(1S,8aS)-1-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1-carbonitrile | 146205-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,8aS)-1-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1-carbonitrile
• 英文别名: (1S,8aS)-1-[tert-butyl(dimethyl)silyl]oxy-7-hydroxy-8a-methyl-6-oxo-3,4,7,8-tetrahydro-2H-naphthalene-1-carbonitrile
• CAS: 146205-63-2
• 化学式: C₁₈H₂₉NO₃Si
• 分子量: 335.519
• InChiKey: VCFHHXLSWSVWEP-XSRYCBBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,8aS)-1-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1-carbonitrile 在 sodium periodate 作用下， 以 水 、 叔丁醇 为溶剂， 生成 [(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-cyano-2-methyl-2-(2-oxo-ethyl)-cyclohex-(Z)-ylidene]-acetic acid methyl ester
  参考文献：
  名称：

  An enantioselective approach to ring a of taxol using the wieland-miescher ketone

  摘要：

  The selective protection of the S-(+)-enantiomer of the Wieland Miescher ketone (2) as the tertbutyldimethylsilyl-protected cyanohydrin 7 and the oxidative cleavage of an alpha-ketol 8 that was derived from 7 provided a model 10 for the A ring of the taxol (1) possessing the correct C-1 stereochemistry of taxol and functionality suitable for further elaboration.

  DOI：

  10.1016/s0040-4039(00)60056-4
• 作为产物：
  描述：

  (4'aS)-4',4'a,7',8'-tetrahydro-4'a-methylspiro<1,3-dithiolane-2,2'(3'H)-naphthalen>-5'(6'H)-one 在 thallium(I) nitrate 、 potassium carbonate 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 苯 为溶剂， 反应 68.0h， 生成 (1S,8aS)-1-(tert-Butyl-dimethyl-silanyloxy)-7-hydroxy-8a-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalene-1-carbonitrile
  参考文献：
  名称：

  An enantioselective approach to ring a of taxol using the wieland-miescher ketone

  摘要：

  The selective protection of the S-(+)-enantiomer of the Wieland Miescher ketone (2) as the tertbutyldimethylsilyl-protected cyanohydrin 7 and the oxidative cleavage of an alpha-ketol 8 that was derived from 7 provided a model 10 for the A ring of the taxol (1) possessing the correct C-1 stereochemistry of taxol and functionality suitable for further elaboration.

  DOI：

  10.1016/s0040-4039(00)60056-4

文献信息

• An enantioselective approach to ring a of taxol using the wieland-miescher ketone
  作者：Miroslaw Golinski、Sundar Vasudevan、Rey Floresca、Carolyn P. Brock、David S. Watt

  DOI：10.1016/s0040-4039(00)60056-4

  日期：1993.1

  The selective protection of the S-(+)-enantiomer of the Wieland Miescher ketone (2) as the tertbutyldimethylsilyl-protected cyanohydrin 7 and the oxidative cleavage of an alpha-ketol 8 that was derived from 7 provided a model 10 for the A ring of the taxol (1) possessing the correct C-1 stereochemistry of taxol and functionality suitable for further elaboration.