三烯 | 4642-95-9

• 物质功能分类: 天然产物 - 甾体化合物
• 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
• 中文名称: 三烯
• 中文别名: 雌-4,9,11-三烯-3,17-二酮
• 英文名称: Trendione
• 英文别名: estra-4,9,11-triene-3,17-dione；17-ketotrenbolone；13β-methyl-gona-4,9,11-triene-3,17-dione；(8S,13S,14S)-13-methyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthrene-3,17-dione
• CAS: 4642-95-9
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: KBSXJBBFQODDTQ-RYRKJORJSA-N

物化性质

• 熔点：
  140℃
• 沸点：
  489.4±45.0 °C(Predicted)
• 密度：
  1.19
• 溶解度：
  DMF：30mg/mL； DMF:PBS(pH 7.2)(1:1)：0.5 mg/ml； DMSO：20mg/mL；乙醇：10mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三烯 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 以55%的产率得到
  参考文献：
  名称：

  Synthesis and SAR study of novel pseudo-steroids as potent and selective progesterone receptor antagonists

  摘要：

  Synthesis of novel 7-pseudo-steroids 1c has been achieved from trenbolone 3 via an efficient 14 step sequence with overall yields of 10-15%. Various substitutions were incorporated at both the aromatic side chain as well as the D ring. The orientation of aromatic side chain at C10 plays a crucial role for progesterone receptor (PR) activity. Compound 2a (T47D = 1 nM) with -NMe2 para to the aromatic group along with spirofurane groups in the D ring was the optimal substitution. All compounds were also evaluated for glucocorticoid receptor (GR) antagonist activities in vivo in a rat and found efficacious in uterine complement C3 assay via the oral route of administrations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.095
• 作为产物：
  描述：

  群勃龙 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 三烯
  参考文献：
  名称：

  Synthesis and SAR study of novel pseudo-steroids as potent and selective progesterone receptor antagonists

  摘要：

  Synthesis of novel 7-pseudo-steroids 1c has been achieved from trenbolone 3 via an efficient 14 step sequence with overall yields of 10-15%. Various substitutions were incorporated at both the aromatic side chain as well as the D ring. The orientation of aromatic side chain at C10 plays a crucial role for progesterone receptor (PR) activity. Compound 2a (T47D = 1 nM) with -NMe2 para to the aromatic group along with spirofurane groups in the D ring was the optimal substitution. All compounds were also evaluated for glucocorticoid receptor (GR) antagonist activities in vivo in a rat and found efficacious in uterine complement C3 assay via the oral route of administrations. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.01.095

文献信息

• A new route to 19-substituted steroids from 19-nor steroids: Sigmatropic [3,3] and [2,3] rearrangements revisited
  作者：D. Lesuisse、F. Canu、B. Tric

  DOI：10.1016/s0040-4020(01)85569-1

  日期：1994.1

  Sigmatropic [3,3] and [2,3] rearrangements of 11-substituted estradienedione derivatives gave rise to new 19-substituted androstenedione analogs.

  11-取代的雌二烯酮衍生物的σ[3,3]和[2,3]重排产生了新的19-取代的雄烯二酮类似物。
• 一种四烯雌酮的合成方法
  申请人：厦门欧瑞捷生物科技有限公司

  公开号：CN106946961B

  公开（公告）日：2019-08-06

  本发明公开了一种四烯雌酮的合成方法。先在醇溶剂中，于0‑25℃条件下加入酸A和化合物M，升至30‑90℃反应5‑24小时后降至室温，并蒸出溶剂；加入四氢呋喃，于‑10‑10℃加入上述所得产物，并滴加CH2CHCH2MgX，随后升至25‑60℃反应2‑5小时，再降温到0℃以下，滴加酸B调pH＝1‑3，再升温到60℃反应5小时；搅拌使分层，上层用无水硫酸钠干燥，浓缩，再放入5℃以下冷冻；重结晶即得到四烯雌酮。本发明对其进行一锅法制备四烯雌酮，所需原料易得，工艺简单且环境友好，成本低，产率高，特别适合于工业生产。
• Gonatriene derivatives and process for preparing them
  申请人：MITSUBISHI KASEI CORPORATION

  公开号：EP0231671B1

  公开（公告）日：1990-08-16
• Degradation of Synthetic Androgens 17α- and 17β-Trenbolone and Trendione in Agricultural Soils
  作者：Bushra Khan、Linda S. Lee、Stephen A. Sassman

  DOI：10.1021/es702690p

  日期：2008.5

  17 beta-trenbolone acetate (TBA) is a synthetic androgenic steroid hormone administered as a subcutaneous implant for growth promotion in beef cattle. TBA is converted metabolically to primarily 17 alpha-trenbolone and trendione, and excreted in manure from implanted cattle. To predict the persistence of synthetic androgens once land-applied, aerobic degradation rates in two contrasting agricultural soil types (clay loam and a sandy soil) of both trenbolone isomers (17 alpha and 17 beta) and their primary metabolite trendione were measured and isomer interconversion was assessed. The impact of manure application was also evaluated in the clay loam soil. A pseudo first-order exponential decay model was derived assuming irreversible transformation and no impact of sorption on availability for degradation. The model generally resulted in good fits to the data. Both isomers degraded to trendione in a similar manner with half-lives (t(1/2)) on the order of a few hours to 0.5 days at applied concentrations of <= 1 mg/kg. Similar degradation rates were observed in the presence and absence of manure applied at rates typical for land-application of cattle manure. Trenbolone degradation was concentration-dependent with degradation rates decreasing with increasing applied concentrations. Trendione, whether applied directly or produced from trenbolone, persisted longer than trenbolone with t(1/2) values of I to 4 days. A small amount (1.5%) of conversion of trendione back to 17 beta-trenbolone was observed during aerobic incubation regardless of the applied concentration. A small amount of 17 alpha-isomer also converted back to 17 beta-trenbolone, presumably through trendione. In automated soils, no degradation of 17 alpha- or 17 beta-trenbolone was observed during the first 3 days, and trendione degradation was relatively small compared to a microbially active soil.
• Synthesis and SAR study of novel pseudo-steroids as potent and selective progesterone receptor antagonists
  作者：Nareshkumar Jain、George Allan、Olivia Linton、Pamela Tannenbaum、Xin Chen、Jun Xu、Peifang Zhu、Joseph Gunnet、Keith Demarest、Scott Lundeen、William Murray、Zhihua Sui

  DOI：10.1016/j.bmcl.2009.01.095

  日期：2009.7

  Synthesis of novel 7-pseudo-steroids 1c has been achieved from trenbolone 3 via an efficient 14 step sequence with overall yields of 10-15%. Various substitutions were incorporated at both the aromatic side chain as well as the D ring. The orientation of aromatic side chain at C10 plays a crucial role for progesterone receptor (PR) activity. Compound 2a (T47D = 1 nM) with -NMe2 para to the aromatic group along with spirofurane groups in the D ring was the optimal substitution. All compounds were also evaluated for glucocorticoid receptor (GR) antagonist activities in vivo in a rat and found efficacious in uterine complement C3 assay via the oral route of administrations. (C) 2009 Elsevier Ltd. All rights reserved.