1-tert-butyl-bicyclo<1.1.1>pentane | 125642-43-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: 1-tert-butyl-bicyclo<1.1.1>pentane
• 英文别名: 1-tert-butylbicyclo<1.1.1>pentane；1-t-butylbicyclo<1.1.1>pentane；3-t-butylbicyclo<1.1.1>pentane；3-tert-butyl-1-bicyclo[1.1.1]pentane；3-t-Butylbicyclo[1.1.1]pentane；1-tert-butylbicyclo[1.1.1]pentane
• CAS: 125642-43-5
• 化学式: C₉H₁₆
• 分子量: 124.226
• InChiKey: XTGLSVYONNQGHB-UHFFFAOYSA-N

物化性质

• 沸点：
  90 °C
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  3.0
• 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

反应信息

• 作为反应物：
  描述：

  1-tert-butyl-bicyclo<1.1.1>pentane 在 lead(IV) acetate 盐酸 、 lithium aluminium tetrahydride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 (2R)-2-amino-2-{3-tert-butylbicyclo[1.1.1]pentan-1-yl}acetic acid
  参考文献：
  名称：

  具有双环[1.1.1]戊烷部分的手性氨基酸的合成及其掺入线性和环状抗菌肽中。

  摘要：

  描述了带有双环[1.1.1]戊烷部分的亲脂手性氨基酸1的合成。通过固相肽合成制备含有1个而不是一个或两个色氨酸残基的Arg-Arg-Xaa-Yaa-Arg-Phe型线性和环状六肽，并讨论了所得肽的抗菌和溶血活性。

  DOI：

  10.1039/b702134h
• 作为产物：
  描述：

  1-tert-butyl-3-(trimethylsilyl)bicyclo[1.1.1]pentane 生成 1-tert-butyl-bicyclo<1.1.1>pentane
  参考文献：
  名称：

  DELLA, ERNEST W.;TAYLOR, DENNIS K.;TSANAKTSLDLS, JOHN, TETRAHEDRON LETT. , 31,(1990) N6, C. 5219-5220

  摘要：

  DOI：

文献信息

• γ-Dissociations of 3-alkylbicyclo[1.1.1]pent-1-yl radicals into [1.1.1]propellane and alkyl radicals: verification of a theoretical prediction
  作者：John C. Walton、Lewis Whitehead

  DOI：10.1039/a808744j

  日期：——

  The γ-dissociations of 3-substituted bicyclo[1.1.1]pent-1-yl radicals and cyclobutyl radicals were investigated by abinitio SCF MO (HF, MP2, MP3 and MP4/6–31G*) and density functional methods (B3LYP/6–31G*). The transition states were found to resemble the product alkyl radical and [1.1.1]propellane or bicyclo[1.1.0]butane. Calculated endothermicities and energy barriers were comparatively low for loss of the t-butyl radical from the 3-t-butylbicyclo[1.1.1]pent-1-yl radical, which suggested that this dissociation would be significant under laboratory conditions. The dissociation was verified experimentally by means of the reaction of 1-iodo-3-t-butylbicyclo[1.1.1]pentane with tributyltin hydride. Arrhenius parameters for this dissociation were determined by end product analysis. The SCF MO and density functional calculations resulted in much higher endothermicities and energy barriers for γ-dissociations of cyclobutyl radicals, hence neither the formation of bicyclo[1.1.0]butane nor alkyl radical addition to this bicyclic compound was predicted to be important.

  通过从头算SCF MO（HF、MP2、MP3和MP4/6-31G*）和密度泛函方法（B3LYP/6-31G*），研究了3-取代双环[1.1.1]戊-1-基自由基和环丁基自由基的γ-解离。过渡态被发现类似于产物烷基自由基和[1.1.1]螺旋烷或双环[1.0.0]丁烷。计算得出，从3-叔丁基双环[1.1.1]戊-1-基自由基中失去叔丁基自由基的反应热和能垒相对较低，这表明在实验室条件下这种解离将十分显著。通过1-碘-3-叔丁基双环[1.1.1]戊烷与三丁基锡氢的反应，实验验证了这一解离。通过最终产物分析确定了该解离的阿伦尼乌斯参数。SCF MO和密度泛函计算结果表明，环丁基自由基的γ-解离反应热和能垒要高得多，因此预测双环[1.1.0]丁烷的形成或烷基自由基对该双环化合物的加成都不重要。
• Reactions of [1.1.1]propellane
  作者：Kenneth B. Wiberg、Sherman T. Waddell

  DOI：10.1021/ja00162a022

  日期：1990.3

  The free radical addition reactions of [1.1.1] propellane (1) are described in some detail and allowed the preparation of a wide variety of 1,3-disubstituted bicyclo [1.1.1.] pentanes. The reaction of 1 with free radicals was more rapid than that of bicyclo [1.1.0] butane (2), whereas bicyclo [2.1.0] pentane (3) was relatively inert

  [1.1.1] 推进烷 (1) 的自由基加成反应进行了一些详细的描述，并允许制备各种 1,3-二取代双环 [1.1.1.] 戊烷。1 与自由基的反应比双环 [1.1.0] 丁烷 (2) 更快，而双环 [2.1.0] 戊烷 (3) 相对惰性
• Unusual bridgehead reactivity: Formation of [1.1.1]Propellane by 1,3-dehydrobromination of 1-bromobicyclo[1.1.1]Pentane.
  作者：Ernest W. Della、Dennis K. Taylor、John Tsanaktsidis

  DOI：10.1016/s0040-4039(00)97847-x

  日期：1990.1

  The reaction between -butyllithium and 1-bromobicyclo[1.1.1]pentane is characterised by 1,3-dehydrobromination and gives [1.1.1]propellane . In the presence of -butyllithium, undergoes ring-opening and yields 3--butylbicyclo[l.l.1]pentyllithium .

  -丁基锂与1-溴二环[1.1.1]戊烷之间的反应的特征在于1，3-脱氢溴化，得到[1.1.1]丙炔。在-丁基锂的存在下，进行开环并产生3--丁基双环[III]戊基锂。
• Synthesis of a chiral amino acid with bicyclo[1.1.1]pentane moiety and its incorporation into linear and cyclic antimicrobial peptides
  作者：Stephan Pritz、Michael Pätzel、Günter Szeimies、Margitta Dathe、Michael Bienert

  DOI：10.1039/b702134h

  日期：——

  The synthesis of the lipophilic chiral amino acid 1 bearing the bicyclo[1.1.1]pentane moiety is described. Linear and cyclic hexapeptides of the type Arg-Arg-Xaa-Yaa-Arg-Phe containing 1 instead of one or two tryptophan residues are prepared by solid phase peptide synthesis and the antimicrobial and hemolytic activity of the peptides obtained are discussed.

  描述了带有双环[1.1.1]戊烷部分的亲脂手性氨基酸1的合成。通过固相肽合成制备含有1个而不是一个或两个色氨酸残基的Arg-Arg-Xaa-Yaa-Arg-Phe型线性和环状六肽，并讨论了所得肽的抗菌和溶血活性。
• DELLA, ERNEST W.;TAYLOR, DENNIS K.;TSANAKTSLDLS, JOHN, TETRAHEDRON LETT. , 31,(1990) N6, C. 5219-5220
  作者：DELLA, ERNEST W.、TAYLOR, DENNIS K.、TSANAKTSLDLS, JOHN

  DOI：——

  日期：——