Triheptylboran | 3244-73-3

• 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: Triheptylboran
• 英文别名: triheptylborane；Tri-n-heptylborane
• CAS: 3244-73-3
• 化学式: C₂₁H₄₅B
• 分子量: 308.399
• InChiKey: UANXIXMBVDNXFA-UHFFFAOYSA-N

物化性质

• 沸点：
  147-152 °C(Press: 0.6 Torr)
• 密度：
  0.776±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.39
• 重原子数：
  22
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  Triheptylboran 在 sodium perborate 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.5h， 生成 1-苯基-1-辛醇
  参考文献：
  名称：

  在镁或锂的存在下，由α，α-二氯芳基甲烷和三烷基硼烷轻松地一锅合成烷基芳基甲醇

  摘要：

  由α，α-二氯芳基甲烷和镁或锂生成的α-氯苄基氯化镁或α-氯苄基锂在室温下与三烷基硼烷在THF中原位反应，用过硼酸钠氧化后以高收率产生相应的烷基芳基甲醇。

  DOI：

  10.1016/s0022-328x(96)06722-8
• 作为产物：
  描述：

  1-庚烯 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 Triheptylboran
  参考文献：
  名称：

  2-Pyrones possessing antimicrobial and cytotoxic activities

  摘要：

  The 2-pyrone sub-unit is found in a number of natural products possessing broad spectrum biological activity. Such compounds are validated as being capable of binding to specific protein domains and able to exert a remarkable range of biological effects. In an effort to identify synthetic 2-pyrones with interesting biological effects, herein we report the synthesis and biological evaluation of 4-substituted-6-methyl-2-pyrones. Synthetic routes to 4-alkyl/alkenyl/aryl/alkynyl-6-methyl-2-pyrones have been developed utilising Sonogashira, Suzuki and Negishi cross-coupling starting from readily available 4-bromo-6-methyl-2-pyrone. Specific conditions for each organometallic protocol were required for successful cross-coupling. In particular, a triethylamine/acetonitrile-base/solvent mixture was crucial to Sonogashira alkynylation of 4-bromo-6-methyl-2-pyrone, whereas thallium carbonate was a mandatory base for the Suzuki cross-coupling of trialkylboranes. The 2-pyrones demonstrate potent inhibitory activity against Bacillus subtilis, Escherichia coli, Staphylococcus aureus, Schizosaccharomyces pombe and Botrytis cinerea. The growth inhibitory activities of selected 2-pyrones were determined in A2780 human ovarian carcinoma and K562 human chronic myelogenous leukaemia cell lines using an in vitro cell culture system (MTT assay). These studies demonstrate that 4-phenylethynyl-, 4-tetrahydropyranylpropargyl ether- and 4-ethynyl-6-methyl-2-pyrones have excellent potential as a new class of anticancer agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.051

文献信息

• Mild Synthesis of Organophosphorus Compounds:  Reaction of Phosphorus-Containing Carbenoids with Organoboranes
  作者：Monika I. Antczak、Jean-Luc Montchamp

  DOI：10.1021/ol800085u

  日期：2008.3.1

  Organoboranes react with phosphorus-containing carbenoids to produce a variety of functionalized organophosphorus compounds under mild conditions. In some cases, selective migration of one group attached to boron can be observed. Phosphonite-borane complexes are introduced as novel synthons for the synthesis of phosphinic esters.

  有机硼烷在温和条件下与含磷类卡宾反应生成多种功能化的有机磷化合物。在某些情况下，可以观察到与硼相连的一组选择性迁移。次膦酸酯-硼烷复合物被引入作为合成次膦酸酯的新型合成子。
• Synthesis of ketones and tertiary alcohols from trialkylboranes. Use of lithium tris(phenylthio)methanide
  作者：Andrew Pelter、J. Madhusudhana Rao

  DOI：10.1039/c39810001149

  日期：——

  The interaction of lithium tris(phenylthio)-methanide with trialkylboranes followed by oxidation allows the production of ketones or tertiary alcohols in good yields under mild conditions.

  三（苯硫基）甲硫基锂与三烷基硼烷的相互作用，然后进行氧化，可以在温和的条件下以高收率生产酮或叔醇。
• Lithium tris(phenylthio)methane for the homologation of trialkylboranes: Convenient syntheses of ketones and t-carbinols
  作者：Andrew Pelter、J.Madhusudhana Rao

  DOI：10.1016/0022-328x(85)87357-5

  日期：1985.4

  Lithium tris(phenylthio)methane is a readily available, cheap reagent for the production of ketones and t-carbinols from trialkylboranes. The scope and limitations of the reactions are indicated as are some of its unique features.

  三（苯硫基）甲烷锂是一种易于获得的廉价试剂，用于从三烷基硼烷生产酮和叔碳醇。指出了反应的范围和局限性及其一些独特特征。
• Alkylation of α,α-dichloroarylmethane with trialkylboranes: Synthesis of alkylarylcarbinols
  作者：George W. Kabalka、Nan-Sheng Li、Su Yu

  DOI：10.1016/0040-4039(95)01870-n

  日期：1995.11

  The alkylation of α,α-dichloroarylmethane with trialkylboranes occurs readily in the presence of t-butyllithium at −78 °C. The reaction affords the corresponding alkylarylcarbinols in good yields after oxidation with sodium perborate.

  α-α-二氯芳基甲烷与三烷基硼烷的烷基化反应容易在叔丁基锂存在下于-78°C进行。用过硼酸钠氧化后，该反应以良好的产率提供相应的烷基芳基甲醇。
• Reactions of α-Boranophosphorus Compounds with Electrophiles: Alkylation, Acylation, and other Reactions
  作者：Monika I. Antczak、Jean-Luc Montchamp

  DOI：10.1021/jo900300c

  日期：2009.5.15

  The homologation of phosphorus carbenoids with organoboranes leads to α-boranophosphorus compounds, which can be further functionalized through reactions with various electrophiles, either directly or after activation to the corresponding borate. A variety of substituted organophosphorus compounds can be obtained in one pot via reaction with many electrophiles. Complex structures are prepared in a

  磷类胡萝卜素与有机硼烷的同源化产生α-硼磷化合物，可通过与各种亲电试剂的反应直接或在活化为相应的硼酸盐后进一步官能化。通过与许多亲电试剂反应，可以在一锅中获得各种取代的有机磷化合物。使用简单的构建块即可一步完成复杂结构的准备。