3β-(4'-methoxyphenyl)cholest-5-ene | 78406-16-3

• 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-(4'-methoxyphenyl)cholest-5-ene
• 英文别名: (3S,8S,9S,10R,13R,14S,17R)-3-(4-methoxyphenyl)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 78406-16-3
• 化学式: C₃₄H₅₂O
• 分子量: 476.786
• InChiKey: JAKDMHFIKZSEHP-VCTHZOALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  胆固醇碘化物 、 trichloro-(4-methoxyphenyl)stannane 在 2,2'-联吡啶 、 potassium tert-butylate 、 nickel dichloride 作用下， 以 异丁醇 、 叔丁醇 为溶剂， 反应 12.0h， 以56%的产率得到3β-(4'-methoxyphenyl)cholest-5-ene
  参考文献：
  名称：

  Stille Cross-Couplings of Unactivated Secondary Alkyl Halides Using Monoorganotin Reagents

  摘要：

  The first catalyst that achieves Stille cross-couplings of secondary (as well as primary) alkyl halides has been developed. The method employs easily handled and inexpensive catalyst components (NiCl2 and 2,2'-bipyridine) and, through the use of monoorganotin reagents, avoids the formation of toxic and difficult-to-remove triorganotin side products.

  DOI：

  10.1021/ja0436300

文献信息

• Highly diastereoselective Csp3–Csp2 Negishi cross-coupling with 1,2-, 1,3- and 1,4-substituted cycloalkylzinc compounds
  作者：Tobias Thaler、Benjamin Haag、Andrei Gavryushin、Katrin Schober、Evelyn Hartmann、Ruth M. Gschwind、Hendrik Zipse、Peter Mayer、Paul Knochel

  DOI：10.1038/nchem.505

  日期：2010.2

  Stereoselective functionalizations of organic molecules are of great importance to modern synthesis. A stereoselective preparation of pharmaceutically active molecules is often required to ensure the appropriate biological activity. Thereby, diastereoselective methods represent valuable tools for an efficient set-up of multiple stereocentres. In this article, highly diastereoselective Csp3 Negishi cross-couplings

  有机分子的立体选择性功能化对现代合成非常重要。通常需要药物活性分子的立体选择性制备以确保适当的生物活性。因此，非对映选择性方法代表了有效设置多个立体中心的宝贵工具。在本文中，高度非对映选择性 C sp 3报道了各种环烷基锌试剂与芳基卤化物的 Negishi 交叉偶联。在所有情况下，都获得了热力学最稳定的立体异构体。值得注意的是，这种非对映选择性偶联不仅适用于 1,2- 取代的环状系统，而且适用于 1,3- 和 1,4- 取代的环己基锌试剂。通过核磁共振实验和密度泛函理论计算研究了这种远程立体控制的起源。提出了基于这些实验和理论数据的详细机制。
• Montmorillonite Clay Catalysis. VIII. Synthesis of Arylcholestenes by Friedelcrafts Reaction Catalysed by Montmorillonite K-10.
  作者：Li-Jun Li、Bo Lu∗∗、Tong-Shuang Li、Ji-Tai Li

  DOI：10.1080/00397919808006843

  日期：1998.4

  A series of 3 beta-arylcholestenes were synthesised by Friedel-Crafts reaction of cholesterol with arenes catalysed by montmorillonite K-10.
• Stille Cross-Couplings of Unactivated Secondary Alkyl Halides Using Monoorganotin Reagents
  作者：David A. Powell、Toshihide Maki、Gregory C. Fu

  DOI：10.1021/ja0436300

  日期：2005.1.1

  The first catalyst that achieves Stille cross-couplings of secondary (as well as primary) alkyl halides has been developed. The method employs easily handled and inexpensive catalyst components (NiCl2 and 2,2'-bipyridine) and, through the use of monoorganotin reagents, avoids the formation of toxic and difficult-to-remove triorganotin side products.