3-methoxy-17,17α-dimethyl-17α-homo-18-norestra-1,3,5(10),13,15,17-hexane | 147587-76-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-methoxy-17,17α-dimethyl-17α-homo-18-norestra-1,3,5(10),13,15,17-hexane
• 英文别名: 3-methoxy-17,17a-dimethyl-17a-homo-18-norestra-1,3,5(10),13,15,17-hexaene；17,17a-dimethyl-3-methoxy-D-homogona-1,3,5(10),13,15,17(17a)-hexaene；(4bR,10bS)-8-methoxy-1,2-dimethyl-4b,5,6,10b,11,12-hexahydrochrysene
• CAS: 147587-76-6
• 化学式: C₂₁H₂₄O
• 分子量: 292.421
• InChiKey: SVPGQDDVDPIIAW-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methoxy-17,17α-dimethyl-17α-homo-18-norestra-1,3,5(10),13,15,17-hexane 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 以76%的产率得到17,17a-dimethyl-3-hydroxy-D-homogona-1,3,5(10),13,15,17(17a)-hexaene
  参考文献：
  名称：

  Synthesis and antimitotic activity of novel 2-methoxyestradiol analogs. Part III

  摘要：

  The syntheses and antimitotic activity of several novel analogs of 2-methoxyestradiol are described. Structural modifications include ring-D homologation, aromatization of the six-membered ring-D to a chrysine type molecule, and introduction of unsaturation in five-membered ring-D along with substitution of alkyl and ethynyl groups for the 17 beta-hydroxy function. of nine analogs synthesized, five have demonstrated superior antiproliferative activities compared to 2-methoxyestradiol. (C) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.10.016
• 作为产物：
  描述：

  美雌醇 以 甲苯 为溶剂， 生成 3-methoxy-17,17α-dimethyl-17α-homo-18-norestra-1,3,5(10),13,15,17-hexane
  参考文献：
  名称：

  微波辅助立体选择性杂环化合成雌酮系列中的新型环 d-稠合芳基吡唑啉

  摘要：

  雌酮系列中新型环 d-稠合 2-吡唑啉的微波辅助合成可从甾体 α,β-烯酮和肼衍生物有效地进行。16-亚苄基雌酮 3-甲基醚与肼在乙酸中的闭环反应产生了两个 16,17-顺式稠合吡唑啉的 2:1 非对映异构体混合物，这与之前关于立体选择性和产物的文献数据相反结构体。然而，美雌醇衍生的不饱和酮与不同芳基肼在酸性乙醇中的环化反应以良好至极好的收率提供杂环产物，而与所用试剂的芳环上存在的取代基无关。MW 条件还允许与对硝基苯肼发生闭环反应，这在常规加热下是不利的。

  DOI：

  10.3390/molecules24030569

文献信息

• WO2008/137599
  申请人：——

  公开号：——

  公开（公告）日：——
• Steroids 49. Investigations on the dehydration of 17α-ethynl-17β- hydroxysteroids
  作者：Irén Vincze、Magdalena L″okös、Tamás Bakos、Anna Dancsi、Marianna Mák

  DOI：10.1016/0039-128x(93)90022-f

  日期：1993.5

  The acidic dehydration of 17alpha-ethynyl-17beta-hydroxysteroids (1-3) was investigated. On reaction with thionyl chloride, phosphorus oxychloride, and formic acid, the desired dehydration was accompanied by chlorination, Wagner-Meerwein rearrangement, and D-homoaromatic rearrangement. The structure of the product from the transformation of 17beta-hydroxypregn-20-yne derivative (3) on reaction with formic acid was misjudged. It was regarded as a pregn-16-en-20-yne (10) instead of the actually rearranged D-homoaromatic compound (11). As a consequence, physical data corresponding to this latter structure have been cited in the literature as those of pregn-16-en-20-yne derivative (10). This confusion prompted us to prepare compounds of both types (4, 9, 10, and 11), the characterization of which is here described.
• Pindur, Ulf; Schall, Thomas, Liebigs Annalen der Chemie, 1993, # 10, p. 1099 - 1104
  作者：Pindur, Ulf、Schall, Thomas

  DOI：——

  日期：——
• Synthesis and antimitotic activity of novel 2-methoxyestradiol analogs. Part III
  作者：Pemmaraju N. Rao、James W. Cessac、James W. Boyd、Arthur D. Hanson、Jamshed Shah

  DOI：10.1016/j.steroids.2007.10.016

  日期：2008.2

  The syntheses and antimitotic activity of several novel analogs of 2-methoxyestradiol are described. Structural modifications include ring-D homologation, aromatization of the six-membered ring-D to a chrysine type molecule, and introduction of unsaturation in five-membered ring-D along with substitution of alkyl and ethynyl groups for the 17 beta-hydroxy function. of nine analogs synthesized, five have demonstrated superior antiproliferative activities compared to 2-methoxyestradiol. (C) 2007 Elsevier Inc. All rights reserved.
• Microwave-Assisted Stereoselective Heterocyclization to Novel Ring d-fused Arylpyrazolines in the Estrone Series
  作者：Gergő Mótyán、Barnabás Molnár、János Wölfling、Éva Frank

  DOI：10.3390/molecules24030569

  日期：——

  16-benzylidene estrone 3-methyl ether with hydrazine in acetic acid resulted in a 2:1 diastereomeric mixture of two 16,17-cis fused pyrazolines, which is contrary to the former literature data for both stereoselectivity and product structure. However, the cyclization reactions of a mestranol-derived unsaturated ketone with different arylhydrazines in acidic ethanol furnished the heterocyclic products in good

  雌酮系列中新型环 d-稠合 2-吡唑啉的微波辅助合成可从甾体 α,β-烯酮和肼衍生物有效地进行。16-亚苄基雌酮 3-甲基醚与肼在乙酸中的闭环反应产生了两个 16,17-顺式稠合吡唑啉的 2:1 非对映异构体混合物，这与之前关于立体选择性和产物的文献数据相反结构体。然而，美雌醇衍生的不饱和酮与不同芳基肼在酸性乙醇中的环化反应以良好至极好的收率提供杂环产物，而与所用试剂的芳环上存在的取代基无关。MW 条件还允许与对硝基苯肼发生闭环反应，这在常规加热下是不利的。