate an initial Lewis acid/base interaction between Bi(OTf)(3) and substrates providing TfOH in situ.
• PdII-Catalyzed stereospecific formation of tetrahydro- and 3,6-dihydro[2H]pyran rings: 1,3-chirality transfer by intramolecular oxypalladation reaction
  作者：Jun’ichi Uenishi、Masashi Ohmi、Atsushi Ueda

  DOI：10.1016/j.tetasy.2005.02.006

  日期：2005.4

  The stereospecific synthesis of 2,6-disubstituted tetrahydropyran and 3,6-dihydro[2H]pyran is described. The PdII-catalyzed cyclization of the hydroxy nucleophile to the allylic alcohol takes place efficiently under mild conditions, with the stereogenic center on the secondary allylic alcohol transfers to a newly generated stereogenic center on pyran ring via a syn-SN2′ type process.

  描述了2,6-二取代的四氢吡喃和3,6-二氢[2 H ]吡喃的立体有择合成。在温和条件下，Pd II催化的羟基亲核试剂向烯丙基醇的环化反应有效发生，仲烯丙基醇上的立体生成中心通过syn -S N 2'型过程转移至吡喃环上新生成的立体生成中心。。