(2S,3S,4aR,8aS)-3-(benzyloxy)-2-methyl-2-vinyloctahydropyrano[3,2-b]pyran | 1456889-10-3

• 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: (2S,3S,4aR,8aS)-3-(benzyloxy)-2-methyl-2-vinyloctahydropyrano[3,2-b]pyran
• 英文别名: (2S,3S,4aR,8aS)-2-ethenyl-2-methyl-3-phenylmethoxy-4,4a,6,7,8,8a-hexahydro-3H-pyrano[3,2-b]pyran
• CAS: 1456889-10-3
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: LONJEOWWMCKSRH-MHORFTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 、 四丁基碘化铵 、 双(三甲基硅烷基)氨基钾 、 mercuric triflate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 21.5h， 生成 (2R,3S,4aR,8aS)-3-(benzyloxy)-2-methyl-2-vinyloctahydropyrano[3,2-b]pyran 、 (2S,3S,4aR,8aS)-3-(benzyloxy)-2-methyl-2-vinyloctahydropyrano[3,2-b]pyran
  参考文献：
  名称：

  Synthesis of fused tetrahydropyrans by hydroalkoxylation of δ-hydroxy allenes

  摘要：

  Fused tetrahydropyrans were synthesized by silver(l)- and mercury(II)-mediated intramolecular hydroalkoxylations of delta-hydroxy allenes installed on a tetrahydropyran template. Cyclization of simple allenes was promoted by silver perchlorate to afford vinyl-substituted trans-fused bis-tetrahydropyrans, whereas cyclization of methyl-substituted allenes at the internal allenic carbon atom was achieved more effectively with a catalytic amount of mercuric triflate rather than with silver salts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.026

文献信息

• Stereoselective synthesis of the KJ ring system of yessotoxin by Pd(II)-catalyzed cyclization
  作者：Hajime Yokoyama、Kazuki Nishida、Takashi Togawa、Masaki Yamagami、Masahiro Miyazawa、Yoshiro Hirai

  DOI：10.1016/j.tetlet.2016.08.049

  日期：2016.9

  Yessotoxin was isolated from the digestive glands of the scallop, Patinopecten yessoensis, and would be of use as a promising therapeutic tool. We attained the stereoselective construction of KJ ring system of yessotoxin by the intramolecular cyclization of the trisubstituted allylic alcohol using Pd(II) catalyst.

  Yessotoxin是从扇贝的消化腺（Patinopecten yessoensis）中分离出来的，可用作有前途的治疗工具。我们通过使用Pd（II）催化剂对三取代烯丙基醇进行分子内环化，获得了异毒素KJ环系统的立体选择性结构。