12-羟基十二烷醛乙烯缩醛 | 161646-38-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 12-羟基十二烷醛乙烯缩醛
• 英文名称: 12-hydroxydodecanal ethylene acetal
• 英文别名: 2-(11-hydroxyundecyl)-1,3-dioxolane；11-[1,3]dioxolan-2-ylundecan-1-ol；11-(1,3-Dioxolan-2-yl)undecan-1-ol
• CAS: 161646-38-4
• 化学式: C₁₄H₂₈O₃
• 分子量: 244.375
• InChiKey: ARQZLDFEKZXIQP-UHFFFAOYSA-N

物化性质

• 沸点：
  344.5±17.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  12-羟基十二烷醛乙烯缩醛 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以43%的产率得到12-bromododecanal ethylene acetal
  参考文献：
  名称：

  Sex Pheromone of Chilo Suppressalis: Efficient Syntheses of (Z)-11-Hexadecenal, (Z)-13-Octadecenal And (Z)-9-Hexadecenal

  摘要：

  The constituents of the sex attractant pheromone of Chilo suppressalis: (Z)-11-Hexedecenal 1, (Z)-13-octadecenenal 2 and (Z)-9-Hexadecenal 3 have been synthesized as their ethylene acetals 19, 15 and 13, in six steps from easily available compounds. The synthetic methodology can be applied to preparative scale.

  DOI：

  10.1080/00397919608004544
• 作为产物：
  描述：

  12,12-dimethoxydodecanoic acid methyl ester 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.5h， 生成 12-羟基十二烷醛乙烯缩醛
  参考文献：
  名称：

  Sex Pheromone of Chilo Suppressalis: Efficient Syntheses of (Z)-11-Hexadecenal, (Z)-13-Octadecenal And (Z)-9-Hexadecenal

  摘要：

  The constituents of the sex attractant pheromone of Chilo suppressalis: (Z)-11-Hexedecenal 1, (Z)-13-octadecenenal 2 and (Z)-9-Hexadecenal 3 have been synthesized as their ethylene acetals 19, 15 and 13, in six steps from easily available compounds. The synthetic methodology can be applied to preparative scale.

  DOI：

  10.1080/00397919608004544

文献信息

• Tandem Hydroformylation/Hydrogenation of Alkenes to Normal Alcohols Using Rh/Ru Dual Catalyst or Ru Single Component Catalyst
  作者：Kohei Takahashi、Makoto Yamashita、Kyoko Nozaki

  DOI：10.1021/ja307998h

  日期：2012.11.14

  The catalyst system for tandem hydroformylation/hydrogenation of terminal alkenes to the corresponding homologated normal alcohol was developed. The reaction mechanism for the Rh/Ru dual catalyst was investigated by real-time IR monitoring experiments and (31)P NMR spectroscopy, which proved the mutual orthogonality of Rh-catalyzed hydroformylation and Ru-catalyzed hydrogenation. Detailed investigation

  开发了用于末端烯烃串联加氢甲酰化/加氢生成相应同系正醇的催化剂体系。通过实时红外监测实验和(31)P NMR光谱研究了Rh/Ru双催化剂的反应机理，证明了Rh催化加氢甲酰化和Ru催化加氢的相互正交性。在 H(2)/CO 压力下 Ru 催化十一醛加氢的详细调查阐明了与 H(2) 下加氢的不同动力学，并为在 H(2)/CO 气氛下设计更活跃的加氢催化剂提供了线索。还报道了单独的 Ru 催化的正常选择性加氢甲酰化/氢化。
• Tandem Rhodium-Catalyzed Hydroformylation-Hydrogenation of Alkenes by Employing a Cooperative Ligand System
  作者：Daniela Fuchs、Géraldine Rousseau、Lisa Diab、Urs Gellrich、Bernhard Breit

  DOI：10.1002/anie.201108946

  日期：2012.2.27

  action: A multifunctional rhodium catalyst system enables the simultaneous catalysis of two distinct transformations, hydroformylation of an alkene and reduction of an aldehyde, in a highly selective manner. This one‐pot/two‐step process is controlled by the cooperative action of two different supramolecular ligand systems and transforms terminal alkenes into C1‐chain‐elongated linear alcohols.

  双重作用：多功能铑催化剂体系能够以高度选择性的方式同时催化两个不同的转化，即烯烃的加氢甲酰化和醛的还原。这一单步/两步过程受两种不同的超分子配体系统的协同作用控制，并将末端烯烃转化为C 1链加长的线性醇。
• Components of the Sex Pheromone of Chilo Supressalis: Efficient Syntheses of (Z)-11-Hexadecenal and (Z)-13-Octadecenal
  作者：S. Gil、M. A. Lázaro、R. Mestres、F. Millan、M. Parra

  DOI：10.1080/00397919508011366

  日期：1995.2

  Abstract (Z)-11-Hexedecenal 1a and (Z)-13-octadecenenal 2a, components of the sex attractant pheromone of Chilo supressalis, have been synthesized as their ethylene acetals 1b and 2b from cyclododecanone 3, through intermediacy of the C12 ω functionalized acetals 8 and 12.

  摘要 (Z)-11-十六烯醛 1a 和 (Z)-13-十八烯烯醛 2a 是压花树性诱剂信息素的组分，已通过 C12 ω 功能化的中间体从环十二酮 3 合成为它们的乙烯缩醛 1b 和 2b。缩醛 8 和 12。
• Alkyl- and Arylation of Oxacyclic Ethers with Triethylsilyl Triflate—2,4,6-Collidine—Gilman Reagent Combination: Remarkable Discrimination of Two Ether Oxygens
  作者：Hiromichi Fujioka、Takuya Ohnaka、Takashi Okitsu、Ozora Kubo、Kazuhisa Okamoto、Yoshinari Sawama、Yasuyuki Kita

  DOI：10.3987/com-06-s(k)46

  日期：——

  The alkylation reaction of oxacyclic ethers such as THP-ethers, THF-ethers, etc., has been developed. The treatment of oxacyclic ether with TESOTf and 2,4,6-collidine gives the collidinium salt intermediate obtained by the reaction of the cyclic oxygen atom. The addition of Gilman reagent to the mixture gives the alkylated product. The reaction proceeds with high chemoselectivity though there are two different oxygen atoms in the oxacyclic ethers.
• Sex Pheromone of Chilo Suppressalis: Efficient Syntheses of (Z)-11-Hexadecenal, (Z)-13-Octadecenal And (Z)-9-Hexadecenal
  作者：Salvador Gil、Miguel A. LáAzaro、Ramóan Mestres、Margarita Parra

  DOI：10.1080/00397919608004544

  日期：1996.6

  The constituents of the sex attractant pheromone of Chilo suppressalis: (Z)-11-Hexedecenal 1, (Z)-13-octadecenenal 2 and (Z)-9-Hexadecenal 3 have been synthesized as their ethylene acetals 19, 15 and 13, in six steps from easily available compounds. The synthetic methodology can be applied to preparative scale.