(3R)-3-Hydroxy-1-[(4S)-4-(1-methylethyl)-2-thioxo-3-thiazolidinyl]-4-penten-1-one | 790661-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (3R)-3-Hydroxy-1-[(4S)-4-(1-methylethyl)-2-thioxo-3-thiazolidinyl]-4-penten-1-one
• 英文别名: (3R)-3-hydroxy-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]pent-4-en-1-one
• CAS: 790661-42-6
• 化学式: C₁₁H₁₇NO₂S₂
• 分子量: 259.393
• InChiKey: QRJWZESGUWVTJK-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  40.54
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-methyl-2-(2-((tert-butoxycarbanylamino)methyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylate 、 (3R)-3-Hydroxy-1-[(4S)-4-(1-methylethyl)-2-thioxo-3-thiazolidinyl]-4-penten-1-one 在 三氟乙酸 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到methyl (4R)-2-[2-[[[(3R)-3-hydroxypent-4-enoyl]amino]methyl]-1,3-thiazol-4-yl]-4-methyl-5H-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and Activity of Largazole Analogues with Linker and Macrocycle Modification

  摘要：

  To characterize largazole's structural requirements for histone deacetylase (HDAC) inhibitory and anti proliferative activities, a series of analogues with modifications to the side chain or 16-membered macrocycle were prepared and biologically evaluated. Structure-activity relationships suggested that the four-atom linker between the macrocycle and octanoyl group in the side chain and the (S)-configuration at the C17 position are critical to repression of HDAC activity. However, the valine residue in the macrocycle can be replaced with alanine without significant loss of activity.

  DOI：

  10.1021/ol801532s
• 作为产物：
  描述：

  (R)-1-(4-异丙基-2-硫氧代噻唑啉-3-基)乙酮 、 丙烯醛 在 四氯化钛 、 鹰爪豆碱 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (3S)-3-hydroxy-1-[(4S)-4-propan-2-yl-2-sulfanylidene-1,3-thiazolidin-3-yl]pent-4-en-1-one 、 (3R)-3-Hydroxy-1-[(4S)-4-(1-methylethyl)-2-thioxo-3-thiazolidinyl]-4-penten-1-one
  参考文献：
  名称：

  Stereoselective aldol additions of titanium enolates of N-acetyl-4-isopropyl-thiazolidinethione

  摘要：

  The addition of chlorotitanium enolates of N-acetyl isopropyl thiazolidine-2-thione to aldehydes was investigated. The stereoselectivity of the aldol products was controlled by the number of equivalents of base added. The syn aldol product was obtained preferentially when 2 equiv of Lewis acid and 1 equiv of base were employed. The anti aldol product was obtained preferentially when 1 equiv of Lewis acid and 2 equiv of base were employed for unsaturated aldehydes. Unexpected results were found with hindered aldehydes when 2 equiv of base were employed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.008