[(3S,3aS,9bS)-7-methoxy-3a-methyl-1,2,3,4,5,6,9,9b-octahydrocyclopenta[a]naphthalen-3-yl]oxy-tert-butyl-dimethylsilane | 1276688-52-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [(3S,3aS,9bS)-7-methoxy-3a-methyl-1,2,3,4,5,6,9,9b-octahydrocyclopenta[a]naphthalen-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1276688-52-8
• 化学式: C₂₁H₃₆O₂Si
• 分子量: 348.601
• InChiKey: JRXLIHZVYSDLTK-ZJOUEHCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [(3S,3aS,9bS)-7-methoxy-3a-methyl-1,2,3,4,5,6,9,9b-octahydrocyclopenta[a]naphthalen-3-yl]oxy-tert-butyl-dimethylsilane 在 盐酸 、 lead(IV) tetraacetate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 苯 为溶剂， 反应 33.0h， 生成 methyl 3-[(1S,3aS,7aS)-1-[tert-butyl(dimethyl)silyl]oxy-5-formyl-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl]propanoate
  参考文献：
  名称：

  Total Synthesis of Cortistatins A and J

  摘要：

  This paper describes the details of our synthetic studies on the marine steroidal alkaloids cortistatins A and J. The key features of our strategy include (i) an efficient Knoevenagel/electrocyclic strategy to couple the diketone and the CD-ring fragment, (ii) a chemoselective radical cyclization to construct the oxabicyclo[3.2.1]octene B-ring system, (iii) a highly stereocontrolled installation of the isoquinoline unit, and (iv) a late-stage functionalization of the A-ring.

  DOI：

  10.1021/jo2002616
• 作为产物：
  描述：

  3-methoxy-7-[(3S)-4-methyl-3-phenylmethoxypent-4-enyl]bicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile 在 咪唑 、 正丁基锂 、 乙醇 、 氨 、 sodium 、 lithium 、 叔丁醇 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成 [(3S,3aS,9bS)-7-methoxy-3a-methyl-1,2,3,4,5,6,9,9b-octahydrocyclopenta[a]naphthalen-3-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Total Synthesis of Cortistatins A and J

  摘要：

  This paper describes the details of our synthetic studies on the marine steroidal alkaloids cortistatins A and J. The key features of our strategy include (i) an efficient Knoevenagel/electrocyclic strategy to couple the diketone and the CD-ring fragment, (ii) a chemoselective radical cyclization to construct the oxabicyclo[3.2.1]octene B-ring system, (iii) a highly stereocontrolled installation of the isoquinoline unit, and (iv) a late-stage functionalization of the A-ring.

  DOI：

  10.1021/jo2002616

文献信息

• Total Synthesis of Cortistatins A and J
  作者：Shuji Yamashita、Kentaro Iso、Kazuki Kitajima、Masafumi Himuro、Masahiro Hirama

  DOI：10.1021/jo2002616

  日期：2011.4.15

  This paper describes the details of our synthetic studies on the marine steroidal alkaloids cortistatins A and J. The key features of our strategy include (i) an efficient Knoevenagel/electrocyclic strategy to couple the diketone and the CD-ring fragment, (ii) a chemoselective radical cyclization to construct the oxabicyclo[3.2.1]octene B-ring system, (iii) a highly stereocontrolled installation of the isoquinoline unit, and (iv) a late-stage functionalization of the A-ring.