(S)-8,8-dimethoxy-2,6-dimethyl-oct-2-ene | 111718-31-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-8,8-dimethoxy-2,6-dimethyl-oct-2-ene
• 英文别名: (-)-citronellal dimethyl acetal；(6S)-8,8-dimethoxy-2,6-dimethyloct-2-ene
• CAS: 111718-31-1
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: SEXUFKWNUNQRSS-NSHDSACASA-N

物化性质

• 沸点：
  70 °C(Press: 0.5 Torr)
• 密度：
  0.857±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-8,8-dimethoxy-2,6-dimethyl-oct-2-ene 在 dimethyl sulfide borane 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以97%的产率得到
  参考文献：
  名称：

  通过多米诺骨牌合成高效合成愈创树倍半萜烯（-）-异愈创木烯

  摘要：

  （-）-异愈创木烯仅以9-10步就可从（S）-香茅醛中制得，且总收率良好。从（S）-香茅醛衍生的醛的三烯炔或二烯二酮复分解和高度非对映选择性的有机催化迈克尔加成反应是关键的转化。

  DOI：

  10.3762/bjoc.15.83
• 作为产物：
  描述：

  (-)-香茅醛 、 原甲酸三甲酯 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到(S)-8,8-dimethoxy-2,6-dimethyl-oct-2-ene
  参考文献：
  名称：

  Highly Efficient Acetalization of Carbonyl Compounds Catalyzed by Aniline–Aldehyde Resin Salts

  摘要：

  本方法描述了使用1 mol%的苯胺-醛树脂盐催化，从相应的醛和酮合成乙烯缩醛和二甲缩醛的温和步骤。此方法同样适用于二芳基酮的二甲缩醛的合成。

  DOI：

  10.1246/cl.150166

文献信息

• Macrocyclic musk compounds—XI
  作者：V.R. Mamdapur、P.P. Pai、K.K. Chakravarti、U.G. Nayak、S.C. Bhattacharyya

  DOI：10.1016/s0040-4020(01)90838-5

  日期：1964.1

  A simple synthesis of (−)-muscone has been developed by using citronellal and oleyl alcohol as the starting materials.

  通过使用香茅醛和油醇作为起始原料，开发了一种简单的（-）-muscone合成方法。
• Preparation, Characterization, and Synthetic Uses of Lanthanide(III) Catalysts Supported on Ion Exchange Resins
  作者：Libing Yu、Depu Chen、Jun Li、Peng George Wang

  DOI：10.1021/jo961933+

  日期：1997.5.1

  Lanthanide(III) catalysts supported on ion exchange resins (Ln-resins) were prepared from Dowex, Amberlite, Amberlyst, and other cation exchange resins. The amount of lanthanides on resin supports was measured through EDTA titration. The results indicated that the lanthanides in aqueous solution exchanged with almost all the cations (H+ or Na+) on the resins to form stable ionic complexes between the lanthanides(III) and the resins. The effects of resin types, resin sizes, and lanthanide salts were investigated with a reaction of indole and hexanal in aqueous solution and with an aldol reaction of benzaldehyde and silyl enol ether in organic solvents. The study found that among ion exchange resins tested Amberlyst XN-1010 and Amberlyst 15 complexed with lanthanides(III) were the most effective catalysts. In addition, the selective Ln-resins were utilized to catalyze acetalization of aldehydes, aldol reaction of formaldehyde or benzaldehyde in aqueous solution, nucleophilic addition to an imine, allylation of an aldehyde, an aza Diels-Alder (DA) reaction, and a ring-opening reaction of an epoxide. Furthermore, glycosylation of alcohol using glucosyl fluoride as a donor was also promoted with the Ln-resin. Thus, this work demonstrated potential uses of lanthanide(III) catalysts supported on ion exchange resins in routine organic reactions.
• Tietze, Lutz F.; Denzer, Horst; Holdgruen, Xenia, Angewandte Chemie, 1987, vol. 99, # 12, p. 1309 - 1310
  作者：Tietze, Lutz F.、Denzer, Horst、Holdgruen, Xenia、Neumann, Manfred

  DOI：——

  日期：——
• Asymmetrization of meso-cyclic ketones using homochiral acetal templates
  作者：Yuji Naruse、Hisashi Yamamoto

  DOI：10.1016/s0040-4020(01)89790-8

  日期：——
• TIETZE, LUTZ F.;DENZER, HORST;HOLDGRUN, XENIA;NEUMANN, MANFRED, ANGEW. CHEM., 99,(1987) N 12, 1309-1310
  作者：TIETZE, LUTZ F.、DENZER, HORST、HOLDGRUN, XENIA、NEUMANN, MANFRED

  DOI：——

  日期：——