1-[3-[[(3β,5α,7α,24S)-7-(methoxymethoxy)-24-hydroxycholestan-3-yl]amino]propyl]-2-pyrrolidinone | 952312-07-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 1-[3-[[(3β,5α,7α,24S)-7-(methoxymethoxy)-24-hydroxycholestan-3-yl]amino]propyl]-2-pyrrolidinone
• 英文别名: 1-[3-[[(3S,5R,7R,8R,9S,10S,13R,14S,17R)-17-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-7-(methoxymethoxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]propyl]pyrrolidin-2-one
• CAS: 952312-07-1
• 化学式: C₃₆H₆₄N₂O₄
• 分子量: 588.915
• InChiKey: RPWROTZXGNSGTL-DGVJBXLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[3-[[(3β,5α,7α,24S)-7-(methoxymethoxy)-24-hydroxycholestan-3-yl]amino]propyl]-2-pyrrolidinone 在 吡啶 、 盐酸 、 pyridine-SO3 complex 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-[3-[[(3β,5α,7α,24S)-7,24-bis(sulfooxy)cholestan-3-yl]amino]propyl]-2-pyrrolidinone disodium salt
  参考文献：
  名称：

  Details of the Structure Determination of the Sulfated Steroids PSDS and PADS:  New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

  摘要：

  [GRAPHICS]The discovery of two new components of the migratory pheromone used by sea lamprey to guide adults to spawning grounds was recently reported. These hold promise for use in a pheromone-based control program for this species, an invasive pest in the Great Lakes. Details of the structure determination of these steroidal bis-sulfates [petromyzosterol disulfate (PSDS, 2) and petromyzonamine disulfate (PADS, 3)] are described here. Pattern matching of H-1 NMR data was particularly valuable. This involved comparison of spectra of the natural samples of 2 and 3 with those of appropriate steroidal analogues [e.g., petromyzonol sulfate (PS, 1, a previously known sea lamprey bile acid derivative that is a third component of the migratory pheromone), cholesterol sulfate (6), and squalamine (8)] and model compounds containing the unprecedented aminolactam substructure present in 3. The logic underlying the iterative analyses used is presented.

  DOI：

  10.1021/jo070957l
• 作为产物：
  描述：

  1-(3-氨基丙基)-2-吡咯烷酮 在 sodium tetrahydroborate 、 3 A molecular sieve 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 1-[3-[[(3β,5α,7α,24S)-7-(methoxymethoxy)-24-hydroxycholestan-3-yl]amino]propyl]-2-pyrrolidinone
  参考文献：
  名称：

  Details of the Structure Determination of the Sulfated Steroids PSDS and PADS:  New Components of the Sea Lamprey (Petromyzon marinus) Migratory Pheromone

  摘要：

  [GRAPHICS]The discovery of two new components of the migratory pheromone used by sea lamprey to guide adults to spawning grounds was recently reported. These hold promise for use in a pheromone-based control program for this species, an invasive pest in the Great Lakes. Details of the structure determination of these steroidal bis-sulfates [petromyzosterol disulfate (PSDS, 2) and petromyzonamine disulfate (PADS, 3)] are described here. Pattern matching of H-1 NMR data was particularly valuable. This involved comparison of spectra of the natural samples of 2 and 3 with those of appropriate steroidal analogues [e.g., petromyzonol sulfate (PS, 1, a previously known sea lamprey bile acid derivative that is a third component of the migratory pheromone), cholesterol sulfate (6), and squalamine (8)] and model compounds containing the unprecedented aminolactam substructure present in 3. The logic underlying the iterative analyses used is presented.

  DOI：

  10.1021/jo070957l

文献信息

• Details of the Structure Determination of the Sulfated Steroids PSDS and PADS:  New Components of the Sea Lamprey (<i>Petromyzon </i><i>marinus</i>) Migratory Pheromone
  作者：Thomas R. Hoye、Vadims Dvornikovs、Jared M. Fine、Kari R. Anderson、Christopher S. Jeffrey、David C. Muddiman、Feng Shao、Peter W. Sorensen、Jizhou Wang

  DOI：10.1021/jo070957l

  日期：2007.9.1

  [GRAPHICS]The discovery of two new components of the migratory pheromone used by sea lamprey to guide adults to spawning grounds was recently reported. These hold promise for use in a pheromone-based control program for this species, an invasive pest in the Great Lakes. Details of the structure determination of these steroidal bis-sulfates [petromyzosterol disulfate (PSDS, 2) and petromyzonamine disulfate (PADS, 3)] are described here. Pattern matching of H-1 NMR data was particularly valuable. This involved comparison of spectra of the natural samples of 2 and 3 with those of appropriate steroidal analogues [e.g., petromyzonol sulfate (PS, 1, a previously known sea lamprey bile acid derivative that is a third component of the migratory pheromone), cholesterol sulfate (6), and squalamine (8)] and model compounds containing the unprecedented aminolactam substructure present in 3. The logic underlying the iterative analyses used is presented.