(2R,4aR,9aR)-5-(hydroxymethyl)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol | 1263362-07-7

• 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)-5-(hydroxymethyl)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol
• CAS: 1263362-07-7
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: KBSPBLKSEWHCKU-GPMSIDNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 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)-5-(hydroxymethyl)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol 在 manganese(IV) oxide 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 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：

  Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

  摘要：

  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.

  DOI：

  10.1021/jo1022102
• 作为产物：
  描述：

  2-Bromo-4-(methoxymethyl)-1-(phenylmethoxymethoxy)benzene 在 正丁基锂 、 四甲基乙二胺 、 三氟化硼乙醚 作用下， 以 hexanes 、 乙醚 、 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 38.38h， 生成 (2R,4aR,9aR)-5-(hydroxymethyl)-7-(methoxymethyl)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-2-ol
  参考文献：
  名称：

  Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

  摘要：

  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.

  DOI：

  10.1021/jo1022102

文献信息

• Relevance of the C-5 position to schweinfurthin induced cytotoxicity
  作者：Joseph J. Topczewski、Michael P. Callahan、John G. Kodet、Jery D. Inbarasu、Nolan R. Mente、John A. Beutler、David F. Wiemer

  DOI：10.1016/j.bmc.2011.10.034

  日期：2011.12

  The schweinfurthins are an intriguing group of anti-proliferative agents that display low nanomolar activities against several cell types, including the human-derived glioblastoma cell line SF-295, but have little impact on other cell lines even at micromolar concentrations. This activity has inspired the synthesis of seven of the natural schweinfurthins, all with the correct absolute stereochemistry, and a variety of analogues designed to probe different facets of the pharmacophore. Reported herein is the synthesis of several new schweinfurthin analogues varied at the C-5 position along with data on their biological activity in the NCI 60 cell-line assay. (C) 2011 Elsevier Ltd. All rights reserved.