2-iodo-2,3-seco-17-oxa-5α-A-norandrostan-3-ol | 131768-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-iodo-2,3-seco-17-oxa-5α-A-norandrostan-3-ol
• CAS: 131768-40-6
• 化学式: C₁₇H₂₉IO₂
• 分子量: 392.321
• InChiKey: XSJLUSQPBWQZLN-FQMQPWHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-iodo-2,3-seco-17-oxa-5α-A-norandrostan-3-ol 在 吡啶 、 sodium iodide 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 117.0h， 生成 3-benzyl-3-aza-17-oxa-5α-androstane
  参考文献：
  名称：

  Transformation of epiandrosterone into 3-oxa-, 3-thia-, 3-selena-, and 3-aza-17-oxaandrostanes of the 5α series based on β-scission of alkoxyl radicals

  摘要：

  3-beta-Hydroxy-5-alpha-androstan-17-one was transformed into 17-oxa-5-alpha-androstan-3-beta-ol in five steps involving conversion of the 17-ketone via the corresponding lactol to its hypoiodite and thence a regioselective beta-scission under irradiation to give ring D seco iodoformate, from which the 17-oxasteroids were derived. Four bisheterosteroids 3,17-dioxa-5-alpha-androstane, 3-thia-17-oxa-5-alpha-androstane, 3-aza-17-oxa-5-alpha-androstane, and 3-selena-17-oxa-5-alpha-androstane) were synthesized from 17-oxa-5-alpha-androstan-3-beta-ol via 5, 8, 8, and 9 steps, respectively, involving a second regioselective beta-scission of an alkoxyl radical as the key step.

  DOI：

  10.1016/0039-128x(90)90059-k
• 作为产物：
  描述：

  Formic acid (3aS,5aS,6R,7R,9aR,9bS)-6-(2-iodo-ethyl)-3a,6-dimethyl-dodecahydro-naphtho[2,1-b]furan-7-ylmethyl ester 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以90%的产率得到2-iodo-2,3-seco-17-oxa-5α-A-norandrostan-3-ol
  参考文献：
  名称：

  Transformation of epiandrosterone into 3-oxa-, 3-thia-, 3-selena-, and 3-aza-17-oxaandrostanes of the 5α series based on β-scission of alkoxyl radicals

  摘要：

  3-beta-Hydroxy-5-alpha-androstan-17-one was transformed into 17-oxa-5-alpha-androstan-3-beta-ol in five steps involving conversion of the 17-ketone via the corresponding lactol to its hypoiodite and thence a regioselective beta-scission under irradiation to give ring D seco iodoformate, from which the 17-oxasteroids were derived. Four bisheterosteroids 3,17-dioxa-5-alpha-androstane, 3-thia-17-oxa-5-alpha-androstane, 3-aza-17-oxa-5-alpha-androstane, and 3-selena-17-oxa-5-alpha-androstane) were synthesized from 17-oxa-5-alpha-androstan-3-beta-ol via 5, 8, 8, and 9 steps, respectively, involving a second regioselective beta-scission of an alkoxyl radical as the key step.

  DOI：

  10.1016/0039-128x(90)90059-k