3β-acetoxy-2α,3α-epoxy-5α-cholestane | 7459-00-9

• 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-acetoxy-2α,3α-epoxy-5α-cholestane
• 英文别名: 3β-Acetoxy-2α,3α-epoxycholestane；3-acetoxy-2,3-epoxy-cholestane；3β-Acetoxy-2α,3α-epoxy-cholestan；[(1S,2S,4R,6R,8S,11R,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-6-yl] acetate
• CAS: 7459-00-9
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: WJIXKJVODIQPNM-FMSSLCCRSA-N

物化性质

• 沸点：
  498.6±28.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-2α,3α-epoxy-5α-cholestane 在 乙酸酐 、 三乙胺 作用下， 反应 2.0h， 以89%的产率得到2α-acetoxy-5α-cholestan-3-one
  参考文献：
  名称：

  2,3-官能化的胆甾烷和雄烷酮衍生物的新颖，有效的合成和抗真菌评价

  摘要：

  胆固醇和其他传统类固醇分子的合成修饰已成为探索和开发新型抗真菌剂的有前途的领域，尤其是在类固醇脂肪酸酯的开发方面。另外，2，3-官能化的类固醇也是具有潜在令人感兴趣的生物学性质的化合物，并且2，3-类固醇的适当官能化可以导致开发有效合成的类固醇的脂肪酸酯的结构单元。在这封信中，我们概述了合成2，3-官能化的胆甾烷和雄烷酮衍生物的新颖而有效的方法，并提出了它们对许多真菌物种的有希望的初步抗真菌活性。

  DOI：

  10.1016/j.bmcl.2010.10.044
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 甲基环氧丙烷 、 高氯酸 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 生成 3β-acetoxy-2α,3α-epoxy-5α-cholestane
  参考文献：
  名称：

  Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1

  摘要：

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.

  DOI：

  10.1021/jo00101a052

文献信息

• Reaction of bromo epoxides and acetoxy epoxides with amines
  作者：Alfred Hassner、Panayotis Catsoulacos

  DOI：10.1021/jo01278a007

  日期：1967.3
• Novel and efficient synthesis and antifungal evaluation of 2,3-functionalized cholestane and androstane derivatives
  作者：Branko S. Jursic、Sunil Kumar Upadhyay、Clinton C. Creech、Donna M. Neumann

  DOI：10.1016/j.bmcl.2010.10.044

  日期：2010.12

  to the development of efficient syntheses of building blocks for novel fatty-acid esters of steroids. In this Letter, we outline a novel and efficient approach to the synthesis of 2,3-functionalized cholestane and androstane derivatives and present their promising preliminary antifungal activities against a number of fungal species.

  胆固醇和其他传统类固醇分子的合成修饰已成为探索和开发新型抗真菌剂的有前途的领域，尤其是在类固醇脂肪酸酯的开发方面。另外，2，3-官能化的类固醇也是具有潜在令人感兴趣的生物学性质的化合物，并且2，3-类固醇的适当官能化可以导致开发有效合成的类固醇的脂肪酸酯的结构单元。在这封信中，我们概述了合成2，3-官能化的胆甾烷和雄烷酮衍生物的新颖而有效的方法，并提出了它们对许多真菌物种的有希望的初步抗真菌活性。
• Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1
  作者：Clayton H. Heathcock、Stephen C. Smith

  DOI：10.1021/jo00101a052

  日期：1994.11

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.