(2R,4aR,9aR)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,5-diol | 1263362-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R,4aR,9aR)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,5-diol
• CAS: 1263362-09-9
• 化学式: C₁₈H₂₆O₄
• 分子量: 306.402
• InChiKey: POVLOQGGGITYFJ-IIDMSEBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4aR,9aR)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,5-diol 在 甲醇 、 sodium tetrahydroborate 、 potassium permanganate 、 cerium(III) chloride 、 四丙基高钌酸铵 、 水 、 碳酸氢钠 、 potassium carbonate 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 52.66h， 生成 (6R,7S,8aR,10aR)-4,6,7-tris(methoxymethoxy)-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthene-2-carbaldehyde
  参考文献：
  名称：

  First total synthesis of (+)-vedelianin, a potent antiproliferative agent

  摘要：

  The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (25,3R,4aR,9aR)-isomer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.137
• 作为产物：
  描述：

  (2R,4aR,9aR)-5-(methoxymethoxy)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol 在 甲醇 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 75.0h， 生成 (2R,4aR,9aR)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,5-diol
  参考文献：
  名称：

  First total synthesis of (+)-vedelianin, a potent antiproliferative agent

  摘要：

  The total synthesis of (+)-vedelianin has been accomplished in 18 steps from vanillin. Preparation of a key intermediate in nonracemic form through a Shi epoxidation has allowed determination of the absolute stereochemistry of the natural product as the (25,3R,4aR,9aR)-isomer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.137

文献信息

• Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A
  作者：Joseph J. Topczewski、John G. Kodet、David F. Wiemer

  DOI：10.1021/jo1022102

  日期：2011.2.4

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.