(4R)-5-(tert-butyldimethylsiloxy)-4-methylpent-1-yne | 152755-20-9

• 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: (4R)-5-(tert-butyldimethylsiloxy)-4-methylpent-1-yne
• 英文别名: (R)-(1,1-dimethylethyl)dimethyl[(2-methyl-4-pentynyl)oxy]silane；(R)-tert-butyldimethyl(2-methylpent-4-ynyloxy)silane；tert-butyl-dimethyl-[(2R)-2-methylpent-4-ynoxy]silane
• CAS: 152755-20-9
• 化学式: C₁₂H₂₄OSi
• 分子量: 212.407
• InChiKey: XBMNHARYDARQAO-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4R)-5-(tert-butyldimethylsiloxy)-4-methylpent-1-yne 在 zirconocene dichloride 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 正丁基锂 、 碘 、 叔丁基锂 、 对甲苯磺酸 、 copper(II) sulfate 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 37.75h， 生成 (2R,4S,6S)-2-<(5'R,2'E)-6'-hydroxy-3',5'-dimethylhex-2'-enyl>-1,7-dioxaspiro<5.5>undecan-4-ol
  参考文献：
  名称：

  Khandekar, Girish; Robinson, Gareth C.; Stacey, Nicholas A., Journal of the Chemical Society. Perkin transactions I, 1993, # 13, p. 1507 - 1520

  摘要：

  DOI：
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (2R)-2-甲基戊-4-炔-1-醇 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 生成 (4R)-5-(tert-butyldimethylsiloxy)-4-methylpent-1-yne
  参考文献：
  名称：

  The First Total Synthesis of (+)-Ratjadone

  摘要：

  The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis of structural analogues for biological target identification.

  DOI：

  10.1021/jo005768g

文献信息

• Synthesis of Optically Active 6-Alkynyl- and 6-Alkylpurines as Cytokinin Analogs and Inhibitors of 15-Lipoxygenase; Studies of Intramolecular Cyclization of 6-(Hydroxyalkyn-1-yl)purines
  作者：Tom Christian Berg、Lise-Lotte Gundersen、Aud Berglen Eriksen、Karl E. Malterud

  DOI：10.1002/ejoc.200500417

  日期：2005.12

  Optically active 6-alkynyl- and 6-alkylpurines have been synthesized. These compounds can be regarded as analogs of cytokinin plant growth hormones. The analogs were examined as growth stimulators and as inhibitors of 15-lipoxygenase (15-LO). The (S)-enantiomer of 6-(5-hydroxy-4-methylpent-1-yl)purine exhibited profound growth stimulation activity, especially at low concentrations. 6-(Hydroxyalkyn-1-yl)purines

  已经合成了光学活性的 6-炔基和 6-烷基嘌呤。这些化合物可视为细胞分裂素植物生长激素的类似物。这些类似物被检测为生长刺激剂和 15-脂肪氧化酶 (15-LO) 抑制剂。6-(5-hydroxy-4-methylpent-1-yl) 嘌呤的 (S)-对映异构体表现出强烈的生长刺激活性，尤其是在低浓度下。发现 6-(Hydroxyalkyn-1-yl) 嘌呤通过来自三键羟基的亲核外向攻击而环化。(Z)-异构体在酸性条件下形成。在环化产物中鉴定出植物生长刺激剂和 15-LO 抑制剂。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• On the structure of the Phytophthora α1 mating hormone: synthesis and comparison of four candidate stereoisomers
  作者：Reena Bajpai、Fanglong Yang、Dennis P. Curran

  DOI：10.1016/j.tetlet.2007.09.054

  日期：2007.11

  Two two-compound mixtures of candidate structures for the Phytophthora alpha 1 mating hormone have been synthesized. The mixtures were designed to have differing configurations at C3, but proved to be identical. This suggests that epimerization occurred at C3, and comparison with the data for the natural samples suggest that this is also a mixture of isomers. (c) 2007 Elsevier Ltd. All rights reserved.