(4aR,10aR)-5,6,8-trimethoxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene | 24279-02-5

• 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: (4aR,10aR)-5,6,8-trimethoxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene
• CAS: 24279-02-5；60268-93-1
• 化学式: C₂₃H₃₆O₃
• 分子量: 360.537
• InChiKey: XGTHJDPAKPKRKK-WAIKUNEKSA-N

物化性质

• 沸点：
  468.2±45.0 °C(predicted)
• 密度：
  0.991±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4aR,10aR)-5,6,8-trimethoxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene 在 3,5-二甲基吡唑 、 2,4,6-三甲基吡啶 、 chromium(VI) oxide 、 18-冠醚-6 、 四丁基溴化铵 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 25.83h， 生成 benzyl (4aS,9S,9aS)-5,6,8-trimethoxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,9,9a-tetrahydro-2H-fluorene-9-carboxylate
  参考文献：
  名称：

  Divergent Total Synthesis of Taiwaniaquinones A and F and Taiwaniaquinols B and D

  摘要：

  A divergent approach was developed toward the total synthesis of taiwaniaquinoids. An advanced intermediate 5a with trans NB ring junction was concisely assembled by employing a Bi(OTf)(3)-catalyzed cationic cyclization and a Wolff-type ring contraction as key steps. This common intermediate was readily converted to racemic taiwaniaquinones A and F and taiwaniaquinols B and D, respectively.

  DOI：

  10.1021/ol400717h
• 作为产物：
  描述：

  在 bismuth(lll) trifluoromethanesulfonate 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 硝基甲烷 、 水 为溶剂， 反应 2.5h， 生成 (4aR,10aR)-5,6,8-trimethoxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene
  参考文献：
  名称：

  Divergent Total Synthesis of Taiwaniaquinones A and F and Taiwaniaquinols B and D

  摘要：

  A divergent approach was developed toward the total synthesis of taiwaniaquinoids. An advanced intermediate 5a with trans NB ring junction was concisely assembled by employing a Bi(OTf)(3)-catalyzed cationic cyclization and a Wolff-type ring contraction as key steps. This common intermediate was readily converted to racemic taiwaniaquinones A and F and taiwaniaquinols B and D, respectively.

  DOI：

  10.1021/ol400717h

文献信息

• A synthesis of the abietane diterpenoid quinone (±)-royleanone via maleoylcobalt technology.
  作者：Lanny S. Liebeskind、Ramakrishnan Chidambaram、Sanjay Nimkar、Dennis Liotta

  DOI：10.1016/s0040-4039(00)97454-9

  日期：——
• ENGLER, THOMAS A.;SAMPATH, UMASHANKER;NAGANATHAN, SRIRAM;VELDE, DAVID VAN+, J. ORG. CHEM., 54,(1989) N4, C. 1954
  作者：ENGLER, THOMAS A.、SAMPATH, UMASHANKER、NAGANATHAN, SRIRAM、VELDE, DAVID VAN+

  DOI：——

  日期：——
• LIEBESKIND, LANNY S.;CHIDAMBARAM, RAMAKRISHNAN;NIMKAR, SANJAY;LIOTTA, DEN+, TETRAHEDRON LETT., 31,(1990) N6, C. 3723-3726
  作者：LIEBESKIND, LANNY S.、CHIDAMBARAM, RAMAKRISHNAN、NIMKAR, SANJAY、LIOTTA, DEN+

  DOI：——

  日期：——