(2R,6R)-2-(furan-2-yl)-4-hydroxy-6-phenyl-5,6-dihydro-2H-pyran-3-carboxylic acid methyl ester | 1314243-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,6R)-2-(furan-2-yl)-4-hydroxy-6-phenyl-5,6-dihydro-2H-pyran-3-carboxylic acid methyl ester
• CAS: 1314243-88-3
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: LGNVDXLCVHZUMF-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  68.9
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  糠醛 、 苯甲醛 、 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 在 titanium(IV) isopropylate 、 (R)-1,1'-Bi-2-naphthol 、 lithium chloride 、 4-甲基苯磺酸吡啶 、 四氯化钛 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 15.6h， 生成 (2R,6R)-2-(furan-2-yl)-4-hydroxy-6-phenyl-5,6-dihydro-2H-pyran-3-carboxylic acid methyl ester 、 (2RS,3SR,6SR)-2-furyl-6-phenyl-4-oxo-tetrahydro-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  An asymmetric Maitland–Japp reaction: a highly enantioselective synthesis of tetrahydropyran-4-ones

  摘要：

  A highly enantioselective synthesis of functionalized tetrahydropyran-4-ones has been achieved by the development of a catalytic asymmetric Maitland-Japp reaction using Chan's diene as the nucleophile. This reaction has been used to synthesize the tetrahydropyran ring of (-)-centrolobine and the C9-C19 tetrahydropyran ring of (+)-phorboxazole B. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.043

文献信息

• An asymmetric Maitland–Japp reaction: a highly enantioselective synthesis of tetrahydropyran-4-ones
  作者：Mudassar Iqbal、Nimesh Mistry、Paul A. Clarke

  DOI：10.1016/j.tet.2011.04.043

  日期：2011.7

  A highly enantioselective synthesis of functionalized tetrahydropyran-4-ones has been achieved by the development of a catalytic asymmetric Maitland-Japp reaction using Chan's diene as the nucleophile. This reaction has been used to synthesize the tetrahydropyran ring of (-)-centrolobine and the C9-C19 tetrahydropyran ring of (+)-phorboxazole B. (C) 2011 Elsevier Ltd. All rights reserved.