(1'R,2'S,4S,6'S,8'R,11'S,12'R)-11'-hydroxy-2,2,4',4'-tetramethyl-12'-prop-2-enylspiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-10'-one | 616225-49-1

• 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'R,2'S,4S,6'S,8'R,11'S,12'R)-11'-hydroxy-2,2,4',4'-tetramethyl-12'-prop-2-enylspiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-10'-one
• CAS: 616225-49-1
• 化学式: C₁₈H₂₆O₇
• 分子量: 354.4
• InChiKey: XTKTUDBCXBNGGQ-VXIVXGEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1'R,2'S,4S,6'S,8'R,11'S,12'R)-11'-hydroxy-2,2,4',4'-tetramethyl-12'-prop-2-enylspiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-10'-one 在 吡啶 、 sodium tetrahydroborate 、 臭氧 、 锌 作用下， 以 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
• 作为产物：
  描述：

  2,2-Dimethyl-propionic acid (3S,3aR,4S,5S,6R,7aS)-4,5,6-trihydroxy-6-hydroxymethyl-2-oxo-octahydro-benzofuran-3-yl ester 在 吡啶 、 copper(l) iodide 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 碘酰苯 、 二苯基二硒醚 、 硼烷-叔丁基胺 、 sodium methylate 、 四氯化钛 、 对甲苯磺酸 、 lead(II) chloride 、 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 、 氯苯 为溶剂， 反应 2.0h， 生成 (1'R,2'S,4S,6'S,8'R,11'S,12'R)-11'-hydroxy-2,2,4',4'-tetramethyl-12'-prop-2-enylspiro[1,3-dioxolane-4,7'-3,5,9-trioxatricyclo[6.3.1.02,6]dodecane]-10'-one
  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.