21,24-dinor-3β,17β-dihydroxy-chol-5-en-22-yne | 156894-83-6

• 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: 21,24-dinor-3β,17β-dihydroxy-chol-5-en-22-yne
• 英文别名: 21,24-dinor-17βH-chol-5-en-22-yne-3β,17-diol；21,24-Dinor-17βH-chol-5-en-22-in-3β,17-diol；(3S,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-17-prop-2-ynyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 156894-83-6
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: SEBHZILGNHIZGV-YRCTWBNTSA-N

物化性质

• 熔点：
  153-155 °C
• 沸点：
  459.7±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  21,24-dinor-3β,17β-dihydroxy-chol-5-en-22-yne 在 三氟甲磺酸三甲基硅酯 、 四氯苯醌 、 戴斯-马丁氧化剂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 14.0h， 生成 螺内酯
  参考文献：
  名称：

  分子内烯类捕集法对一炔丙醇进行一锅γ-内酯化

  摘要：

  已经开发了通过炔烃去质子化/硼化/氧化顺序的一锅法丙炔醇的γ-内酯化。氧化生成的炔基硼酸酯可得到相应的乙烯酮中间体，该中间体被相邻的羟基捕获，从而提供了γ-内酯。我们优化了条件，并研究了这种有效的一锅内酯化的底物范围和合成应用。

  DOI：

  10.1021/acs.orglett.1c00840
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 氢氧化钾 、 锌 作用下， 生成 21,24-dinor-3β,17β-dihydroxy-chol-5-en-22-yne
  参考文献：
  名称：

  Greenhalgh et al., Journal of the Chemical Society, 1951, p. 1190,1192

  摘要：

  DOI：

文献信息

• Ruthenium-Catalyzed Cycloisomerization−Oxidation of Homopropargyl Alcohols. A New Access to γ-Butyrolactones
  作者：Barry M. Trost、Young H. Rhee

  DOI：10.1021/ja992013m

  日期：1999.12.1

  Vinylidenemetal species, which readily form from terminal alkynes under mild conditions, have rarely been utilized as reactive intermediates in a catalytic cycle. The conversion of homopropargyl alcohols via such intermediates to metal-complexed oxacarbenes led to the development of an "oxidant" compatible with a ruthenium complex capable of performing the cycloisomerization, that would convert them to lactones. None of the oxidants known to stoichiometrically convert isolated metallooxacarbenes to esters are effective. The unconventional "oxidants", N-hydroxyimides, proved to be capable of effecting the desired transformation, with N-hydroxysuccinimide being the "oxidant" of choice. The procedure of choice employs cyclopentadienyl (1,4-cyclooctadiene) ruthenium chloride and trifuryl phosphine as the precatalyst in the presence of tetra-n-butylammonium bromide or hexafluorophosphate with N-hydroxysuccinimide as the oxidant in DMF-water at 95 degrees. In this way, a wide diversity of homopropargyl alcohols were converted to gamma-butyrolactones with excellent chemoselectivity. Lactones synthesized include an intermediate toward a platelet aggregation inhibitor, a fruit flavor principle, an inhibitor of binding of phorbol esters to PKC-alpha, a tobacco constituent, a wood constituent (quercus lactone), an aldosterone antagonist (spironolactone) precursor, and an acetogenin known for pesticidal and antitumor activities (muricatacin).
• Acetylenic Inhibitors of C-22 Hydroxylase of Ecdysone Biosynthesis
  作者：A. Mauvais、A. Burger、J.P. Roussel、C. Hetru、B. Luu

  DOI：10.1006/bioo.1994.1003

  日期：1994.3

  Acetylenic derivatives of cholesterol designed to be inhibitors of ecdysteroid biosynthesis were prepared. The side chains of these compounds differ additionally from that of cholesterol by stereochemical modifications at C-17 and C-20. A bicyclic acetylenic compound containing the partial structure of the C and D rings of the cholesterol nucleus was also synthesized. These compounds were devised with the aim of inhibiting the C-22 hydroxylation of ecdysone biosynthesis by a suicide substrate mechanism. One of these molecules inhibits very efficiently the synthesis of ecdysone in prothoracic glands in vitro. (C) 1994 Academic Press, Inc.
• Steroidal Aldosterone Blockers. I
  作者：JOHN A. CELLA、EDWARD A. BROWN、ROBERT R. BURTNER

  DOI：10.1021/jo01088a004

  日期：1959.6
• Magrath et al., Journal of the Chemical Society, 1951, p. 845
  作者：Magrath et al.

  DOI：——

  日期：——