A-nortestosterone acetate | 1162-89-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: A-nortestosterone acetate
• 英文别名: 17β-hydroxy-4-norandrost-3-en-2-one acetate；A-Nor-testosteron-acetat；O-Acetyl-A-nor-testosteron；17β-Acetoxy-2-oxo-A-nor-androsten-(3)；2-Oxo-17β-acetoxy-Δ³-A-nor-androsten；[(3aR,3bS,5aS,6S,8aS,8bR)-3a,5a-dimethyl-2-oxo-3b,4,5,6,7,8,8a,8b,9,10-decahydro-3H-indeno[5,4-e]inden-6-yl] acetate
• CAS: 1162-89-6
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: KTVDMDPBIWRLOT-RABCQHRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  A-nortestosterone acetate 在 sodium hydroxide 作用下， 生成 A-nortestosterone
  参考文献：
  名称：

  A-类固醇的研究。二。17-β-羟基-A-norandrost-3（5）-烯-1,2-二酮与几种试剂的反应。

  摘要：

  研究了 17β-hydroxy-A-norandrost-3(5)-ene-1, 2-dione (Ia) 及其 17-propionate (Ib) 与几种试剂的反应。用乙酸锌或液氨锂处理 I 后，只还原了 C1-羰基，得到 1β，17β-二羟基-A-去甲雄甾-3(5)-烯-2-酮（II）。相反，I 与羰基试剂在常规条件下反应，得到的相应衍生物仅在 C2-羰基上与试剂缩合。氢化锂铝或硼氢化钠还原 I 后，可得到在 C-2 处与 1β- 羟基缩合的乙二醇 (IV) 和 (V)。

  DOI：

  10.1248/cpb.13.156
• 作为产物：
  描述：

  17β-Acetoxy-A-nor-5α-androstan-2-on 在 palladium on barium sulfate 2,3,5-三甲基吡啶 、 氢溴酸 、 氢气 、 溴 作用下， 以 溶剂黄146 、 xylene 为溶剂， 生成 A-nortestosterone acetate
  参考文献：
  名称：

  Hanna,R. et al., Bulletin de la Societe Chimique de France, 1961, p. 1209 - 1212

  摘要：

  DOI：

文献信息

• Holland, Herbert L.; Chenchaiah, P. Chinna, Canadian Journal of Chemistry, 1985, vol. 63, p. 1127 - 1131
  作者：Holland, Herbert L.、Chenchaiah, P. Chinna

  DOI：——

  日期：——
• Tandem Carbon-Radical Peroxidation-Addition to Carbonyl Groups Reaction. A New Synthesis of Steroidal .beta.-Peroxy Lactones
  作者：Alicia Boto、Rosendo Hernandez、Ernesto Suarez、Carmen Betancor、Maria S. Rodriguez

  DOI：10.1021/jo00130a020

  日期：1995.12

  A mild and efficient synthesis of beta-peroxy lactones by alkoxy radical beta-fragmentation reaction of gamma-hydroxy carbonyl compounds is described. Steroidal models 5-hydroxy-4-nor-3-oxa-5 alpha-cholestan-2-one (1), 5-hydroxy-5 alpha-cholestan-2-one (2), and 5,17 beta-dihydroxy-4-nor-5 alpha-androstan-2-one 17-acetate (3) were synthesized to test the present methodology. These substrates are subjected to photolysis with visible light in the presence of (diacetoxyiodo)benzene, lead tetraacetate, or HgO, I-2, and molecular oxygen to generate the corresponding alkoxy radical. The fragmentation of this radical results in the carbon radical which is trapped by molecular oxygen in the key step to generate a peroxy radical. Intramolecular addition of this peroxy radical to the carbonyl group present in the molecule is followed by beta-fragmentation to yield the peroxy lactone radical. Subsequent trapping of this radical results in stable peroxy lactone. In all cases, regiospecific beta-fragmentations and stereoselective peroxidation at C-10 radical were observed. This operationally simple multistep radical procedure permitted us to synthesize steroidal beta-peroxy lactones 8, 12, and 15 in moderate to good yields.
• Synthese der 2,5-Diole des A-nor-5α-Androstan-17β-ols und A-nor-5β-Androstan-17β-ols
  作者：L. Lábler、Ch. Tamm

  DOI：10.1002/hlca.19720550313

  日期：1972.4.20

  AbstractThe synthesis of A‐nor‐5β‐androstane‐2α,5,17β‐triol (8), A‐nor‐5β‐androstane‐2β,5,17β‐triol (10), A‐nor‐5α‐androstane‐2β,5,17β‐triol (20), A‐nor‐5α‐androstane‐2β,5,17β‐triol (22) and of their 17‐O‐benzoyl derivatives is described, using A‐nor‐testosterone (1) as starting material.
• Hanna,R. et al., Bulletin de la Societe Chimique de France, 1961, p. 1209 - 1212
  作者：Hanna,R. et al.

  DOI：——

  日期：——
• Studies on A-Norsteroids. II. Reactions of 17β-Hydroxy-A-norandrost-3(5)-ene-1, 2-dione with Several Reagents
  作者：Keiji Yoshida、Tokuo Kubota

  DOI：10.1248/cpb.13.156

  日期：——

  Reactions of 17β-hydroxy-A-norandrost-3(5)-ene-1, 2-dione (Ia) and its 17-propionate (Ib) with several reagents have been examined. Treatment of I with zinc-acetic acid or lithium-liquid ammonia resulted in the reduction of only the C1-carbonyl group giving 1β, 17β-dihydroxy-A-norandrost-3(5)-en-2-one (II). On the contrary, reaction of I with carbonyl reagents in the usual condition afforded the corresponding derivatives which were condensed at only the C2-carbonyl group with the reagents. Lithium aluminum hydride or sodium borohydride reduction of I gave the glycols, (IV) and (V), epimeric at C-2 with the 1β-hydroxyl group.

  研究了 17β-hydroxy-A-norandrost-3(5)-ene-1, 2-dione (Ia) 及其 17-propionate (Ib) 与几种试剂的反应。用乙酸锌或液氨锂处理 I 后，只还原了 C1-羰基，得到 1β，17β-二羟基-A-去甲雄甾-3(5)-烯-2-酮（II）。相反，I 与羰基试剂在常规条件下反应，得到的相应衍生物仅在 C2-羰基上与试剂缩合。氢化锂铝或硼氢化钠还原 I 后，可得到在 C-2 处与 1β- 羟基缩合的乙二醇 (IV) 和 (V)。