19-norandrosta-1,5-dien-3,17-dione | 892849-05-7

• 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: 19-norandrosta-1,5-dien-3,17-dione
• 英文别名: (8R,9S,10R,13S,14S)-13-methyl-4,7,8,9,10,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione
• CAS: 892849-05-7
• 化学式: C₁₈H₂₂O₂
• 分子量: 270.371
• InChiKey: WLANBADNNBNASE-QXUSFIETSA-N

物化性质

• 熔点：
  161-163 °C(Solv: ethyl ether (60-29-7); methanol (67-56-1))
• 沸点：
  436.5±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  19-norandrosta-1,5-dien-3,17-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.22h， 以40%的产率得到17β-hydroxy-19-norandrosta-1,5-dien-3-one
  参考文献：
  名称：

  First synthesis of a steroid containing an unstable 19-nor-androsta-1,5-dien-3-one system

  摘要：

  Mechanisms involved in the maintenance of human pregnancy and initiation of labour are poorly defined. A novel steroid hormone named estradienolone (ED), and having an unusual 19-nor-androsta- 1,5-dien-3-one system, was previously reported. However, ED is scarcely available from urine, placenta and blood of pregnant women. For this reason, we have synthesized ED in order to verify its proposed structure. Although a 1,5-dien-3-one system had already been described for a C19-steroid (androstane) nucleus (no possible aromatization), the synthesis of the 19-nor-analogue is a major challenge because this system is very sensitive to aromatization. We now describe the successful construction and characterization of this unstable system. Starting from nortestosterone, the synthesis of 17 beta-hydroxy-19-nor-androsta-1,5-dien-3-one (1) is based on a protection of the 5,6-double bond, the introduction of the second 1,2-double bond, the careful recovery of the exo double bond and a final regioselective oxidation or reduction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.063
• 作为产物：
  描述：

  诺龙 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 苯基氯化硒 、 硼烷 、 potassium tert-butylate 、 碳酸氢钠 、 potassium tri-sec-butyl-borohydride 、 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 原甲酸三乙酯 、 pyridinium chlorochromate 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 、 叔丁醇 为溶剂， 反应 124.0h， 生成 19-norandrosta-1,5-dien-3,17-dione
  参考文献：
  名称：

  First synthesis of a steroid containing an unstable 19-nor-androsta-1,5-dien-3-one system

  摘要：

  Mechanisms involved in the maintenance of human pregnancy and initiation of labour are poorly defined. A novel steroid hormone named estradienolone (ED), and having an unusual 19-nor-androsta- 1,5-dien-3-one system, was previously reported. However, ED is scarcely available from urine, placenta and blood of pregnant women. For this reason, we have synthesized ED in order to verify its proposed structure. Although a 1,5-dien-3-one system had already been described for a C19-steroid (androstane) nucleus (no possible aromatization), the synthesis of the 19-nor-analogue is a major challenge because this system is very sensitive to aromatization. We now describe the successful construction and characterization of this unstable system. Starting from nortestosterone, the synthesis of 17 beta-hydroxy-19-nor-androsta-1,5-dien-3-one (1) is based on a protection of the 5,6-double bond, the introduction of the second 1,2-double bond, the careful recovery of the exo double bond and a final regioselective oxidation or reduction. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.063

文献信息

• First synthesis of a steroid containing an unstable 19-nor-androsta-1,5-dien-3-one system
  作者：Christine Cadot、Donald Poirier、Anie Philip

  DOI：10.1016/j.tet.2006.02.063

  日期：2006.5

  Mechanisms involved in the maintenance of human pregnancy and initiation of labour are poorly defined. A novel steroid hormone named estradienolone (ED), and having an unusual 19-nor-androsta- 1,5-dien-3-one system, was previously reported. However, ED is scarcely available from urine, placenta and blood of pregnant women. For this reason, we have synthesized ED in order to verify its proposed structure. Although a 1,5-dien-3-one system had already been described for a C19-steroid (androstane) nucleus (no possible aromatization), the synthesis of the 19-nor-analogue is a major challenge because this system is very sensitive to aromatization. We now describe the successful construction and characterization of this unstable system. Starting from nortestosterone, the synthesis of 17 beta-hydroxy-19-nor-androsta-1,5-dien-3-one (1) is based on a protection of the 5,6-double bond, the introduction of the second 1,2-double bond, the careful recovery of the exo double bond and a final regioselective oxidation or reduction. (c) 2006 Elsevier Ltd. All rights reserved.