(Z)-dec-5-enedial | 73125-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-dec-5-enedial
• 英文别名: dec-5c-enedial
• CAS: 73125-67-4
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: BBOMIRMGXCBPQE-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-dec-5-enedial 在 sodium tetrahydroborate 、 水 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以97%的产率得到5(Z)-decene-1,10-diol
  参考文献：
  名称：

  Enantioselective Haloetherification by Asymmetric Opening of meso-Halonium Ions

  摘要：

  A new approach to enantioselective haloetherification reactions via desymmetrization of in situ-generated meso-halonium ions is described. The combination of N-haloamides as a halogen source and sodium salts of chiral phosphoric acids as catalysts can be used for the cyclization of symmetrical ene-diol substrates, yielding the haloetherification products under practical conditions in enantioenriched form.

  DOI：

  10.1021/ol1028805
• 作为产物：
  描述：

  1,5-环辛二烯 在 盐酸 、 potassium tert-butylate 、 水 、 双氧水 、 ortho-tungstic acid 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (Z)-dec-5-enedial
  参考文献：
  名称：

  Enantioselective Haloetherification by Asymmetric Opening of meso-Halonium Ions

  摘要：

  A new approach to enantioselective haloetherification reactions via desymmetrization of in situ-generated meso-halonium ions is described. The combination of N-haloamides as a halogen source and sodium salts of chiral phosphoric acids as catalysts can be used for the cyclization of symmetrical ene-diol substrates, yielding the haloetherification products under practical conditions in enantioenriched form.

  DOI：

  10.1021/ol1028805

文献信息

• Macrocyclic Ring Closure of OH-assistedPrins Reaction. A new and efficient synthesis of (R,S)-muscone
  作者：Karl H. Schulte-Elte、Arnold Hauser、G�nther Ohloff

  DOI：10.1002/hlca.19790620817

  日期：1979.12.12

  macrocyclic ring closure has been developed. The monoacetal 4 of (Z,E)-4,8-dodecadienedial (3), easily obtainable from (Z,E,E)-1,5,9-cyclododecatriene (2), is treated with methallylmagnesium chloride, and the resulting C16-precursor 5 is subjected to acid-catalyzed cyclization in dilute (⩽1%) solutions. This results in formation of the bicyclic dihydropyran derivatives 6 which directly yield muscone (1) on heating

  已开发出一种新的策略，用于使用大环封闭的OH辅助Prins反应合成Muscone （1）。易于从（Z，E，E）-1,5,9-环十二碳三烯（2）获得的（Z，E）-4,8-​​十二二烯醛（3）的单缩醛4用甲基烯丙基氯化镁处理，得到将C 16前体5在稀（约1％）溶液中进行酸催化的环化反应。这导致直接产生麝香酮（1）的双环二氢吡喃衍生物6的形成用饱和氢的贵金属催化剂加热。五步途径采用常规步骤中容易获得的原料，并具有极佳的总收率（约40％）。大环成环的这一新原理也已成功地用于制备3-甲基环翠烷酮（34），并且通常应适用于其他合适的环系统。
• First Total Synthesis and Absolute Configuration of Keramamine C
  作者：Jun'ichi Kobayashi、Haruaki Ishiyama、Yuta Mori、Takashi Matsumoto

  DOI：10.3987/com-12-s(n)123

  日期：——

  Asymmetric first total synthesis of keramamine C, a tetrahydro-beta-carboline alkaloid from an Okinawan marine sponge Amphimedon sp., has been accomplished with the Bischler-Napieralski reaction and the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of keramamine C was elucidated to be 1R from comparison of the H-1 and C-13 NMR, CD spectral data and [alpha](D), values of synthetic and natural keramamine C, respectively.
• Efficient Synthesis of Chiral 2,2′-Bipyrrolidines by an <i>anti</i>-Selective Alkene Diamination
  作者：Christian H. Müller、Roland Fröhlich、Constantin G. Daniliuc、Ulrich Hennecke

  DOI：10.1021/ol302855z

  日期：2012.12.7

  The rapid and efficient construction of complex chiral bicyclic amines is possible using a novel alkene diamination reaction. Electrophilic iodinating agents promote the intramolecular anti-selective diamination of alkenes and allow the efficient synthesis of chiral amines such as trans-bipyrrolidines.
• Enantioselective Haloetherification by Asymmetric Opening of <i>meso</i>-Halonium Ions
  作者：Ulrich Hennecke、Christian H. Müller、Roland Fröhlich

  DOI：10.1021/ol1028805

  日期：2011.3.4

  A new approach to enantioselective haloetherification reactions via desymmetrization of in situ-generated meso-halonium ions is described. The combination of N-haloamides as a halogen source and sodium salts of chiral phosphoric acids as catalysts can be used for the cyclization of symmetrical ene-diol substrates, yielding the haloetherification products under practical conditions in enantioenriched form.