3β-(t-butyl)dimethyl-siloxy-androst-5-ene-17β-carboxaldehyde | 156894-79-0

• 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: 3β-(t-butyl)dimethyl-siloxy-androst-5-ene-17β-carboxaldehyde
• 英文别名: (3S,8S,9S,10R,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carbaldehyde
• CAS: 156894-79-0
• 化学式: C₂₆H₄₄O₂Si
• 分子量: 416.72
• InChiKey: NOFDCHDBCRDMNC-YZZOFKFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.15
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3β-(t-butyl)dimethyl-siloxy-androst-5-ene-17β-carboxaldehyde 在 palladium on barium sulfate 喹啉 、 正丁基锂 、 L-酒石酸二丁酯 、 氢气 、 diethylzinc 、 二异丁基氢化铝 、 三苯基膦 、 锌 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Complexation of Vinylcyclopropanes with Zirconocene−1-butene Complex:  Application to the Stereocontrolled Synthesis of Steroidal Side Chains

  摘要：

  Reactions of vinylcyclopropane derivatives with a zirconocene-1-butene complex (''Cp2Zr'') caused regioselective cleavage of the cyclopropyl bond to give eta(3) pi-allylic and/or eta(1) sigma-allylic complexes. The regioselectivity of the bond cleavage and the formation of a eta(3) pi-allylic or eta(1) sigma-allylic complex depend on the bulkiness of the substituents on the cyclopropyl group and the presence of leaving functionality. A catalytic use of ''Cp2Zr'' in the presence of excess Grignard reagent also caused a ring opening of the vinylcyclopropane derivatives with the same sense of regiochemical selectivity. The reaction of the thermally equilibrated ''Cp2Zr''-propenylcyclopropane complex with acetone indicated the possibility for the synthesis of the steroidal side chain in either natural or unnatural forms. The synthetic utility of the present ''Cp2Zr''-vinylcyclopropane chemistry was ascertained by the stereocontrolled preparation of the C-20, C-24 dimethylated steroidal side chain which is identical to the active metabolite of vitamin D-2.

  DOI：

  10.1021/jo962064r
• 作为产物：
  描述：

  3β-t-butyldimethylsilyloxy-nor-21-pregn-5-en-20-ol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以91%的产率得到3β-(t-butyl)dimethyl-siloxy-androst-5-ene-17β-carboxaldehyde
  参考文献：
  名称：

  Acetylenic Inhibitors of C-22 Hydroxylase of Ecdysone Biosynthesis

  摘要：

  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.

  DOI：

  10.1006/bioo.1994.1003