estradiol-17β 3-propargyl ether | 28151-61-3

• 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: estradiol-17β 3-propargyl ether
• 英文别名: 3-O-propargyl estradiol；(8R,9S,13S,14S,17S)-13-methyl-3-prop-2-ynoxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-ol
• CAS: 28151-61-3
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: FKSIYLRRFQFAKK-MJCUULBUSA-N

物化性质

• 熔点：
  108.5-110.5 °C
• 沸点：
  467.3±45.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  estradiol-17β 3-propargyl ether 在 benzyltriethylammonium tetrathiomolybdate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以82%的产率得到雌二醇
  参考文献：
  名称：

  使用四硫代钼酸盐选择性去保护炔丙基醚

  摘要：

  苄基三乙基四硫代钼酸铵，[PhCH2NEt3](2)MoS4, 1 以高产率选择性地对醇和酚的炔丙基醚进行脱保护。硝基、醛、酮和烯丙基等易还原基团不受影响。

  DOI：

  10.1055/s-1997-6132
• 作为产物：
  描述：

  3-O-propagylestrone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到estradiol-17β 3-propargyl ether
  参考文献：
  名称：

  具有“高度对称依赖性”胶凝能力的“点击”雌二醇基低分子量胶凝剂新家族。

  摘要：

  本文报道的是新颖的“点击的”基于雌二醇的LMWG家族的发现，其胶凝能力高度依赖于胶凝剂的对称性。这些LMWG在H（2）O存在下胶凝不同的有机溶剂，即使浓度低至0.04 wt％，也可以使用“点击”化学方法轻松获得。

  DOI：

  10.1039/c1cc13251b

文献信息

• Radical borylation of vinyl azides with NHC-boranes: divergent synthesis of α-boryl ketones and borylated triazoles
  作者：Yifei Zhang、Yangzhen Liao、Peijun Liu、Yu Ran、Xiaozu Liu

  DOI：10.1039/d2ob00076h

  日期：——

  A divergent radical borylation of vinyl azides with N-heterocyclic carbene (NHC) boranes in the presence of tBuSH is described. The protocol enables the divergent synthesis of α-boryl ketones and borylated triazoles with excellent functional group tolerance and a broad substrate scope. Remarkably, this work shows that vinyl azides can serve as unprecedented five-atom synthons for the construction of

  描述了在t BuSH存在下，乙烯基叠氮化物与 N-杂环卡宾 (NHC) 硼烷的发散自由基硼化反应。该协议能够实现α-硼基酮和硼化三唑的不同合成，具有优异的官能团耐受性和广泛的底物范围。值得注意的是，这项工作表明乙烯基叠氮化物可以作为前所未有的五原子合成子用于构建 1,2,3-三唑，而无需 N 2挤出。
• Boron estrogens: Synthesis, biochemical and biological testing of estrone and estradiol-17β 3-carboranylmethyl ethers
  作者：Frederick Sweet

  DOI：10.1016/s0039-128x(81)80020-7

  日期：1981.2

  Synthesis, biochemical and biological testing of the first carborane derivatives of estrogens are described. Estrone 3-carboranylmethyl ether was synthesized in two steps from estrone. Reduction of estrone 3-carboranylmethyl ether with sodium borohydride provided estradiol-17 beta 3-carboranylmethyl ether. Enzyme kinetic measurements showed that estrone 3-carboranylmethyl ether is a substrate for human placental 17 beta-hydroxysteroid dehydrogenase with Km = 5 x 10(-6)M, and Vmax = 0.016 mumol min-1 microgram -1. The relative affinity constant of estradiol-17 beta 3-carboranylmethyl ether for rat uterine estrogen receptor was 0.5 (compared with a value of 100 for estradiol-17 beta). Consistent with its low affinity for estrogen receptor, the dose-dependent uterotropic response to estradiol-17 beta 3-carboranylmethyl ether in castrated female rats was one sixtieth that of estradiol-17 beta. None of the tested rats had a toxic reaction to estradiol-17 beta 3-carboranylmethyl ether. These results demonstrate that exceptionally stable carborane derivatives of estrogens can be synthesized with preservation of their biochemical and biological properties. Boron-containing estrogens may be useful for thermal neutron capture therapy of cancers with estrogen receptors to concentrate boron in the cell nucleus.
• Selective Deprotection of Propargyl Ethers Using Tetrathiomolybdate
  作者：V. Swamy、Palanichamy Ilankumaran、Srinivasan Chandrasekaran

  DOI：10.1055/s-1997-6132

  日期：1997.6

  Benzyltriethylammonium tetrathiomolybdate, [PhCH2NEt3](2)MoS4, 1 deprotects propargyl ethers of alcohols and phenols in a selective manner in high yields. Easily reducible groups like nitro, aldehyde, keto and allyl are not affected.

  苄基三乙基四硫代钼酸铵，[PhCH2NEt3](2)MoS4, 1 以高产率选择性地对醇和酚的炔丙基醚进行脱保护。硝基、醛、酮和烯丙基等易还原基团不受影响。
• A new family of “clicked” estradiol-based low-molecular-weight gelators having highly symmetry-dependent gelation ability
  作者：Pedro Ramírez-López、María C. de la Torre、María Asenjo、Julio Ramírez-Castellanos、José M. González-Calbet、Alejandra Rodríguez-Gimeno、Carmen Ramírez de Arellano、Miguel A. Sierra

  DOI：10.1039/c1cc13251b

  日期：——

  Reported herein is the discovery of a novel family of "clicked" estradiol-based LMWGs whose gelation ability highly depends on the gelator symmetry. These LMWGs that gel different organic solvents in the presence of H(2)O even at concentrations as low as 0.04 wt% are readily accessible using "click" chemistry.

  本文报道的是新颖的“点击的”基于雌二醇的LMWG家族的发现，其胶凝能力高度依赖于胶凝剂的对称性。这些LMWG在H（2）O存在下胶凝不同的有机溶剂，即使浓度低至0.04 wt％，也可以使用“点击”化学方法轻松获得。