6-(tert-butyldiphenylsilanyloxy)hex-3-en-1-ol | 927670-17-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 6-(tert-butyldiphenylsilanyloxy)hex-3-en-1-ol
• 英文别名: (E)-6-((tert-butyldiphenylsilyl)oxy)hex-3-en-1-ol；(E)-6-[tert-butyl(diphenyl)silyl]oxyhex-3-en-1-ol
• CAS: 927670-17-5
• 化学式: C₂₂H₃₀O₂Si
• 分子量: 354.565
• InChiKey: CLLGVGPNLBICSY-SNAWJCMRSA-N

物化性质

• 沸点：
  434.9±45.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  6-(tert-butyldiphenylsilanyloxy)hex-3-en-1-ol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 乙醚 、 乙腈 为溶剂， 以97%的产率得到tert-butyl(6-iodohex-3-enyloxy)diphenylsilane
  参考文献：
  名称：

  Preparation of 3-alkylpyridines. Formal total synthesis of Haliclamines A and B

  摘要：

  The formal total synthesis of two sponge alkaloids Haliclamines A and B is achieved through the preparation of 3-alkylpyridines 3, 4 and 5 via an advanced common intermediate 6. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02120-6
• 作为产物：
  描述：

  反-3-己烯二酸二甲酯 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 22.0h， 生成 6-(tert-butyldiphenylsilanyloxy)hex-3-en-1-ol
  参考文献：
  名称：

  A Biosynthetically-Inspired Synthesis of the Tetrahydrofuran Core of Obtusallenes II and IV

  摘要：

  Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set.

  DOI：

  10.1021/ol062818g

文献信息

• WO2008/21213
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and biological evaluation of new cytotoxic indazolo[4,3-gh]isoquinolinone derivatives
  作者：Manochehr Shahabi、Eva Schirmer、Karem Shanab、Theerachart Leepasert、Jana Ruzicka、Wolfgang Holzer、Helmut Spreitzer、Babette Aicher、Peter Schmidt、Lars Blumenstein、Gilbert Müller、Eckhard Günther

  DOI：10.1016/j.bmcl.2013.01.022

  日期：2013.3

  A series of indazolo[4,3-gh]isoquinolinones derivatives have been synthesized to decrease cardiotoxic side effects in comparison to Mitoxantrone. The antiproliferative effects of different side chains were investigated and tested on at least four different cell lines of cervix, ovarian, CNS, NSCLC (non-small-cell lung cancer) and colon carcinoma. In addition to antiproliferative activities, influence on cell cycle and intercalation behavior have been tested. (C) 2013 Elsevier Ltd. All rights reserved.
• Preparation of 3-alkylpyridines. Formal total synthesis of Haliclamines A and B
  作者：Jack E Baldwin、Delyth A James、Victor Lee

  DOI：10.1016/s0040-4039(99)02120-6

  日期：2000.1

  The formal total synthesis of two sponge alkaloids Haliclamines A and B is achieved through the preparation of 3-alkylpyridines 3, 4 and 5 via an advanced common intermediate 6. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of pochoxime prodrugs as potent HSP90 inhibitors
  作者：Cuihua Wang、Sofia Barluenga、Girish K. Koripelly、Jean-Gonzague Fontaine、Ruihong Chen、Jin-Chen Yu、Xiaodong Shen、John C. Chabala、James V. Heck、Allan Rubenstein、Nicolas Winssinger

  DOI：10.1016/j.bmcl.2009.04.030

  日期：2009.7

  Pochoximes are potent inhibitors of heat shock protein 90 (HSP90) based on the radicicol pharmacophores. Herein we present a pharmacokinetics and pharmacodynamics evaluation of this compound series as well as a phosphate prodrug strategy to facilitate formulation and improve oral bioavailability. (C) 2009 Elsevier Ltd. All rights reserved.
• A Biosynthetically-Inspired Synthesis of the Tetrahydrofuran Core of Obtusallenes II and IV
  作者：D. Christopher Braddock、Roshni Bhuva、David S. Millan、Yolanda Pérez-Fuertes、Craig A. Roberts、Richard N. Sheppard、Savade Solanki、Elaine S. E. Stokes、Andrew J. P. White

  DOI：10.1021/ol062818g

  日期：2007.2.1

  Sharpless asymmetric dihydroxylation was regioselective for the trans olefin in an E vs Z vs terminal triene substrate. To test a biosynthetic hypothesis, the resulting diol underwent diastereoselective bromoetherification to provide the des-chloro core of marine natural products obtusallenes II and IV. Alternatively, anionic chloride ring-opening of a Z-beta,gamma-unsaturated epoxide gave separable regioisomeric halohydrins. Bromoetherification gave the fully elaborated core of obtusallenes II and IV with all of the relative stereochemistry correctly set.