dihydromirabazole C | 155158-73-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚氨硫酯类
• 英文名称: dihydromirabazole C
• 英文别名: (4S)-4-[(4S)-4-(4,5-dihydro-1,3-thiazol-2-yl)-4-methyl-5H-1,3-thiazol-2-yl]-4-methyl-2-[(4R)-4-methyl-2-propan-2-yl-5H-1,3-thiazol-4-yl]-5H-1,3-thiazole
• CAS: 155158-73-9
• 化学式: C₁₈H₂₆N₄S₄
• 分子量: 426.695
• InChiKey: ACKRXJWYGAYWPE-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  dihydromirabazole C 在 nickel(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以50%的产率得到(-)-mirabazole C
  参考文献：
  名称：

  Revision of the stereostructure of mirabazole C

  摘要：

  The stereostructure of mirabazole C is revised to 11 on the basis of total synthesis.

  DOI：

  10.1016/s0040-4039(00)76223-x
• 作为产物：
  描述：

  N-(2-methylpropionyl)-S-benzyl-(S)-2-methylcysteinyl-S-benzyl-(R)-methylcysteinyl-S-benzyl-(R)-methylcysteine N-((benzylthio)ethyl)amide 在 氨 、 sodium 、 四氯化钛 、 氯化铵 作用下， 生成 dihydromirabazole C
  参考文献：
  名称：

  Revision of the stereostructure of mirabazole C

  摘要：

  The stereostructure of mirabazole C is revised to 11 on the basis of total synthesis.

  DOI：

  10.1016/s0040-4039(00)76223-x

文献信息

• Convergent Synthesis of (−)-Mirabazole C Using a Chloroimidazolidium Coupling Reagent, CIP
  作者：Kenichi Akaji、Naohiro Kuriyama、Yoshiaki Kiso

  DOI：10.1021/jo952285h

  日期：1996.1.1

  Convergent synthesis of (-)-mirabazole C (1), a tetra thiazoline/thiazole alkaloid isolated from blue-green alga, has been described. The successive thiazoline rings of (-)-mirabazole C were formed by a single-step cyclization mediated by TiCl4 treatment of tripeptide amide 4. Convergent synthesis of the key intermediate 33 derived from three a-methylcysteine residues was first achieved using a newly developed coupling reagent, 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP). The effectiveness of CIP for the coupling of alpha,alpha-dialkyl amino acids and the reaction pathway of the activation were clarified by the syntheses of model peptides containing an alpha,alpha-dimethylamino acid. A practical method of asymmetric synthesis of 2-methylcysteine by alkylation of 2,4-cis-oxazolidinone 23 has also been described.