17α-ethynylandrost-4,6-dien-17β-ol-3-one | 2668-77-1

• 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: 17α-ethynylandrost-4,6-dien-17β-ol-3-one
• 英文别名: 17α-ethynylandrosta-4,6-dien-17β-ol-3-one；6-Dehydro-17α-aethinyl-testosteron；17-hydroxy-17βH-pregna-4,6-dien-20-yn-3-one；17-Hydroxy-17βH-pregna-4,6-dien-20-in-3-on；17α-ethynyl-17β-hydroxy-4,6-androstadien-3-one；(8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 2668-77-1
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: WURSFVLFUANRBL-CEGNMAFCSA-N

物化性质

• 熔点：
  260-262 °C(Solv: methanol (67-56-1); chloroform (67-66-3))
• 沸点：
  462.5±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17α-ethynylandrost-4,6-dien-17β-ol-3-one 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (3S,8R,9S,10R,13S,14S,17R)-17-Ethynyl-10,13-dimethyl-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  某些甾体3-BET-羟基-4,6-二烯的酯及其生物活性。

  摘要：

  DOI：

  10.1021/jm00339a027
• 作为产物：
  描述：

  炔孕酮 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 17α-ethynylandrost-4,6-dien-17β-ol-3-one
  参考文献：
  名称：

  Steroids. CXXXIV.¹ Derivatives of 17α-Ethylnyltestosterone and 17α-Ethynyl-19-nortestosterone

  摘要：

  DOI：

  10.1021/ja01490a049

文献信息

• Process for the preparation of pregnane derivatives
  申请人：Schering Aktiengesellschaft

  公开号：US04102908A1

  公开（公告）日：1978-07-25

  A process for the preparation of pregnane derivatives of the formula ##STR1## wherein R.sub.1 is methyl or ethyl and R.sub.2 is methyl, ethyl, formyl, or acetyl, comprises reacting a nitrate ester of the formula ##STR2## wherein R.sub.1 is as above, in the presence of a catalytic amount of a mercury salt of a lower carboxylic acid with formic acid or acetic acid in a dipolar aprotic or basic solvent or with methanol or ethanol in an aprotonic, especially water-miscible, solvent in the presence of a mineral acid.

  一种制备式的孕烷衍生物的方法##STR1##其中R.sub.1为甲基或乙基，R.sub.2为甲基、乙基、甲酰基或乙酰基，包括在存在下述式的硝酸酯的情况下反应##STR2##其中R.sub.1如上所述，在低级羧酸的汞盐的催化下与甲酸或乙酸在极性非质子或碱性溶剂中，或在无质子，特别是亲水性的溶剂中与甲醇或乙醇在矿酸的存在下反应。
• Antiprogestational agents. The synthesis of 7-alkyl steroidal ketones with anti-implantational and antidecidual activity
  作者：Joyce F. Grunwell、Harvey D. Benson、J.O'Neal Johnston、Vladimir Petrow

  DOI：10.1016/0039-128x(76)90136-7

  日期：1976.6

  A series of 7alpha- and 7beta- alkyl derivatives of steroidal 4-en- and 5-en-3-ones were prepared by 1,6-conjugate addition of organocopper reagents to various steroidal 4,6-dien-3-ones of the androstane, estrane and gonane series. Biological study of these and related compounds revealed that 17beta-hydroxy-7alpha-methyl-5-androsten-3-one (2), 17beta-hydroxy-7alpha-methyl-5-estren-3-one acetate and 17beta-hydroxy-7alpha-methyl-4-estren-3-one acetate had significant anti-implantational and antidecidual activities. The contragestative effects were associated with the latter anti-hormonal properties, and not with the androgenicity of these compounds.
• DE1010963
  申请人：——

  公开号：——

  公开（公告）日：——
• Preparation of 17α-iodoethynylandrosta- and 17α-(2-iodoethenyl) androsta-4,6-dien-17β-ol-3-ones as active site-directed photoaffinity ligands for androgen-binding proteins
  作者：Pablo J. Diaz Cruz、N.Scott Mason、Benjamin J. Danzo、Howard E. Smith

  DOI：10.1016/0039-128x(92)90027-7

  日期：1992.11

  Unsaturated analogues of androst-4-en-17 beta-ol-3-one, each with a 17 alpha-iodoethynyl or 17 alpha-(2-iodoethenyl) substituent, were prepared, and their relative binding affinities (RBAs) for androgen-binding protein (ABP) were compared with those of 5 alpha-androstan-17 beta-ol-3-one, androst-4-en-17 beta-ol-3-one, androsta-4,6-dien-17 beta-ol-3-one, and androsta-1,4,6-trien-17 beta-ol-3-one. These binding studies indicate that the iodine[125I] analogues of 17 alpha-iodoethynyl and 17 alpha-[(E)-2-iodoethenyl] derivatives of androsta-4,6-dien-17 beta-ol-3-one and androsta-1,4,6-trien-17 beta-ol-3-one will have RBAs at least twice as great as that of 5 alpha-androstan-17 beta-ol-3-one. They can be prepared from 17 alpha-ethynylandrosta-4-en-17 beta-ol-3-one, the final synthetic step using N-[125I]iodosuccinimide, and are potential radioiodinated, active site-directed photoaffinity ligands for ABP and testosterone-binding globulin.
• US4102908A
  申请人：——

  公开号：US4102908A

  公开（公告）日：1978-07-25