3β-Acetoxy-24-norchola-5,17(20)-dien-16α-ol-23-oic acid δ-lactone | 75023-90-4

• 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-Acetoxy-24-norchola-5,17(20)-dien-16α-ol-23-oic acid δ-lactone
• 英文别名: 3-acetoxy-16α-hydroxy-24-norchola-5,17(20)-dien-23-oic acid δ-lactone
• CAS: 75023-90-4
• 化学式: C₂₅H₃₄O₄
• 分子量: 398.543
• InChiKey: HFXHBXHIANYHLW-KQAJCJRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3β-Acetoxy-24-norchola-5,17(20)-dien-16α-ol-23-oic acid δ-lactone 在 disodium hydrogenphosphate 、 potassium dihydrogenphosphate 、 葡萄糖 、 corn-steep liquor 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以50%的产率得到(4aS,4bR,6aS,10aR,11aS,11bS)-4b-Hydroxy-4a,6a,7-trimethyl-3,4,4a,4b,5,6,6a,8,10a,11,11a,11b,12,13-tetradecahydro-10-oxa-indeno[2,1-a]phenanthrene-2,9-dione
  参考文献：
  名称：

  Synthesis of 9α-hydroxysteroids by a Rhodococcus sp.

  摘要：

  9 alpha-Hydroxylation of delta 5-3 beta-hydroxysteroids (of androstane, pregnane, 24-nor- and 21,24-bisnorcholane groups) was carried out by a Rhodococcus sp., isolated from a petroleum-containing soil sample. A large number of the investigated steroids was transformed into 9 alpha-hydroxy-delta 4-3-ketones in satisfactory yields (50-90%) at high initial concentrations of the substrates (0.5-5.0 g/L). The influence of some structural features of the steroid molecule on the progress and effectiveness of the microbial transformation was also shown.

  DOI：

  10.1016/0039-128x(89)90002-0

文献信息

• Transformed steroids. 121. Synthesis of the ?-lactone of 3?-acetoxy-16?-hydroxy-6-oxo-24-nor-5?-chol-17(20)-en-23-oic acid
  作者：A. V. Kamernitskii、V. A. Krivoruchko、I. G. Reshetova、E. I. Chernoburova

  DOI：10.1007/bf00634732

  日期：——

  The synthesis of the Δ17(20)-16α analog of natural chiogralactone is described. Attempts to introduce a 6-oxo group directly into the δ-lactone proved unsuccessful, since the first stage — saponification — took place with the formation of three products: the 3-hydroxy-δ-lactone, the 3-hydroxy-Δ20(22)-lactone, and the 15,17(20)-dienoic acid. The synthesis of the desired compound was effected from the

  描述了天然 chiogralactone 的 Δ17(20)-16α 类似物的合成。将 6-氧代基团直接引入 δ-内酯的尝试被证明是不成功的，因为第一阶段——皂化——发生了三种产物：3-羟基-δ-内酯、3-羟基-Δ20（22 )-内酯和 15,17(20)-二烯酸。所需化合物的合成由 5,16-二烯酸的乙酯通过方案 3-乙酸酯→3-甲苯磺酸酯→6-羟基-3α,5α-环甾体→6-氧代-3α,5α-环甾体→6-oxo-5αH-δ-内酯。已经表明，3α,5α-环甾体δ-内酯中的环丙烷环在酸处理条件下极其稳定。
• Transformed steroids
  作者：A. V. Kamernitskii、V. A. Krivoruchko、I. G. Reshetova、B. M. Zolotarev

  DOI：10.1007/bf00958827

  日期：1980.6
• Biological activity of transformed steroids
  作者：A. V. Kamernitskii、I. G. Reshetova、E. I. Chernoburova、N. E. Voishvillo

  DOI：10.1007/bf00766682

  日期：1985.7