3,4-seco-cholest-5-ene-3,4-dioic acid | 434-11-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,4-seco-cholest-5-ene-3,4-dioic acid
• 英文别名: 3,4-Seco-cholest-5-en-3,4-disaeure；3.4-Seco-cholesten-(5)-disaeure-(3.4)；(3R,3aR,5aS,6R,9aS,9bS)-6-(2-carboxyethyl)-3a,6-dimethyl-3-[(2R)-6-methylheptan-2-yl]-2,3,4,5,5a,9,9a,9b-octahydro-1H-cyclopenta[a]naphthalene-7-carboxylic acid
• CAS: 434-11-7
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: QJUQBYMZJRWYDP-OLZFZNDLSA-N

物化性质

• 熔点：
  285 °C
• 沸点：
  563.8±23.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,4-seco-cholest-5-ene-3,4-dioic acid 在 氢氧化钾 、 potassium permanganate 作用下， 生成 7-oxo-3,4-seco-cholestene-(5)-dioic acid-(3,4)
  参考文献：
  名称：

  Cholesterol and Companions. II. Exhaustive Dichromate Oxidation

  摘要：

  DOI：

  10.1021/ja01114a002
• 作为产物：
  描述：

  cholesterol 在 次溴酸钾 作用下， 生成 3,4-seco-cholest-5-ene-3,4-dioic acid
  参考文献：
  名称：

  478.类固醇。第三部分 3-甲基-A-降胆固醇-3（5）-烯

  摘要：

  DOI：

  10.1039/jr9520002528

文献信息

• Structure – chiroptical properties relationship of cisoid enones with an α-methylenecyclopentanone unit
  作者：Jadwiga Frelek、Aleksandra Butkiewicz、Marcin Górecki、Ryszard K. Wojcieszczyk、Roman Luboradzki、Marcin Kwit、Michał F. Rode、Wojciech J. Szczepek

  DOI：10.1039/c4ra04991h

  日期：——

  In the present work, the validity of sector and helicity rules correlating the stereostructure of cis-enones containing the 2-methylenecyclopentanone unit with the sign of the nπ* Cotton effect (CE) observed in their electronic circular dichroism (ECD) spectra is assessed. To this end, a series of model steroid cis-enones with five-membered ketone rings was synthesized. To investigate the scope and limitations of existing rules a combination of ECD spectroscopy, X-ray analysis, and time-dependent density functional theory (TD-DFT) calculations were utilized. A comparison of the experimental ECD spectra with spectra simulated by the TD-DFT calculations gave a reasonable interpretation of the nπ* CE's observed in the 360–335 nm spectral range. The results suggest that the previously articulated rules are not applicable to the investigated compounds. On the basis of comprehensive analysis of collected data, a new rule correlating perfectly the structure of studied enones with the signs of their nπ* CE was proposed. This rule correlates directly the sign of the torsion angle “b” of the cyclopentanone ring of cis-enone with the sign of the nπ* CE.

  在本研究工作中，评估了与含有2-亚甲基环戊酮单元的顺式环烯酮的立体结构相关的扇区和螺旋规则的有效性，这些规则关联了它们在电子圆二色性(ECD)光谱中观察到的n→π* Cotton效应(CE)的符号。为此，合成了一系列具有五元酮环的模型甾体顺式环烯酮。为了探究现有规则的适用范围和局限性，采用了ECD光谱学、X射线分析和含时密度泛函理论(TD-DFT)计算相结合的方法。通过比较实验ECD光谱与由TD-DFT计算模拟的光谱，对在360-335 nm光谱范围内观察到的n→π* CE给出了合理的解释。结果表明，先前阐述的规则不适用于所研究的化合物。基于对收集数据的全面分析，提出了一条与所研究环烯酮结构完美关联的新规则，该规则直接关联顺式环烯酮的环戊酮环的扭转角“b”的符号与n→π* CE的符号。
• Gawronski,J.; Galat,A., Roczniki Chemii, 1975, vol. 49, p. 91 - 97
  作者：Gawronski,J.、Galat,A.

  DOI：——

  日期：——
• Diels; Abderhalden, Chemische Berichte, 1903, vol. 36, p. 3177,3181, 3182
  作者：Diels、Abderhalden

  DOI：——

  日期：——
• 79. The action of selenium dioxide on sterols and bile acids. Part III. Cholesterol
  作者：O. Rosenheim、W. W. Starling

  DOI：10.1039/jr9370000377

  日期：——
• Ultrastructural Localisation of Sialoadhesin (Siglec- 1) on Macrophages in Rodent Lymphoid Tissues
  作者：Inge L. Schadee-Eestermans、Elizabeth C.M. Hoefsmit、Marja Van De Ende、Paul R. Crocker、Timo K. Van Den Berg

  DOI：10.1016/s0171-2985(00)80036-4

  日期：2000.11

  In previous studies it has been demonstrated that sialoadhesin is a macrophage-restricted adhesion receptor for lymphocytes and myeloid cells. It is under normal circumstances expressed by subpopulations of macrophages in lymphoid and haemopoietic tissues. In this study different immunoelectronmicroscopical techniques are used to investigate the ultrastructural localisation of sialoadhesin within the lymph node and spleen of rodents. The results show that sialoadhesin is selectively expressed by a subset of macrophages in peripheral lymphoid tissues. Sialoadhesin was localised predominantly on the plasma membrane and in particular in areas of intimate contact with lymphocytes, thereby visualizing putative local interaction between these cells. Interestingly, sialoadhesin was also detected in intracellular vesicles that were apparently taken up by macrophages. These findings are consistent with the putative role of sialoadhesin in local cell-cell interactions in lymphoid tissues. Surprisingly, sialoadhesin was also found at contact points of macrophages with other macrophages, sinus-lining cells and reticulum cells, suggesting that sialoadhesin also mediates interactions with these cell types.