tert-butyl N-[(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-ethenyl-11'-hydroxy-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-1'-yl]carbamate | 616225-52-6

• 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: tert-butyl N-[(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-ethenyl-11'-hydroxy-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-1'-yl]carbamate
• CAS: 616225-52-6
• 化学式: C₂₂H₃₃NO₉
• 分子量: 455.505
• InChiKey: LADOXQVLFLLMRL-BKQNLDFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-ethenyl-11'-hydroxy-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-1'-yl]carbamate 在 水 、 三乙胺 、 mercury dichloride 作用下， 以 二氯甲烷 、 乙腈 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：

  [(1S)-1-[(3'aS,4R,4'S,7'aS)-2,2,2',2'-tetramethyl-5'-methylidene-6'-oxospiro[1,3-dioxolane-4,7'-4,7a-dihydro-3aH-1,3-benzodioxole]-4'-yl]-2-(dimethylamino)-2-oxoethyl] 2,2-dimethylpropanoate 在 吡啶 、 sodium tetrahydroborate 、 copper(l) iodide 、 Rh₂(CF₃CONH)₄ 、 碘苯二乙酸 、 硼烷-叔丁基胺 、 sodium methylate 、 magnesium oxide 、 臭氧 、 锌 、 三甲基乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 氯苯 、 苯 为溶剂， 反应 2.0h， 生成 tert-butyl N-[(1'S,2'S,4S,6'S,8'R,11'S,12'R)-12'-ethenyl-11'-hydroxy-2,2,4',4'-tetramethyl-10'-oxospiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-1'-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.