1,1'-[3,3'-disulfanediylbis(propane-3,1-diyl)]bis(3-methyl-4-tetradecyl-1H-pyrrole-2,5-dione) | 1416854-80-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,1'-[3,3'-disulfanediylbis(propane-3,1-diyl)]bis(3-methyl-4-tetradecyl-1H-pyrrole-2,5-dione)
• 英文别名: 1,1′-[3,3′-disulfanediylbis(propane-3,1-diyl)]bis(3-methyl-4-tetradecyl-1H-pyrrole-2,5-dione)
• CAS: 1416854-80-2
• 化学式: C₄₄H₇₆N₂O₄S₂
• 分子量: 761.23
• InChiKey: JXIDRTTYLQOGDS-UHFFFAOYSA-N

物化性质

• 沸点：
  797.2±45.0 °C(Predicted)
• 密度：
  1.024±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  52.0
• 可旋转键数：
  35.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  74.76
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1,1'-[3,3'-disulfanediylbis(propane-3,1-diyl)]bis(3-methyl-4-tetradecyl-1H-pyrrole-2,5-dione) 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以94%的产率得到毛酚酸A酸酐
  参考文献：
  名称：

  Novel route to chaetomellic acid A and analogues: Serendipitous discovery of a more competent FTase inhibitor

  摘要：

  A new practical route to chaetomellic acid A (ACA), based on the copper catalysed radical cyclization (RC) of (Z)-3-(2,2-dichloropropanoyl)-2-pentadecylidene-1,3-thiazinane, is described. Remarkably, the process entailed: (i) a one-pot preparation of the intermediate N-alpha-perchloroacyl-2-(Z)-alkyliden-1,3-thia-zinanes starting from N-(3-hydroxypropyl)palmitamide, (ii) a two step smooth transformation of the RC products into ACA and (iii) only one intermediate chromatographic purification step. The method offers a versatile approach to the preparation of ACA analogues, through the synthesis of an intermediate maleic anhydride with a vinylic group at the end of the aliphatic tail, a function that can be transformed through a thiol-ene coupling. Serendipitously, the disodium salt of 2-(9-(butylthio)nonyl)-3-methylmaleic acid, that we prepared as a representative sulfurated ACA analogue, was a more competent FTase inhibitor than ACA. This behaviour was analysed by a molecular docking study. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.034
• 作为产物：
  描述：

  在 吡啶 、 四甲基乙二胺 、 sodium carbonate 、 copper(l) chloride 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 63.0h， 生成 1,1'-[3,3'-disulfanediylbis(propane-3,1-diyl)]bis(3-methyl-4-tetradecyl-1H-pyrrole-2,5-dione)
  参考文献：
  名称：

  Novel route to chaetomellic acid A and analogues: Serendipitous discovery of a more competent FTase inhibitor

  摘要：

  A new practical route to chaetomellic acid A (ACA), based on the copper catalysed radical cyclization (RC) of (Z)-3-(2,2-dichloropropanoyl)-2-pentadecylidene-1,3-thiazinane, is described. Remarkably, the process entailed: (i) a one-pot preparation of the intermediate N-alpha-perchloroacyl-2-(Z)-alkyliden-1,3-thia-zinanes starting from N-(3-hydroxypropyl)palmitamide, (ii) a two step smooth transformation of the RC products into ACA and (iii) only one intermediate chromatographic purification step. The method offers a versatile approach to the preparation of ACA analogues, through the synthesis of an intermediate maleic anhydride with a vinylic group at the end of the aliphatic tail, a function that can be transformed through a thiol-ene coupling. Serendipitously, the disodium salt of 2-(9-(butylthio)nonyl)-3-methylmaleic acid, that we prepared as a representative sulfurated ACA analogue, was a more competent FTase inhibitor than ACA. This behaviour was analysed by a molecular docking study. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.034