4α,5α-methano-5β-cholestan-3-one | 2602-40-6

• 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: 4α,5α-methano-5β-cholestan-3-one
• 英文别名: (1S,2R,6S,8R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]pentacyclo[9.7.0.02,8.06,8.012,16]octadecan-5-one
• CAS: 2602-40-6
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: IMSFSSVAFPMINE-OOWWKEHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4α,5α-methano-5β-cholestan-3-one 以96%的产率得到4α,5α-methano-5β-cholestan-3β-ol
  参考文献：
  名称：

  4,5-Cyclopropanocholestan-3β-ol Substrates for Cholesterol Oxidase and Their ¹H NMR Assignments

  摘要：

  We have assayed 4,5-cyclopropanocholestan-3-ols and 4,5-cyclopropanocholestan-3-ones and tested them as substrates and inhibitors of cholesterol oxidase. The 4,5-cyclopropanocholestan-3 beta-ols (alpha and beta) are substrates of cholesterol oxidase that are converted to their respective ketones 1000-fold more slowly than cholesterol. The induced ring-current effects of a cyclopropane ring are clearly illustrated in the H-1 NMR spectra of these sterols. These shielding effects are dramatic because of the rigidity of the steroid backbone. Assignments of the H-1 resonances of the A, B, and cyclopropyl rings of the sterols have been made using DQF-COSY and NOESY experiments. We have assigned the upheld multiplet at approximately 0.5 ppm to H-6 alpha in both isomers. H-6 alpha is Shielded by the cyclopropyl sigma bond. H-6 beta is deshielded by the cyclopropane ring and appears at approximately 2.0 ppm in both isomers.

  DOI：

  10.1021/jo9706537
• 作为产物：
  描述：

  5-tosyloxymethyl-5α-cholestan-3-one ethylene acetal 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 生成 4α,5α-methano-5β-cholestan-3-one
  参考文献：
  名称：

  桥接类固醇的合成。I.类固醇，具有双环[3.2.1]辛环环，其是叶绿体类型。

  摘要：

  以 5α-氰基胆甾烷-3-酮为起始原料，通过三种途径合成了 A 环上具有双环 [3.其中，将氰基转化为乙酰基，然后进行环化的合成路线最为可取。

  DOI：

  10.1248/cpb.16.867

文献信息

• Yates, Peter; Winnik, Francoise M., Canadian Journal of Chemistry, 1981, vol. 59, p. 1641 - 1650
  作者：Yates, Peter、Winnik, Francoise M.

  DOI：——

  日期：——
• Joska, Jiri; Fajkos, Jan, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 6, p. 1850 - 1859
  作者：Joska, Jiri、Fajkos, Jan

  DOI：——

  日期：——
• Fajkos, Jan; Joska, Jiri; Zajicek, Jaroslav, Collection of Czechoslovak Chemical Communications, 1983, vol. 48, # 12, p. 3455 - 3473
  作者：Fajkos, Jan、Joska, Jiri、Zajicek, Jaroslav

  DOI：——

  日期：——