(1R,3aR,5R,7aR,1'R,4'S)-5,6,7,7a-tetrahydro-5-(diethylphosphonoacetoxy)-7a-methyl-1-(1',4',5'-trimethylhexyl)-3aH-indan-4-one | 1357600-68-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,3aR,5R,7aR,1'R,4'S)-5,6,7,7a-tetrahydro-5-(diethylphosphonoacetoxy)-7a-methyl-1-(1',4',5'-trimethylhexyl)-3aH-indan-4-one
• 英文别名: [(1R,3aR,5R,7aR)-1-[(2R,5S)-5,6-dimethylheptan-2-yl]-7a-methyl-4-oxo-2,3,3a,5,6,7-hexahydro-1H-inden-5-yl] 2-diethoxyphosphorylacetate
• CAS: 1357600-68-0
• 化学式: C₂₅H₄₅O₆P
• 分子量: 472.602
• InChiKey: XZNNHYJTCSSOAT-QYCMOUPQSA-N

物化性质

• 沸点：
  542.1±35.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,3aR,5R,7aR,1'R,4'S)-5,6,7,7a-tetrahydro-5-(diethylphosphonoacetoxy)-7a-methyl-1-(1',4',5'-trimethylhexyl)-3aH-indan-4-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以86%的产率得到(3aR,5aR,6R,8aR,1'R,4'S)-3a,3b,4,5,5a,7,8,8a-octahydro-5a-methyl-6-(1',4',5'-trimethylhexyl)-2H-indeno[5,4-b]furan-2-one
  参考文献：
  名称：

  Synthesis of two osteoclast-forming suppressors, demethylincisterol A3 and chaxine A

  摘要：

  The synthesis of two potent osteoclast-forming suppressing agents isolated from the Chinese mushroom Agrocybe chaxingu, demethylincisterol A(3) and chaxine A. was accomplished using ergocalciferol as the starting material. Our methodology for the synthesis of demethylincisterol A(3) and chaxine A featured the construction of a butenolide moiety by the intramolecular Horner-Wadsworth-Emmons reaction under Masamune-Roush conditions. This is the first reported synthesis of chaxine A. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.057
• 作为产物：
  描述：

  (1R,3AR,7AR)-1-(((2R,5R,E)-5,6-二甲基庚-3--烯-2-基)-7A-甲基八氢-4H-茚满-4-酮 在 吡啶 、 4-二甲氨基吡啶 、 platinum(IV) oxide 、 sodium tetrahydroborate 、 四氧化锇 、 水 、 氢气 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 、 N-甲基吗啉氧化物 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 29.75h， 生成 (1R,3aR,5R,7aR,1'R,4'S)-5,6,7,7a-tetrahydro-5-(diethylphosphonoacetoxy)-7a-methyl-1-(1',4',5'-trimethylhexyl)-3aH-indan-4-one
  参考文献：
  名称：

  Synthesis of two osteoclast-forming suppressors, demethylincisterol A3 and chaxine A

  摘要：

  The synthesis of two potent osteoclast-forming suppressing agents isolated from the Chinese mushroom Agrocybe chaxingu, demethylincisterol A(3) and chaxine A. was accomplished using ergocalciferol as the starting material. Our methodology for the synthesis of demethylincisterol A(3) and chaxine A featured the construction of a butenolide moiety by the intramolecular Horner-Wadsworth-Emmons reaction under Masamune-Roush conditions. This is the first reported synthesis of chaxine A. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.12.057

文献信息

• Synthesis of two osteoclast-forming suppressors, demethylincisterol A3 and chaxine A
  作者：Arata Yajima、Yuuma Kagohara、Keisuke Shikai、Ryo Katsuta、Tomoo Nukada

  DOI：10.1016/j.tet.2011.12.057

  日期：2012.2

  The synthesis of two potent osteoclast-forming suppressing agents isolated from the Chinese mushroom Agrocybe chaxingu, demethylincisterol A(3) and chaxine A. was accomplished using ergocalciferol as the starting material. Our methodology for the synthesis of demethylincisterol A(3) and chaxine A featured the construction of a butenolide moiety by the intramolecular Horner-Wadsworth-Emmons reaction under Masamune-Roush conditions. This is the first reported synthesis of chaxine A. (C) 2011 Elsevier Ltd. All rights reserved.