(2R,4aR,9aR)-7-(diethoxyphosphorylmethyl)-2,5-bis(methoxymethoxy)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene | 1069118-64-4

• 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-(diethoxyphosphorylmethyl)-2,5-bis(methoxymethoxy)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene
• CAS: 1069118-64-4
• 化学式: C₂₅H₄₁O₈P
• 分子量: 500.569
• InChiKey: VGBRZLZNOORQSJ-TZBSWOFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,4aR,9aR)-7-(diethoxyphosphorylmethyl)-2,5-bis(methoxymethoxy)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene 、 4-Methoxy-1-methyl-3-phenylindole-6-carbaldehyde 在 15-冠醚-5 、 sodium hydride 、 盐酸 、 水 作用下， 以 四氢呋喃 、 mineral oil 、 甲醇 为溶剂， 反应 2.0h， 以8%的产率得到(2R,4aR,9aR)-7-[2-(4-methoxy-1-methyl-3-phenylindol-6-yl)ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,5-diol
  参考文献：
  名称：

  [EN] SCHWEINFURTHIN ANALOGUES
  [FR] ANALOGUES DE SCHWEINFURTHINES

  摘要：

  本发明提供一种化合物，其化学式为(I)：其中R1-R5可以是规范中定义的任何值。这些化合物可用于治疗癌症和其他疾病。

  公开号：

  WO2013148584A1
• 作为产物：
  描述：

  在 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 1.58h， 生成 (2R,4aR,9aR)-7-(diethoxyphosphorylmethyl)-2,5-bis(methoxymethoxy)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene
  参考文献：
  名称：

  Synthesis and structure activity relationships of schweinfurthin indoles

  摘要：

  As part of a program to explore the biological activity of analogues of the natural schweinfurthins, a set of compounds has been prepared where an indole system can be viewed as a substitution for the resorcinol substructure of the schweinfurthin's D-ring. Twelve of these schweinfurthin indoles have been prepared and evaluated in the 60 cell line screen of the National Cancer Institute. While a range of activity has been observed, it is now clear that schweinfurthin indoles can demonstrate the intriguing pattern of activity associated with the natural stilbenes. In the best cases, these indole analogues display both potency and differential activity across the various cell lines comparable to the best resorcinol analogues. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.02.043

文献信息

• BF₃·Et₂O-Mediated Cascade Cyclizations: Synthesis of Schweinfurthins F and G
  作者：Nolan R. Mente、Jeffrey D. Neighbors、David F. Wiemer

  DOI：10.1021/jo800951q

  日期：2008.10.17

  total synthesis of the natural stilbene (+)-schweinfurthin G (8) has been accomplished through a sequence based on an efficient cationic cascade cyclization. This cascade process is initiated by Lewis acid promoted ring opening of an epoxide and terminated through a novel reaction with a phenolic oxygen "protected" as its MOM ether. Several Lewis acids have been examined for their ability to induce

  天然二苯乙烯 (+)-schweinfurthin G (8) 的全合成已通过基于有效阳离子级联环化的序列完成。该级联过程由路易斯酸促进环氧化物的开环引发，并通过与作为其 MOM 醚“保护”的酚氧发生新反应而终止。已经检查了几种路易斯酸诱导这种新反应的能力，发现 BF3 x Et2O 是最有效的。在这些条件下唯一的主要副产物是预期的仲醇被发现为其 MOM 醚衍生物（例如，30）。虽然这种副产物可以通过水解转化为原始的目标化合物，它还可以用作受保护的醇，以允许在不使仲醇脱水的情况下制备苄基膦酸酯 (43)。所得的膦酸酯用于与代表目标化合物右半部分的醛的 Horner-Wadsworth-Emmons 缩合反应，这是对先前基于右半膦酸酯和左半醛缩合的研究的补充。
• SCHWEINFURTHIN ANALOGUES
  申请人：University of Iowa Research Foundation

  公开号：US20150045404A1

  公开（公告）日：2015-02-12

  The invention provides a compound of formula (I): wherein R 1 -R 5 have any of the values defined in the specification. The compounds are useful for the treatment of cancer and other diseases.

  本发明提供了一个化合物的公式(I)：其中R1-R5具有规范中定义的任何值。这些化合物对于治疗癌症和其他疾病是有用的。
• US9428493B2
  申请人：——

  公开号：US9428493B2

  公开（公告）日：2016-08-30
• Synthesis and structure activity relationships of schweinfurthin indoles
  作者：John G. Kodet、John A. Beutler、David F. Wiemer

  DOI：10.1016/j.bmc.2014.02.043

  日期：2014.4

  As part of a program to explore the biological activity of analogues of the natural schweinfurthins, a set of compounds has been prepared where an indole system can be viewed as a substitution for the resorcinol substructure of the schweinfurthin's D-ring. Twelve of these schweinfurthin indoles have been prepared and evaluated in the 60 cell line screen of the National Cancer Institute. While a range of activity has been observed, it is now clear that schweinfurthin indoles can demonstrate the intriguing pattern of activity associated with the natural stilbenes. In the best cases, these indole analogues display both potency and differential activity across the various cell lines comparable to the best resorcinol analogues. (C) 2014 Elsevier Ltd. All rights reserved.
• [EN] SCHWEINFURTHIN ANALOGUES<br/>[FR] ANALOGUES DE SCHWEINFURTHINES
  申请人：UNIV IOWA RES FOUND

  公开号：WO2013148584A1

  公开（公告）日：2013-10-03

  The invention provides a compound of formula (I): wherein R1-R5 have any of the values defined in the specification. The compounds are useful for the treatment of cancer and other diseases.

  本发明提供一种化合物，其化学式为(I)：其中R1-R5可以是规范中定义的任何值。这些化合物可用于治疗癌症和其他疾病。