3β-<(tetrahydropyran-2-yl)oxy>-7-oxo-cholest-5-ene | 164120-23-4

• 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: 3β-<(tetrahydropyran-2-yl)oxy>-7-oxo-cholest-5-ene
• 英文别名: 3β-[(tetrahydropyran-2-yl)oxy]-7-oxo-cholest-5-ene；3β-((Ξ)-tetrahydropyran-2-yloxy)-cholest-5-en-7-one；3β-((Ξ)-Tetrahydropyran-2-yloxy)-cholest-5-en-7-on；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-3-(oxan-2-yloxy)-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• CAS: 164120-23-4
• 化学式: C₃₂H₅₂O₃
• 分子量: 484.763
• InChiKey: JBNKMIVUWXRCOY-SXAYHAFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-<(tetrahydropyran-2-yl)oxy>-7-oxo-cholest-5-ene 在 吡啶 、 lithium aluminium tetrahydride 、 sodium azide 、 4-甲基苯磺酸吡啶 、 L-Selectride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 124.25h， 生成 7β-aminocholesterol
  参考文献：
  名称：

  Elkihel; Gelin; Letourneux, Arzneimittel-Forschung/Drug Research, 1995, vol. 45, # 2, p. 190 - 194

  摘要：

  DOI：
• 作为产物：
  描述：

  胆固醇 在 吡啶 、 chromium(VI) oxide 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 生成 3β-<(tetrahydropyran-2-yl)oxy>-7-oxo-cholest-5-ene
  参考文献：
  名称：

  Elkihel; Gelin; Letourneux, Arzneimittel-Forschung/Drug Research, 1995, vol. 45, # 2, p. 190 - 194

  摘要：

  DOI：

文献信息

• Greenhalgh et al., Journal of the Chemical Society, 1952, p. 2380,2382
  作者：Greenhalgh et al.

  DOI：——

  日期：——
• Synthesis of spermidinylcholestanol and spermidinylcholesterol, squalamine analogues
  作者：Bassima Choucair、Michel Dherbomez、Cristos Roussakis、Laïla El Kihel

  DOI：10.1016/j.tet.2004.09.055

  日期：2004.12

  Several novel squalamine-related polyaminosterols are reported. The synthesis of 7alpha-N-[3N-(4-aminobutyl)aminopropyl]aminocholestanol I, 6alpha-N-[3N-(4-aminobutyl)aminopropyl]aminocholestanol II, 7alpha and 7beta-N-[3N-(4-aminobutyl)aminopropyl]aminocholesterol (III and IV), was accomplished from cholesterol, they provide the first examples in which spermidine is introduced in the B steroidal ring. These molecules showed comparable antibacteria and fungi activities to squalamine, and were cytotoxic on a human non-small cell bronchopulmonary carcinoma line (NSCLC-N6). Therefore, these molecules with antibiotic and cytotoxic activities are promising for immune-compromised patients in cancer chemotherapy. (C) 2004 Elsevier Ltd. All fights reserved.
• An Effective Method for Allylic Oxidation of Δ⁵-Steroids Using <i>tert</i>-Butyl Hydroperoxide
  作者：Yuancheng Li、Xianghong Wu、Tae Bum Lee、Eleanor K. Isbell、Edward J. Parish、Anne E. V. Gorden

  DOI：10.1021/jo902637k

  日期：2010.3.5

  An allylic oxidation method for Delta(5)-steroids using TBHP as oxidant with a 2-quinoxalinol salen Cu(II) complex as catalyst is reported. A variety of Delta(5)-steroidal substrates are selectively oxidized to the corresponding enones. Excellent yields are achieved (up to 99% under optimized conditions) while significantly reducing reaction times required as compared to other current methods.
• Stereoselective synthesis of 7α- and 7β-aminocholestanol as potent fungicidal drugs
  作者：S Fouace、L El kihel、M Dherbomez、Y Letourneux

  DOI：10.1016/s0960-894x(01)00609-6

  日期：2001.12

  Potentially lymphotropic 7 alpha- and 7 beta -aminocholestanol were stereo selectively synthesized. In vitro bioassay studies have shown that these fungicidal lipidic derivatives possess strong antifungal activity against Candida spp resistant strains to amphotericin B, 5-fluorocytosine and azoles. (C) 2001 Elsevier Science Ltd. All rights reserved.