(2R*,4S*)-4-chloro-2-(2-methoxyphenyl)tetrahydro-2H-pyran | 138622-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R*,4S*)-4-chloro-2-(2-methoxyphenyl)tetrahydro-2H-pyran
• 英文别名: cis-2-o-anisyl-4-chloro-tetrahydropyran；(2R,4S)-4-chloro-2-(2-methoxyphenyl)oxane
• CAS: 138622-39-6；138665-69-7
• 化学式: C₁₂H₁₅ClO₂
• 分子量: 226.703
• InChiKey: JZZOFDKMZITBKC-JOYOIKCWSA-N

物化性质

• 沸点：
  335.0±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-丁烯-1-醇 、 2-甲氧基苯甲醛缩二甲醇 生成 (2R*,4S*)-4-chloro-2-(2-methoxyphenyl)tetrahydro-2H-pyran
  参考文献：
  名称：

  Asymmetric synthesis of 2-aryl-tetrahydropyrans via arene chromium tricarbonyl methodology 1: cis-2-Aryl-4-chloro-tetrahydropyrans

  摘要：

  Treatment of acetals derived from ortho substituted benzaldehyde chromium tricarbonyl complexes and methanol with homoallylic alcohol and titanium tetrachloride produces the corresponding (RS,RS,SR,RS)-cis-2-aryl-4-chloro-tetrahydropyran complexes completely diastereoselectively. Thus, by this method, homochiral (R)-(-)-omicron-anisaldehyde chromium tricarbonyl is converted, after decomplexation, to homochiral (R,S)-(+)-cis-2-omicron-anisyl-4-chlorotetrahydropyran.

  DOI：

  10.1016/s0957-4166(00)82002-9

文献信息

• An Efficient Prins Cyclization for Stereoselective Synthesis of Tetrahydropyran from Imines and Homoallyl Alcohols
  作者：Congrong Liu、Daojuan Cheng、Fulai Yang

  DOI：10.1002/cjoc.201400450

  日期：2014.11

  An unprecedented protocol has been developed for the efficient synthesis of substituted tetrahydropyrans via a bismuth‐promoted Prins cyclization of imines with homoallyl alcohols. In the presence of 40 mol% BiCl3, a wide variety of imines react smoothly with homoallyl alcohols at room temperature to give the corresponding 4‐chlorotetrahydropyran derivatives in good to excellent yields.

  已经开发出了一种空前的方案，用于通过铋促进的Prins与高烯丙醇对亚胺的Prins环化反应来高效合成取代的四氢吡喃。在40 mol％BiCl 3的存在下，各种各样的亚胺在室温下与均烯丙基醇平稳反应，以良好的收率得到相应的4-氯四氢吡喃衍生物。
• Unprecedented synergistic effects between weak Lewis and Brønsted acids in Prins cyclization
  作者：Prashant Borkar、Pierre van de Weghe、B. V. Subba Reddy、J. S. Yadav、René Grée

  DOI：10.1039/c2cc35052a

  日期：——

  Novel synergistic effects between Lewis and Brønsted acids in Prins cyclization are reported. Non-reactive Lewis acids and non-reactive Brønsted acids, which failed to perform Prins cyclization when used alone, have shown remarkable synergistic effects when used in combination to perform the reaction successfully.

  报告了路易斯酸和布伦司特酸在普林斯环化反应中的新协同效应。单独使用时不能进行普林斯环化反应的非反应性路易斯酸和非反应性布伦斯特酸，在混合使用时却显示出了显著的协同效应，从而成功地进行了反应。