(3R,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one | 959461-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (3R,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one
• 英文别名: (3R,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydrocyclopenta[b][1]benzofuran-1-one
• CAS: 959461-41-7
• 化学式: C₂₆H₂₄O₆
• 分子量: 432.473
• InChiKey: YBPDGDRCEOEXIY-VANUSSGQSA-N

物化性质

• 沸点：
  603.7±55.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydrocyclopentabenzofuran-1-one 、 (3R,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 、 氯化铵 、 sodium L-tartrate 、 potassium L-tartrate 作用下， 以 乙腈 、 水 为溶剂， 反应 3.5h， 以66%的产率得到rocaglaol
  参考文献：
  名称：

  WO2007/139749

  摘要：

  公开号：
• 作为产物：
  描述：

  trimethoxy cyclopenta[bc]benzopyran 在 水 、 sodium methylate 、 lithium chloride 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 12.33h， 生成 (3R,3aR,8bR)-8b-Hydroxy-6,8-dimethoxy-3a-(4-methoxy-phenyl)-3-phenyl-2,3,3a,8b-tetrahydro-benzo[b]cyclopenta[d]furan-1-one
  参考文献：
  名称：

  手性布朗斯台德酸介导的对映选择性光环加成反应：Rocaglamides 的不对称合成

  摘要：

  罗卡格酸甲酯和相关天然产物罗卡格莱胺和罗卡格洛尔的对映选择性合成概述。该方法涉及由手性布朗斯台德酸 (TADDOL) 促进的对映选择性 [3 + 2] 光环加成反应，以提供 aglain 前体，然后是酮醇转移/还原序列到 rocaglate 核心。

  DOI：

  10.1021/ja062621j

文献信息

• Davey, Andrew E.; Schaeffer, Marcel J.; Taylor, Richard J. K., Journal of the Chemical Society. Perkin transactions I, 1992, # 20, p. 2657 - 2666
  作者：Davey, Andrew E.、Schaeffer, Marcel J.、Taylor, Richard J. K.

  DOI：——

  日期：——
• Asymmetric Synthesis of Rocaglamides via Enantioselective Photocycloaddition Mediated by Chiral Bronsted Acids
  申请人：Porco, JR. John A.

  公开号：US20090299081A1

  公开（公告）日：2009-12-03

  The present invention provides a new strategies for the synthesis of compounds of the rocaglamide family and related natural products. The synthetic approach generally involves photochemical generation of an oxidopyrylium species from a 3-hydroxychromone derivative followed by an enantioselective 1,3-dipolar cycloaddition of the oxidopyrylium species to a dipolarophile in the presence of a TADDOL derivative. This approach can be used for the formation of adducts containing an aglain core structure. Methods of the conversion of aglain core structures to aglain, rocaglamide and forbaglin ring systems are also provided. The present invention also relates to the use of rocaglamide/aglain/forbaglin derivatives for the manufacture of medicaments for use in the treatment of cancer or cancerous conditions, disorders associated with cellular hyperproliferation, or NF-κB-dependent conditions.
• ASYMMETRIC SYNTHESIS OF ROCAGLAMIDES VIA ENANTIOSELECTIVE PHOTOCYCLOADDITION MEDIATED BY CHIRAL BRONSTED ACIDS
  申请人：Porco, JR. John A.

  公开号：US20120238766A1

  公开（公告）日：2012-09-20

  The present invention provides a new strategies for the synthesis of compounds of the rocaglamide family and related natural products. The synthetic approach generally involves photochemical generation of an oxidopyrylium species from a 3-hydroxychromone derivative followed by an enantioselective 1,3-dipolar cycloaddition of the oxidopyrylium species to a dipolarophile in the presence of a TADDOL derivative. This approach can be used for the formation of adducts containing an aglain core structure. Methods of the conversion of aglain core structures to aglain, rocaglamide and forbaglin ring systems are also provided. The present invention also relates to the use of rocaglamide/aglain/forbaglin derivatives for the manufacture of medicaments for use in the treatment of cancer or cancerous conditions, disorders associated with cellular hyperproliferation, or NF-κB-dependent conditions.
• US8137509B2
  申请人：——

  公开号：US8137509B2

  公开（公告）日：2012-03-20
• US8404088B2
  申请人：——

  公开号：US8404088B2

  公开（公告）日：2013-03-26