5-[[(3aR,6aS)-3a-methyl-2,5,6,6a-tetrahydrofuro[2,3-d][1,3]thiazol-3-yl]methyl]-2-methylpyrimidin-4-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-[[(3aR,6aS)-3a-methyl-2,5,6,6a-tetrahydrofuro[2,3-d][1,3]thiazol-3-yl]methyl]-2-methylpyrimidin-4-amine
• 化学式: C₁₂H₁₈N₄OS
• 分子量: 266.367
• InChiKey: MZTDYOPZSKAKCL-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[[(3aR,6aS)-3a-methyl-2,5,6,6a-tetrahydrofuro[2,3-d][1,3]thiazol-3-yl]methyl]-2-methylpyrimidin-4-amine 在 sodium tetrahydroborate 、 borax buffer 作用下， 以 甲醇 为溶剂， 以75%的产率得到3-[(4-氨基-2-甲基-5-嘧啶基)甲基]-4-甲基-5-噻唑烷乙醇
  参考文献：
  名称：

  The Correct Structures of “Dihydrothiamine”. Resolution of a Long-Standing Controversy

  摘要：

  Reduction of thiamin (1) by a borohydride in water first gives bicyclic perhydrofuro[2,3-d]thiazole 3, Heating 3 in water generates fused tricyclic pyrimido[4,5-d]thiazolo[3,4-a]pyrimidine 4. X-ray crystal structures indicate the stereocenters are cis in 3 and cis-cis in 4, The kinetics of reduction of both 3 and 4 to tetrahydrothiamin 5 by additional aqueous borohydride show that 3 is the kinetic product of the reduction of 1 while 4 is the thermodynamic product produced from 3 in an acid-catalyzed ring-opening ring-closing isomerization process. Several structural assignments of ''dihydrothiamine'' presented some 40 years ago are incorrect, Subsequent reports based on the incorrect structures need to be reinterpreted.

  DOI：

  10.1021/jo970782n
• 作为产物：
  描述：

  thiamin chloride hydrochloride 在 sodium hydroxide 、 sodium trimethoxyborohydride 作用下， 以 甲醇 、 水 为溶剂， 以60.1%的产率得到5-[[(3aR,6aS)-3a-methyl-2,5,6,6a-tetrahydrofuro[2,3-d][1,3]thiazol-3-yl]methyl]-2-methylpyrimidin-4-amine
  参考文献：
  名称：

  The Correct Structures of “Dihydrothiamine”. Resolution of a Long-Standing Controversy

  摘要：

  Reduction of thiamin (1) by a borohydride in water first gives bicyclic perhydrofuro[2,3-d]thiazole 3, Heating 3 in water generates fused tricyclic pyrimido[4,5-d]thiazolo[3,4-a]pyrimidine 4. X-ray crystal structures indicate the stereocenters are cis in 3 and cis-cis in 4, The kinetics of reduction of both 3 and 4 to tetrahydrothiamin 5 by additional aqueous borohydride show that 3 is the kinetic product of the reduction of 1 while 4 is the thermodynamic product produced from 3 in an acid-catalyzed ring-opening ring-closing isomerization process. Several structural assignments of ''dihydrothiamine'' presented some 40 years ago are incorrect, Subsequent reports based on the incorrect structures need to be reinterpreted.

  DOI：

  10.1021/jo970782n

文献信息

• The Correct Structures of “Dihydrothiamine”. Resolution of a Long-Standing Controversy
  作者：John A. Zoltewicz、Carlton D. Dill、Khalil A. Abboud

  DOI：10.1021/jo970782n

  日期：1997.10.1

  Reduction of thiamin (1) by a borohydride in water first gives bicyclic perhydrofuro[2,3-d]thiazole 3, Heating 3 in water generates fused tricyclic pyrimido[4,5-d]thiazolo[3,4-a]pyrimidine 4. X-ray crystal structures indicate the stereocenters are cis in 3 and cis-cis in 4, The kinetics of reduction of both 3 and 4 to tetrahydrothiamin 5 by additional aqueous borohydride show that 3 is the kinetic product of the reduction of 1 while 4 is the thermodynamic product produced from 3 in an acid-catalyzed ring-opening ring-closing isomerization process. Several structural assignments of ''dihydrothiamine'' presented some 40 years ago are incorrect, Subsequent reports based on the incorrect structures need to be reinterpreted.