estrone ethylene ketal 3-(N,N-diethyl)carbamate | 141807-42-3

• 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: estrone ethylene ketal 3-(N,N-diethyl)carbamate
• 英文别名: [(8'R,9'S,13'S,14'S)-13'-methylspiro[1,3-dioxolane-2,17'-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene]-3'-yl] N,N-diethylcarbamate
• CAS: 141807-42-3
• 化学式: C₂₅H₃₅NO₄
• 分子量: 413.557
• InChiKey: JJEQQZCGNBGHGV-SVPADUAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  estrone ethylene ketal 3-(N,N-diethyl)carbamate 在 盐酸 、 lithium aluminium tetrahydride 、 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 水 为溶剂， 反应 31.5h， 生成 雌酚酮
  参考文献：
  名称：

  Synthetic Approaches towards 4-Functionalized Estrone Derivatives

  摘要：

  Directed ortho-lithiation of estrone carbamate followed by reaction with electrophiles afforded 2-substituted estrone derivatives. Reductive cleavage of the carbamate group followed by O-allylation and Claisen rearrangement led to new 4-functionalized estrone derivatives.

  DOI：

  10.1055/s-0032-1316816
• 作为产物：
  描述：

  雌酚酮 在 三乙胺 、 原甲酸三甲酯 作用下， 以 吡啶 、 甲苯 、 乙腈 为溶剂， 生成 estrone ethylene ketal 3-(N,N-diethyl)carbamate
  参考文献：
  名称：

  Synthetic Approaches towards 4-Functionalized Estrone Derivatives

  摘要：

  Directed ortho-lithiation of estrone carbamate followed by reaction with electrophiles afforded 2-substituted estrone derivatives. Reductive cleavage of the carbamate group followed by O-allylation and Claisen rearrangement led to new 4-functionalized estrone derivatives.

  DOI：

  10.1055/s-0032-1316816

文献信息

• Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp²–B Bonds via C–O Bond Activation
  作者：Shasha Geng、Juan Zhang、Shuo Chen、Zhengli Liu、Xiaoqin Zeng、Yun He、Zhang Feng

  DOI：10.1021/acs.orglett.0c01937

  日期：2020.7.17

  Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C–O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities

  在本文中，我们描述了通过C-O键的活化，铁催化的烯基和芳基氨基甲酸酯的硼酸酯化反应。该方案显示出高效率，广泛的底物范围以及生物相关化合物的后期硼化，因此在药物化学中提供了潜在的应用。而且，该方法能够使酚衍生物进行正交转化，并且还为合成多取代的芳烃提供了良好的机会。初步的机理研究表明，通过自由基途径的Fe II / Fe III催化循环可能与反应有关。
• C–O Bond Silylation Catalyzed by Iron: A General Method for the Construction of Csp²–Si Bonds
  作者：Juan Zhang、Yun Zhang、Shasha Geng、Shuo Chen、Zhengli Liu、Xiaoqin Zeng、Yun He、Zhang Feng

  DOI：10.1021/acs.orglett.0c00633

  日期：2020.4.3

  The iron-catalyzed construction of Csp2–Si bonds via unreactive C–O bonds possesses a challenging topic in organic chemistry. Herein we report an iron-catalyzed silylation of aryl and alkenyl carbamates via C–O bond activation. This protocol features high efficiency and a broad substrate scope, enabling the late-stage silylation of biorelevant compounds and thus providing a good method to access valuable

  通过非反应性C-O键的铁催化Csp 2 -Si键结构在有机化学中具有挑战性。在这里，我们报告通过C–O键激活的铁催化的芳基和烯基氨基甲酸酯的甲硅烷基化反应。该方案具有高效和广泛的底物范围的特​​点，可实现生物相关化合物的后期甲硅烷基化，从而提供了一种访问药物化学中有价值的基序的好方法。此外，该方案能够使酚衍生物进行正交转化，并且还允许通过氨基甲酸酯基团作为指导基团来合成多取代的芳烃。
• Cine Substitution of Arenes Using the Aryl Carbamate as a Removable Directing Group
  作者：Tehetena Mesganaw、Noah F. Fine Nathel、Neil K. Garg

  DOI：10.1021/ol301275u

  日期：2012.6.1

  An efficient and controlled means to achieve a rare cine substitution of arenes is reported. The methodology relies on the strategic use of aryl O-carbamates as readily removable directing groups for arene functionallzation. The removal of aryl carbamates is achieved by employing an airstable Ni(II) precatalyst, along with an inexpensive reducing agent, to give synthetically useful yields across a range of substrates. The net cine substitution process offers a new strategy for analogue synthesis, which complements the well-established logic for achieving arene functionalization by ipso substitution.
• Synthetic Approaches towards 4-Functionalized Estrone Derivatives
  作者：Andreas Kirschning、Uwe Schön、Josef Messinger、Wladimir Solodenko

  DOI：10.1055/s-0032-1316816

  日期：——

  Directed ortho-lithiation of estrone carbamate followed by reaction with electrophiles afforded 2-substituted estrone derivatives. Reductive cleavage of the carbamate group followed by O-allylation and Claisen rearrangement led to new 4-functionalized estrone derivatives.