[4aR-(4aα,6aβ,10aα,10bβ)]-2-bromo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-4a,7,7,10a-tetramethyl-1H-naphtho[2,1-b]pyran-3-carboxaldehyde | 890026-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: [4aR-(4aα,6aβ,10aα,10bβ)]-2-bromo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-4a,7,7,10a-tetramethyl-1H-naphtho[2,1-b]pyran-3-carboxaldehyde
• 英文别名: (4aR,6aS,10aS,10bR)-2-bromo-4a,7,7,10a-tetramethyl-1,5,6,6a,8,9,10,10b-octahydrobenzo[f]chromene-3-carbaldehyde
• CAS: 890026-20-7
• 化学式: C₁₈H₂₇BrO₂
• 分子量: 355.315
• InChiKey: PZOBFTMZNGKFFE-CIRFHOKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [4aR-(4aα,6aβ,10aα,10bβ)]-2-bromo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-4a,7,7,10a-tetramethyl-1H-naphtho[2,1-b]pyran-3-carboxaldehyde 在 四(三苯基膦)钯 manganese(IV) oxide 、 sodium tetrahydroborate 、 copper(l) iodide 、 氰化钠 、 溶剂黄146 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 3-[(4aR,6aS,10aS,10bR)-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-3-(hydroxymethyl)-4a,7,7,10a-tetramethyl-1H-naphtho[2,1-b]pyran-2-yl]-2,6-pyridinedimethanol
  参考文献：
  名称：

  Synthesis of ent-Thallusin

  摘要：

  three-step route from sclareol oxide (6) to bromo ester 4 in 53% overall yield was achieved using the efficient oxidation of an allylic bromide to an enal with bis(2,4,6-trimethylpyridine)silver(l) hexafluorophosphate in DMSO. Stille coupling of bromo ester 4 with stannylpyridine 5 gave the trimethyl ester of ent-thallusin in 54-92% yield by the stoichiometric conversion of 4 to a vinyl palladium intermediate prior to the addition of 5 to the reaction.

  DOI：

  10.1021/ol0605777
• 作为产物：
  描述：

  [4aR-(4aα,6aβ,10aα,10bβ)]-2-bromo-3-(bromomethyl)-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-4a,7,7,10a-tetramethyl-1H-naphtho[2,1-b]pyran 在 bis(2,4,6-trimethylpyridine)silver(I) hexafluorophosphate 、 二甲基亚砜 作用下， 反应 5.0h， 以87%的产率得到[4aR-(4aα,6aβ,10aα,10bβ)]-2-bromo-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-4a,7,7,10a-tetramethyl-1H-naphtho[2,1-b]pyran-3-carboxaldehyde
  参考文献：
  名称：

  Synthesis of ent-Thallusin

  摘要：

  three-step route from sclareol oxide (6) to bromo ester 4 in 53% overall yield was achieved using the efficient oxidation of an allylic bromide to an enal with bis(2,4,6-trimethylpyridine)silver(l) hexafluorophosphate in DMSO. Stille coupling of bromo ester 4 with stannylpyridine 5 gave the trimethyl ester of ent-thallusin in 54-92% yield by the stoichiometric conversion of 4 to a vinyl palladium intermediate prior to the addition of 5 to the reaction.

  DOI：

  10.1021/ol0605777

文献信息

• Synthesis of <i>e</i><i>nt</i>-Thallusin
  作者：Xiaolei Gao、Yoshihide Matsuo、Barry B. Snider

  DOI：10.1021/ol0605777

  日期：2006.5.1

  three-step route from sclareol oxide (6) to bromo ester 4 in 53% overall yield was achieved using the efficient oxidation of an allylic bromide to an enal with bis(2,4,6-trimethylpyridine)silver(l) hexafluorophosphate in DMSO. Stille coupling of bromo ester 4 with stannylpyridine 5 gave the trimethyl ester of ent-thallusin in 54-92% yield by the stoichiometric conversion of 4 to a vinyl palladium intermediate prior to the addition of 5 to the reaction.