[(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-(2-chloroethyl)-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-11'-yl] carbamate | 616225-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: [(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-(2-chloroethyl)-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-11'-yl] carbamate
• CAS: 616225-50-4
• 化学式: C₁₈H₂₆ClNO₈
• 分子量: 419.859
• InChiKey: QSCFCLIXPOKVNW-XBADOFNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-(2-chloroethyl)-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-11'-yl] carbamate 在 吡啶 、 Rh₂(CF₃CONH)₄ 、 碘苯二乙酸 、 水 、 magnesium oxide 、 三乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 生成
  参考文献：
  名称：

  A Stereoselective Synthesis of (−)-Tetrodotoxin

  摘要：

  An asymmetric synthesis of the fugu fish poison, (-)-tetrodotoxin, is described. The route to this extraordinary target employs a number of unique transformations, foremost of which are two stereospecific C-H bond functionalization reactions. Accordingly, Rh-catalyzed carbene and nitrene C-H insertions facilitate rapid entry to the cyclohexane core of the natural product and make possible the late-stage installation of the tetrasubstituted carbinolamine center.

  DOI：

  10.1021/ja0368305
• 作为产物：
  描述：

  [(1'S,2'S,4S,6'S,8'R,11'S,12'R)-2,2,4',4'-tetramethyl-10'-oxo-12'-prop-2-enylspiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-11'-yl] 2,2-dimethylpropanoate 在 吡啶 、 sodium tetrahydroborate 、 sodium methylate 、 臭氧 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 [(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-(2-chloroethyl)-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-11'-yl] carbamate
  参考文献：
  名称：

  A Stereoselective Synthesis of (−)-Tetrodotoxin

  摘要：

  An asymmetric synthesis of the fugu fish poison, (-)-tetrodotoxin, is described. The route to this extraordinary target employs a number of unique transformations, foremost of which are two stereospecific C-H bond functionalization reactions. Accordingly, Rh-catalyzed carbene and nitrene C-H insertions facilitate rapid entry to the cyclohexane core of the natural product and make possible the late-stage installation of the tetrasubstituted carbinolamine center.

  DOI：

  10.1021/ja0368305

文献信息

• A Stereoselective Synthesis of (−)-Tetrodotoxin
  作者：Andrew Hinman、J. Du Bois

  DOI：10.1021/ja0368305

  日期：2003.9.1

  An asymmetric synthesis of the fugu fish poison, (-)-tetrodotoxin, is described. The route to this extraordinary target employs a number of unique transformations, foremost of which are two stereospecific C-H bond functionalization reactions. Accordingly, Rh-catalyzed carbene and nitrene C-H insertions facilitate rapid entry to the cyclohexane core of the natural product and make possible the late-stage installation of the tetrasubstituted carbinolamine center.