(1S,3aS,4S,7aS)-1-((tert-butyldimethylsilyl)oxy)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-7a-methyl-1,2,3,3a,4,7a-hexahydro-5H-inden-5-one | 1041183-83-8

• 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: (1S,3aS,4S,7aS)-1-((tert-butyldimethylsilyl)oxy)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-7a-methyl-1,2,3,3a,4,7a-hexahydro-5H-inden-5-one
• CAS: 1041183-83-8
• 化学式: C₂₄H₄₆O₃Si₂
• 分子量: 438.798
• InChiKey: NVADSVNIHAPLHE-RSKVWTTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,3aS,4S,7aS)-1-((tert-butyldimethylsilyl)oxy)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-7a-methyl-1,2,3,3a,4,7a-hexahydro-5H-inden-5-one 在 四(三苯基膦)钯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.66h， 生成 methyl (1S,3aS,7aS)-1-((tert-butyldimethylsilyl)oxy)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-7a-methyl-2,3,3a,7a-tetrahydro-1H-indene-5-carboxylate
  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：

  (S)-(+)-2,3,7,7A-四氢-7A-甲基-1H-茚-1,5(6H)-二酮 在 咪唑 、 sodium tetrahydroborate 、 nickel chloride hexahydrate 、 palladium diacetate 、 sodium hydride 、 六甲基二硅氮烷 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 14.33h， 生成 (1S,3aS,4S,7aS)-1-((tert-butyldimethylsilyl)oxy)-4-(2-((tert-butyldimethylsilyl)oxy)ethyl)-7a-methyl-1,2,3,3a,4,7a-hexahydro-5H-inden-5-one
  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

• A Concise Synthesis of the Pentacyclic Framework of Cortistatins
  作者：Shuji Yamashita、Kentaro Iso、Masahiro Hirama

  DOI：10.1021/ol8012099

  日期：2008.8.21

  An efficient synthesis of the pentacyclic framework of cortistatins has been developed. The key strategy comprises assembly of the A- and the CD-ring fragments by Knoevenagel reaction, facile formation of the pyran ring via electrocyclization, and construction of the seven-membered B-ring by radical addition to an alpha,beta-unsaturated ketone.