(8R,9S,13S,14S,16R,17S)-16-allyl-3-((tert-butyldimethylsilyl)oxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate | 234765-85-6

• 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: (8R,9S,13S,14S,16R,17S)-16-allyl-3-((tert-butyldimethylsilyl)oxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate
• 英文别名: [(8R,9S,13S,14S,16R,17S)-3-[tert-butyl(dimethyl)silyl]oxy-13-methyl-16-prop-2-enyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 234765-85-6
• 化学式: C₂₉H₄₄O₃Si
• 分子量: 468.752
• InChiKey: RPPXDOOYVXMDTP-QSDNOHAXSA-N

物化性质

• 沸点：
  500.423±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.039±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.66
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S,16R,17S)-16-allyl-3-((tert-butyldimethylsilyl)oxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate 在 sodium periodate 、 四氧化锇 、 N-甲基吲哚酮 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and evaluation of geldanamycin-estradiol hybrids

  摘要：

  Geldanamycin (GDM) binds to the Hsp90 chaperone protein and causes the degradation of several important signalling proteins. A series of novel estradiol-geldanamycin hybrids has been synthesized and evaluated for their ability to induce the selective degradation of the estrogen receptor (ER). The hybrid compounds are active and more selective than the parent causing degradation of ER and HER2, but not other GDM targets. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00185-7
• 作为产物：
  描述：

  3-(O-tert-butyl(dimethyl)silyl)estrone 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (8R,9S,13S,14S,16R,17S)-16-allyl-3-((tert-butyldimethylsilyl)oxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate
  参考文献：
  名称：

  Synthesis and evaluation of geldanamycin-estradiol hybrids

  摘要：

  Geldanamycin (GDM) binds to the Hsp90 chaperone protein and causes the degradation of several important signalling proteins. A series of novel estradiol-geldanamycin hybrids has been synthesized and evaluated for their ability to induce the selective degradation of the estrogen receptor (ER). The hybrid compounds are active and more selective than the parent causing degradation of ER and HER2, but not other GDM targets. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00185-7

文献信息

• Aerobic Linear Allylic C–H Amination: Overcoming Benzoquinone Inhibition
  作者：Christopher C. Pattillo、Iulia I. Strambeanu、Pilar Calleja、Nicolaas A. Vermeulen、Tomokazu Mizuno、M. Christina White

  DOI：10.1021/jacs.5b11294

  日期：2016.2.3

  linear allylic C-H amination reaction is reported under palladium(II)/bis-sulfoxide/Brønsted base catalysis. The reaction operates under preparative, operationally simple conditions (1 equiv of olefin, 1 atm O2 or air) with reduced Pd(II)/bis-sulfoxide catalyst loadings while providing higher turnovers and product yields than systems employing stoichiometric benzoquinone (BQ) as the terminal oxidant

  据报道，在钯(II)/双亚砜/布朗斯台德碱催化下，发生了有效的需氧线性烯丙基 CH 胺化反应。该反应在制备、操作简单的条件（1 当量烯烃、1 atm O2 或空气）下进行，减少了 Pd(II)/双亚砜催化剂的负载量，同时比采用化学计量苯醌 (BQ) 作为催化剂的系统提供更高的周转率和产品收率。终端氧化剂。Pd(II)/BQ π-酸性相互作用已在各种催化过程中被调用，并且通常被认为有利于促进还原官能化。然而，当不需要这种用于功能化的亲电激活时，高浓度的 BQ 可能会与关键配体（双亚砜）的结合竞争并抑制催化。动力学研究揭示了反应速率与 BQ 浓度之间的反比关系，表明 BQ 充当 Pd(II) 的配体，从而对催化产生抑制作用。
• A Catalytic, Brønsted Base Strategy for Intermolecular Allylic C−H Amination
  作者：Sean A. Reed、Anthony R. Mazzotti、M. Christina White

  DOI：10.1021/ja903939k

  日期：2009.8.26

  A Bronsted base activation mode for oxidative, Pd(II)/sulfoxide-catalyzed, intermolecular C-H allylic amination is reported. N,N-diisopropylethylamine was found to promote amination of unactivated terminal olefins, forming the corresponding linear allylic amine products with high levels of stereo-, regio-, and chemoselectivity. The predictable and high selectivity of this C-H oxidation method enables late-stage incorporation of nitrogen into advanced synthetic intermediates and natural products.