(17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 3-(methyl ester) | 94887-68-0

• 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: (17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 3-(methyl ester)
• 英文别名: (8R,9S,13S,14S,17R)-3-methoxy-13-methyl-17-((E)-2-(tributylstannyl)vinyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol；3-methoxy-17α-(E-2-tributylstannylvinyl)-1,3,5(10)-estratrien-17β-ol；(8R,9S,13S,14S,17R)-3-methoxy-13-methyl-17-[(Z)-2-tributylstannylethenyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol
• CAS: 94887-68-0
• 化学式: C₃₃H₅₄O₂Sn
• 分子量: 601.501
• InChiKey: QYAMNRYKRHNPLA-DNRVBMAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.23
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  (17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 3-(methyl ester) 生成 (17α,20Z)-21-iodo-19-norpregna-1,3,5,(10),20-tetraene-3,17-diol 3-(methyl ether)
  参考文献：
  名称：

  ALI, H.;ROUSSEAU, J.;CHAFFARI, M. A.;VAN, LIER J. E., J. MED. CHEM., 31,(1988) N 10, C. 1946-1950

  摘要：

  DOI：
• 作为产物：
  描述：

  美雌醇 在 三正丁基氢锡 作用下， 生成 (17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 3-(methyl ester)
  参考文献：
  名称：

  Estrogenic 17.alpha.-halogen-vinylestranes

  摘要：

  17.alpha.-溴-.alpha.和17.alpha.-碘-乙烯基-雌甾烷衍生物的一般化学式I如下：其中X是Z或E位置的溴或碘原子，R.sup.1是氢、羟基或酰氧基，碳原子数最多为3，R.sup.2是氢、碳原子数最多为3的烷基以及碳原子数最多为7的烷酰基和芳酰基，R.sup.3是氢或甲基，R.sup.4是.alpha.或.beta.位置的氢原子，R.sup.5是氢、甲基或甲氧基，R.sup.6是氢或甲基，具有药理学作用，其作用特点类似于乙炔雌二醇，并且以其放射性标记化合物的形式也是有价值的诊断介质。Z-异构体可以通过一种新的方法制备，即将相应的17.alpha.-乙炔类固醇与三烷基（或苯基）锡氢化合物反应，并加入自由基前体。

  公开号：

  US04725426A1

文献信息

• Heterobimetallic Control of Regioselectivity in Alkyne Hydrostannylation: Divergent Syntheses of α- and (<i>E</i>)<i>-</i>β<i>-</i>Vinylstannanes via Cooperative Sn–H Bond Activation
  作者：Li-Jie Cheng、Neal P. Mankad

  DOI：10.1021/jacs.9b00068

  日期：2019.2.27

  terminal alkynes under mild conditions, with Markovnikov/anti-Markovnikov selectivity controlled by the Cu/M pairing. By using the MeIMesCu-FeCp(CO)2 catalyst, a variety of α-vinylstannanes were produced from simple alkyl-substituted alkynes and Bu3SnH in high yield and good regioselectivity; these products are challenging to access under mononuclear metal-catalyzed hydrostannylation conditions. In addition

  通过可调异双金属 (NHC)Cu-[MCO] 催化剂（[MCO] = FeCp(CO)2 或 Mn(CO)5）协同 Sn-H 键活化氢锡烷 (Bu3SnH) 能够在温和条件下催化氢化锡烷基化末端炔, 马尔科夫尼科夫/反马尔科夫尼科夫选择性由铜/M 配对控制。通过使用MeIMesCu-FeCp(CO)2催化剂，以简单的烷基取代炔烃和Bu3SnH为原料，以高产率和良好的区域选择性制备了多种α-乙烯基锡烷；这些产品在单核金属催化氢化锡烷基化条件下难以获得。此外，在 Cu/Fe 催化条件下，芳基取代的炔烃观察到反向区域选择性，得到 (E)-β-乙烯基锡烷作为主要产物。另一方面，通过使用 IMesCu-Mn(CO)5 催化剂，由伯、仲和叔烷基取代的炔烃制备了多种 (E)-β-乙烯基锡烷，因此证明了由 Cu/Fe 与 Cu/Mn 配对控制的炔烃氢化锡烷基化的不同区域选择性。这两种方法都适用于克级乙烯基
• Illuminating Stannylation
  作者：Kyoka Sakamoto、Yuki Nagashima、Chao Wang、Kazunori Miyamoto、Ken Tanaka、Masanobu Uchiyama

  DOI：10.1021/jacs.1c00887

  日期：2021.4.21
• Synthesis, receptor binding, and tissue distribution of (17.alpha.,20E)- and (17.alpha.,20Z)-21-[125I]Iodo-19-norpregna-1,3,5-(10),20-tetraene-3,17-diol
  作者：H. Ali、J. Rousseau、M. A. Ghaffari、J. E. Van Lier

  DOI：10.1021/jm00118a013

  日期：1988.10

  The isomeric (17 alpha,20E)- and (17 alpha,20Z)-(iodovinyl)estradiol derivatives 3 and 6, and their no-carrier-added (nca) [125I]iodovinyl analogues, were tested for their relative target tissue retention and binding affinity for the estrogen receptor. The (iodovinyl)estradiols 3 and 6 were prepared via destannylation of the (17 alpha,20E)- and (17 alpha,20Z)-tributylstannyl precursors 2 and 4 with retention of configuration. Selective formation of the E or Z isomers 2 and 4 during the reaction of 17 alpha-ethynylestradiol 1a with tri-n-butyltin hydride was controlled by the presence or absence of the catalyst, the polarity of the solvent, and the reaction temperature. The nca [125I]iodovinyl analogues [125I]-3a and [125I]-6a were obtained in good radiochemical yield and high purity by treatment of 2a and 4a with [125I]NaI in the presence of H2O2 and chloroamine-T, respectively. Of the two isomeric iodovinyl derivatives 3 and 6, the 20Z isomer 6a exhibited the highest receptor binding affinity and the [125I]-6a gave the highest in vivo receptor-mediated target tissue uptake.