16α-acetoxypregn-4-ene-9α,21-diol-17α-thiol-3,20-dione 20-carborthoxyhydrazone | 147091-64-3

• 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: 16α-acetoxypregn-4-ene-9α,21-diol-17α-thiol-3,20-dione 20-carborthoxyhydrazone
• CAS: 147091-64-3
• 化学式: C₂₆H₃₈N₂O₇S
• 分子量: 522.663
• InChiKey: URTWXUNZSKOJPF-UTNQALFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  134.52
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  丙酮 、 16α-acetoxypregn-4-ene-9α,21-diol-17α-thiol-3,20-dione 20-carborthoxyhydrazone 在 高氯酸 作用下， 以 甲醇 为溶剂， 反应 144.0h， 以58%的产率得到pregn-4-ene-9α,16α,21-triol-17α-thiol-3,20-dione 16α,17α-acetonide
  参考文献：
  名称：

  Transformed steroids. 193. Synthesis of 16?,17?-isopropylidene derivatives of pregn-4-ene-9?,16?,17?,21-tetraol-3,20-dione and its 17?-thioanalog

  摘要：

  A study was carried out on the pathways for the transformation of 16alpha,17alpha-epoxypregn-4-ene-9alpha,21-diol-3,20-dione to give 16alpha,17alpha-isopropylidene derivatives of pregn-4-ene-9alpha,16alpha,17alpha,21-tetraol-3,20-dione and its 17alpha-thioanalog. The key step in this pathway is the cis-cleavage of the 20-carboethoxyhydrazone of this epoxide by acetic and thioacetic acids and subsequent condensation of the products formed with acetone. This pathway is an efficient approach to the synthesis of the 16alpha,17alpha-dioxolane derivative and is equally efficient for preparation of the thioanalog, namely, 16alpha,17alpha-isopropylidenepregn-4-ene-9alpha,16alpha,21-triol-17alpha-thiol-3,20-dione, which has already been synthesized by an alternative method.

  DOI：

  10.1007/bf00863832
• 作为产物：
  描述：

  16α,17α-epoxypregn-4-ene-9α,21-diol-3,20-dione 在 2-羟基环己-2,5-二烯-1,4-二酮 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 25.5h， 生成 16α-acetoxypregn-4-ene-9α,21-diol-17α-thiol-3,20-dione 20-carborthoxyhydrazone
  参考文献：
  名称：

  Transformed steroids. 193. Synthesis of 16?,17?-isopropylidene derivatives of pregn-4-ene-9?,16?,17?,21-tetraol-3,20-dione and its 17?-thioanalog

  摘要：

  A study was carried out on the pathways for the transformation of 16alpha,17alpha-epoxypregn-4-ene-9alpha,21-diol-3,20-dione to give 16alpha,17alpha-isopropylidene derivatives of pregn-4-ene-9alpha,16alpha,17alpha,21-tetraol-3,20-dione and its 17alpha-thioanalog. The key step in this pathway is the cis-cleavage of the 20-carboethoxyhydrazone of this epoxide by acetic and thioacetic acids and subsequent condensation of the products formed with acetone. This pathway is an efficient approach to the synthesis of the 16alpha,17alpha-dioxolane derivative and is equally efficient for preparation of the thioanalog, namely, 16alpha,17alpha-isopropylidenepregn-4-ene-9alpha,16alpha,21-triol-17alpha-thiol-3,20-dione, which has already been synthesized by an alternative method.

  DOI：

  10.1007/bf00863832