tert-butyl 2-bromo-4-pentenoate | 39149-84-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl 2-bromo-4-pentenoate
• 英文别名: t-butyl 2-bromo-4-pentenoate；tert-butyl 2-bromopent-4-enoate
• CAS: 39149-84-3
• 化学式: C₉H₁₅BrO₂
• 分子量: 235.121
• InChiKey: FHRNANGNJYOJRI-UHFFFAOYSA-N

物化性质

• 沸点：
  219.3±20.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-bromo-4-pentenoate 在 palladium on activated charcoal 硫酸 、 氢气 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 96.0h， 生成 2,3',6-trihydroxy-4-<1-(carbo-tert-butoxy)-3,4-dihydroxybutoxy>-4'-propoxydihydrochalcone
  参考文献：
  名称：

  Dihydrochalcone sweeteners. A study of the atypical temporal phenomena

  摘要：

  Neohesperidin dihydrochalcone (NHDHC), known since 1963 as an intensely sweet compound, is determined to be 340 +/- 60 (p less than 0.05) times more potent than sucrose. The unusual temporal properties of this material are hypothesized as being due to the effects of metabolism, conformation, chelation, or hydrophobicity. Forty-four analogues are synthesized to test the four hypotheses, none of which are strongly supported. A method of quantitation of temporal characteristics of tastant molecules is developed so as to allow comparison of taste appearance time (AT) and extinction time (ET) of experimental compounds. Four of the new compounds, 40 and 43-45, exhibit high sweetness potencies, ranging from 280 and 440 times sucrose, and may be useful in selected food systems. The temporal taste characteristics remain unimproved over NHDHC, however.

  DOI：

  10.1021/jm00136a011
• 作为产物：
  描述：

  DL-2-氨基-4-戊烯酸 在 4-二甲氨基吡啶 、 氢溴酸 、 N,N'-二环己基碳二亚胺 、 sodium bromide 、 sodium nitrite 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 tert-butyl 2-bromo-4-pentenoate
  参考文献：
  名称：

  镍催化末端炔烃的不对称反选择性硼基烷基化

  摘要：

  炔三键向双键的选择性转化是构建取代烯烃的有效平台。尽管其时空调控已取得重大进展，但实现需要克服多方面选择性问题的多组分对映选择性反应仍然不常见。在这里，我们报告了通过镍催化对末端炔烃进行前所未有的不对称反立体选择性硼基碳官能化。利用廉价的手性二胺配体可以实现末端炔烃、二硼试剂和前手性烷基亲电子试剂的三组分交叉偶联，并具有高水平的区域选择性、立体选择性和对映选择性。该反应提供了一种有效的方案来获得带有α-立体中心的对映体富集的烯基酯，非常实用，并且具有广泛的范围和出色的官能团兼容性。此外，该方法的价值在后续的多种立体保留衍生化和复杂药物分子的立体选择性简明合成中也得到了凸显。

  DOI：

  10.1021/jacs.3c05969

文献信息

• Silver-catalyzed [2,3]-rearrangement of halonium ylides derived from allyl and propargyl halides and alkyl diazoacetates
  作者：Pasupathy Krishnamoorthy、R. Greg Browning、Shreeyukta Singh、Rasapalli Sivappa、Carl J. Lovely、H. V. Rasika Dias

  DOI：10.1039/b608266a

  日期：——

  A silver(I) complex derived from a polyfluorinated tris(pyrazolyl)borate effectively catalyzes carbene transfer to allylic and propargylic halides, leading to the formation of alpha-haloacetate derivatives.

  衍生自多氟化三（吡唑基）硼酸酯的银（I）络合物可有效催化卡宾转移至烯丙基和炔丙基卤化物，导致形成α-卤代乙酸酯衍生物。
• α-Halocarbonyl compounds, I. An efficient preparation of α-bromoesters and α-bromoacids
  作者：Philip L. Stotter、Kenneth A. Hill

  DOI：10.1016/s0040-4039(01)94239-x

  日期：1972.1
• Dihydrochalcone sweeteners. A study of the atypical temporal phenomena
  作者：Grant E. DuBois、Guy A. Crosby、Rebecca A. Stephenson

  DOI：10.1021/jm00136a011

  日期：1981.4

  Neohesperidin dihydrochalcone (NHDHC), known since 1963 as an intensely sweet compound, is determined to be 340 +/- 60 (p less than 0.05) times more potent than sucrose. The unusual temporal properties of this material are hypothesized as being due to the effects of metabolism, conformation, chelation, or hydrophobicity. Forty-four analogues are synthesized to test the four hypotheses, none of which are strongly supported. A method of quantitation of temporal characteristics of tastant molecules is developed so as to allow comparison of taste appearance time (AT) and extinction time (ET) of experimental compounds. Four of the new compounds, 40 and 43-45, exhibit high sweetness potencies, ranging from 280 and 440 times sucrose, and may be useful in selected food systems. The temporal taste characteristics remain unimproved over NHDHC, however.
• Asymmetric <i>anti</i>-Selective Borylalkylation of Terminal Alkynes by Nickel Catalysis
  作者：Chengmi Huang、Dong Wu、Yangyang Li、Guoyin Yin

  DOI：10.1021/jacs.3c05969

  日期：2023.8.30

  diboron reagent, and prochiral alkyl electrophiles with high levels of regio-, stereo-, and enantioselectivities. This reaction provides an efficient protocol to access enantioenriched alkenyl esters bearing an α-stereogenic center, is remarkably practical, and has a broad scope and an outstanding functional group compatibility. In addition, the value of this method has been highlighted in a diversity of

  炔三键向双键的选择性转化是构建取代烯烃的有效平台。尽管其时空调控已取得重大进展，但实现需要克服多方面选择性问题的多组分对映选择性反应仍然不常见。在这里，我们报告了通过镍催化对末端炔烃进行前所未有的不对称反立体选择性硼基碳官能化。利用廉价的手性二胺配体可以实现末端炔烃、二硼试剂和前手性烷基亲电子试剂的三组分交叉偶联，并具有高水平的区域选择性、立体选择性和对映选择性。该反应提供了一种有效的方案来获得带有α-立体中心的对映体富集的烯基酯，非常实用，并且具有广泛的范围和出色的官能团兼容性。此外，该方法的价值在后续的多种立体保留衍生化和复杂药物分子的立体选择性简明合成中也得到了凸显。