(E)-5-(tert-butylthio)pent-2-enal | 1338230-03-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-5-(tert-butylthio)pent-2-enal
• CAS: 1338230-03-7
• 化学式: C₉H₁₆OS
• 分子量: 172.291
• InChiKey: CZTXQZSHTPDCBI-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-5-(tert-butylthio)pent-2-enal 、 (R)-3-乙酰基-4-异丙基-1,3-噻唑烷-2-硫酮 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以50%的产率得到(3S,4E)-7-(tert-butylthio)-3-hydroxy-1-((4R)-4-isopropyl-2-thioxothiazolidin-3-yl)hept-4-en-1-one
  参考文献：
  名称：

  Largazole and Analogues with Modified Metal-Binding Motifs Targeting Histone Deacetylases: Synthesis and Biological Evaluation

  摘要：

  The histone deacetylase inhibitor largazole 1 was synthesized by a convergent approach that involved several efficient and high yielding single pot multistep protocols. Initial attempts using tert-butyl as thiol protecting group proved problematic, and synthesis was accomplished by switching to the trityl protecting group. This synthetic protocol provides a convenient approach to many new largazole analogues. Three side chain analogues with multiple heteroatoms for chelation with Zn2+ were synthesized, and their biological activities were evaluated. They were less potent than largazole 1 in growth inhibition of HCT116 colon carcinoma cell line and in inducing increases in global H3 acetylation. Largazole 1 and the three side chain analogues had no effect on HDAC6, as indicated by the lack of increased acetylation of alpha-tubulin.

  DOI：

  10.1021/jm200432a
• 作为产物：
  描述：

  6-(2-(tert-butylthio)ethyl)-6H-1,3-diox-4-ene 以 甲苯 为溶剂， 反应 1.83h， 以0.211 g的产率得到(E)-5-(tert-butylthio)pent-2-enal
  参考文献：
  名称：

  Largazole and Analogues with Modified Metal-Binding Motifs Targeting Histone Deacetylases: Synthesis and Biological Evaluation

  摘要：

  The histone deacetylase inhibitor largazole 1 was synthesized by a convergent approach that involved several efficient and high yielding single pot multistep protocols. Initial attempts using tert-butyl as thiol protecting group proved problematic, and synthesis was accomplished by switching to the trityl protecting group. This synthetic protocol provides a convenient approach to many new largazole analogues. Three side chain analogues with multiple heteroatoms for chelation with Zn2+ were synthesized, and their biological activities were evaluated. They were less potent than largazole 1 in growth inhibition of HCT116 colon carcinoma cell line and in inducing increases in global H3 acetylation. Largazole 1 and the three side chain analogues had no effect on HDAC6, as indicated by the lack of increased acetylation of alpha-tubulin.

  DOI：

  10.1021/jm200432a