(+)-(S)-3-methyl-1-pentyne | 2868-07-7

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: (+)-(S)-3-methyl-1-pentyne
• 英文别名: (+)(S)-3-methyl-1-pentyne；(S)-3-methyl-1-pentyne；(S)-3-methyl-pent-1-yne；(+)-(5)-3-Methyl-pent-1-in；(S)-3-Methyl-pent-1-in；(S)-3-Methyl-1-pentin；(S)-3-Methylpent-1-yne；(3S)-3-methylpent-1-yne
• CAS: 2868-07-7
• 化学式: C₆H₁₀
• 分子量: 82.1454
• InChiKey: PLHJCCHSCFNKCC-ZCFIWIBFSA-N

物化性质

• 沸点：
  60.0±8.0 °C(Predicted)
• 密度：
  0.735±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (+)-(S)-3-methyl-1-pentyne 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide potassium permanganate 、 lithium aluminium tetrahydride 作用下， 以 三乙胺 为溶剂， 反应 83.0h， 生成 S-(-)-2-甲基-1-丁醇
  参考文献：
  名称：

  Chiral acetylenes as synthetic intermediates. 4. Synthesis and chiroptical properties of optically active .alpha.,.beta.-acetylenic ketones

  摘要：

  DOI：

  10.1021/jo00173a021
• 作为产物：
  描述：

  (S)-3-甲基戊-1-烯 在 氢氧化钾 、 溴 作用下， 以 氯仿 为溶剂， 生成 (+)-(S)-3-methyl-1-pentyne
  参考文献：
  名称：

  Synthesis of Some 1-Alkynes Containing an Optically Active sec-Butyl Group

  摘要：

  DOI：

  10.1021/jo01343a053

文献信息

• 1,4-Pentenyne as a Five-Carbon Synthon for Efficient and Selective Syntheses of Natural Products Containing 2,4-Dimethyl-1-penten-1,5-ylidene and Related Moieties by Means of Zr-Catalyzed Carboalumination of Alkynes and Alkenes
  作者：Gangguo Zhu、Ei-ichi Negishi

  DOI：10.1002/chem.200701512

  日期：2008.1

  Two highly efficient protocols for enantioselective synthesis of 2,4-dimethyl-1-penten-1,5-ylidene derivatives involve the combined use of the Zr-catalyzed methylalumination of alkynes (ZMA) and the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA). The ZMA/ZACA protocol has been applied to the synthesis of a nafuredin intermediate 14 and a potential intermediate 18 for milbemycin beta 3,

  对映选择性合成2,4-二甲基-1-戊烯-1,5-亚烷基衍生物的两个高效方案涉及Zr催化的炔烃甲基铝化（ZMA）和Zr催化的烯烃不对称碳铝化（ZACA）的组合使用）。ZMA / ZACA协议已被用于合成那富瑞丁中间体14和米尔贝霉素beta 3的潜在中间体18，而ZACA / ZMA协议已被应用于合成（-）-bafilomycin A（1）中间体25岁
• First total synthesis of the whole series of the antiostatins A and B
  作者：Kerstin E. Knott、Stefan Auschill、Anne Jäger、Hans-Joachim Knölker

  DOI：10.1039/b821039j

  日期：——

  The first synthesis of the whole antiostatin family is described by using an iron-mediated carbazole synthesis, regioselective nitration at C-4 and establishing 5-isobutyl-1-nitrobiuret as a reagent for introduction of the antiostatin B side chain at C-4.

  首次合成整个抗胃抑制素家族的方法是通过铁介导的咔唑合成、在C-4位置的区域选择性硝化，以及将5-异丁基-1-硝基氨基甲酸酯作为试剂引入C-4位置的抗胃抑制素B侧链。
• Chiral acetylenes as synthetic intermediates—II
  作者：Giampaolo Giacomelli、Luciano Lardicci、Carlo Bertucci、Anna Maria Caporusso

  DOI：10.1016/0040-4020(78)80111-2

  日期：1978.1

  The synthesis and the physical properties of some optically active 1,4-dialkylbuta-1,3-dienes are reported. The synthetic processes employed were essentially stereospecific. NMR, UV and CD spectra of these compounds provide information on the main conformation of the conjugated diene system, which was shown to be s-trans planar.

  报道了一些光学活性的1，4-二烷基丁-1，3-二烯的合成和物理性质。所使用的合成方法基本上是立体定向的。这些化合物的NMR，UV和CD光谱提供了有关共轭二烯系统主要构象的信息，该构象显示为s-反式平面。
• Silylformylation of Chiral 1-Alkynes, Catalysed by Solvated Rhodium Atoms
  作者：Laura Antonella Aronica、Silvia Terreni、Anna Maria Caporusso、Piero Salvadori

  DOI：10.1002/1099-0690(200111)2001:22<4321::aid-ejoc4321>3.0.co;2-t

  日期：2001.11

  Solvated rhodium atoms, prepared by the metal vapour synthesis technique, promote the silylformylaton reaction of variously substituted alkynes (RRCH)-R-1-C-2(CH2)(n)C equivalent to CH, with catalytic activities comparable with and even higher than more common species such as Rh-4(CO)(12). Z-Silylalkenals are exclusively formed in high yields (60-95%) indicating syn addition both of CO and of the silane (Me2PhSiH) to the triple bond, The chemoselectivity of the process (silylformylation vs. hydrosilylation) is highly affected by the amount of catalyst employed (mmol of Rh species with respect to the alkyne reagent), by the steric requirements of the acetylenic substrates and by the hydrosilane/alkyne molar ratio. When optically active acetylenes are treated in the presence of Me2PhSiH under carbon monoxide pressure, the silylformylation reaction occurs with total retention of stereochemistry of the stereogenic centre, even if it is at the alpha -position of the unsaturated moiety, to afford enantiomerically enriched beta -silylalkenals.
• Caporusso, Anna Maria; Zoppi, Alessandra; Settimo, Federico Da, Gazzetta Chimica Italiana, 1985, vol. 115, # 5, p. 293 - 296
  作者：Caporusso, Anna Maria、Zoppi, Alessandra、Settimo, Federico Da、Lardicci, Luciano

  DOI：——

  日期：——