3,20-dioxo-4-pregnene-16α-carbonotrile | 1424-05-1

• 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: 3,20-dioxo-4-pregnene-16α-carbonotrile
• 英文别名: 16α-cyanoprogesterone；3,20-dioxo-pregn-4-ene-16α-carbonitrile；3,20-Dioxo-pregn-4-en-16α-carbonitril；16α-Cyan-4-pregnen-3.20-dion；16α-Cyano-progesteron；(8S,9S,10R,13S,14S,16R,17S)-17-acetyl-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-16-carbonitrile
• CAS: 1424-05-1
• 化学式: C₂₂H₂₉NO₂
• 分子量: 339.478
• InChiKey: DONRZHSJKBXCBF-POJZBZBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  57.93
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,20-dioxo-4-pregnene-16α-carbonotrile 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 作用下， 以 甲醇 为溶剂， 反应 19.08h， 生成 16α-dimethylaminomethyl-3β-pyrrolidino-5-pregnene-20ξ-yl-acetate
  参考文献：
  名称：

  Steroids and related studies: part 90 — certain new azasteroidal bisquaternary neuromuscular blockers

  摘要：

  Bisquaternary azasteroids HS-1177 7 and HS-1181 8, structurally resembling chandonium 2 in rings A and B characteristics, and HS-1184 6, in part resembling HS-467 1 have been prepared and characterised. All 3 compounds, each possessing 16alpha-methyltrimethylammonium functions, were prepared as potential neuromuscular blocking agents. They were found to be active but less effective than chandonium.

  DOI：

  10.1016/0223-5234(93)90138-5
• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 甲醇 、 环己酮 、 aluminum isopropoxide 作用下， 生成 3,20-dioxo-4-pregnene-16α-carbonotrile
  参考文献：
  名称：

  16取代类固醇

  摘要：

  描述了3β-乙酰氧基-5,16-孕烷-20-与氰化物离子和某些活性亚甲基化合物的反应。显示了初始产物的后续转化以产生各种16-取代的孕烯醇酮和孕酮。

  DOI：

  10.1016/0040-4020(59)80060-0

文献信息

• Modified steroid hormones-XXXIII
  作者：D. Burn、G. Cooley、M.T. Davies、J.W. Ducker、B. Ellis、P. Feather、A.K. Hiscock、D.N. Kirk、A.P. Leftwick、V. Petrow、D.M. Williamson

  DOI：10.1016/s0040-4020(01)98622-3

  日期：1964.1

  Reaction between steroidal 3-alkoxy-3,5-dienes and the Vilsmeier reagent leads to high yields of the corresponding 6-formyl derivatives. These intermediates are reduced to 3-alkoxy-6-hydroxymethyl-3,5-dienes which undergo dehydration with acids to 6-methylene-4-en-3-ones.

  甾族3-烷氧基-3，5-二烯与Vilsmeier试剂之间的反应导致相应的6-甲酰基衍生物的高产率。这些中间体被还原成3-烷氧基-6-羟甲基-3，5-二烯，其经酸脱水成6-亚甲基-4-en-3-one。
• Synthesis and stereochemistry of 16-substituted pregnenes and isopregnenes
  作者：P. Crabbé、L.M. Guerrero、J. Romo、F. Sánchez-Viesca

  DOI：10.1016/0040-4020(63)80003-4

  日期：1963.1

  The synthesis, stereochemistry and configuration stability of 16α- and 16β-carboyx-Δ5-pregnene and 16α- and 16β-carboxy-17α-(iso)-Δ5-pregnene-stereoisomers were investigated.

  16α-和16β-carboyx-Δ的合成，立体化学和构型稳定性5 -pregnene和16α-和16β羧基- 17α-（异）-Δ 5 -pregnene立体异构体进行了研究。
• The addition of hydrocyanic acid to Δ16-pregnen-20-ones
  作者：J. Romo

  DOI：10.1016/s0040-4020(01)82608-9

  日期：1958.1

  Hydrocyanic acid adds to the 16-double bond of Δ5,16-pregnadien-3β-ol-20-one acetate to produce 16α-cyano-Δ5-pregnen-3β-ol-20-one. Similar additions of hydrocyanic acid to Δ16-20-oxo pregnenes are described. By alkaline hydrolysis of the 16α-nitrile group the corresponding acid was obtained, of which several derivatives are described.

  氢氰酸增加Δ的16双键-5,16- -pregnadien-3β醇-20-酮乙酸盐以产生16α氰基Δ 5 -pregnen-3β醇-20-酮。类似的增加氢氰酸到Δ 16 -20氧代pregnenes中描述。通过16α-腈基的碱水解，得到相应的酸，其中描述了几种衍生物。
• Abraham; Jindal; Singh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 10, p. 799 - 801
  作者：Abraham、Jindal、Singh

  DOI：——

  日期：——
• Abraham; Jindal; Singh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 12, p. 1051 - 1052
  作者：Abraham、Jindal、Singh

  DOI：——

  日期：——