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 | 1276688-54-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 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
• CAS: 1276688-54-0
• 化学式: C₂₁H₃₆O₄Si
• 分子量: 380.6
• InChiKey: WZQJRKKPBDCSKT-WFXMLNOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  间苯三酚 、 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 在 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 反应 8.0h， 生成 methyl 3-[(3S,3aS,11aS,11bR)-3-[tert-butyl(dimethyl)silyl]oxy-7,9-dihydroxy-3a-methyl-1,2,3,4,5,11b-hexahydrocyclopenta[c]xanthen-11a-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：

  (3S,3aS,9bS)-3-[tert-butyl(dimethyl)silyl]oxy-3a-methyl-2,3,4,5,6,8,9,9b-octahydro-1H-cyclopenta[a]naphthalen-7-one 在 lead(IV) tetraacetate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 32.5h， 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

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.