methyl 3-hydroxy-2,2-dimethyldodecanoate

• 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: methyl 3-hydroxy-2,2-dimethyldodecanoate
• 化学式: C₁₅H₃₀O₃
• 分子量: 258.401
• InChiKey: OZYOIJAARNOGCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-hydroxy-2,2-dimethyldodecanoate 在 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 methyl 3-[(dimethoxyphosphoryl)methoxy]-2,2-dimethyldodecanoate
  参考文献：
  名称：

  Method for the Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin-, Dihydrofuran- and Pyrrolidin-3-ones and Its Application to the Synthesis of (±)-Pseudodeflectusin

  摘要：

  Highly substituted four- and five-membered heterocycles were prepared starting with O,P- and N,P-acetals by using a one-pot method involving base induced cyclization and a Horner-Wadsworth-Emmons (HWE) olefination reaction. Divergent synthesis of various heterocycles was achieved by using this method and transformations of the alkenyl group in the products of these processes were exemplified. Finally, a short and efficient synthesis of (+/-)-pseudodeflectusin based on the new methodology was achieved.

  DOI：

  10.1021/ol302096j
• 作为产物：
  描述：

  癸醛 、 异丁酸甲酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.75h， 以83%的产率得到methyl 3-hydroxy-2,2-dimethyldodecanoate
  参考文献：
  名称：

  Method for the Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin-, Dihydrofuran- and Pyrrolidin-3-ones and Its Application to the Synthesis of (±)-Pseudodeflectusin

  摘要：

  Highly substituted four- and five-membered heterocycles were prepared starting with O,P- and N,P-acetals by using a one-pot method involving base induced cyclization and a Horner-Wadsworth-Emmons (HWE) olefination reaction. Divergent synthesis of various heterocycles was achieved by using this method and transformations of the alkenyl group in the products of these processes were exemplified. Finally, a short and efficient synthesis of (+/-)-pseudodeflectusin based on the new methodology was achieved.

  DOI：

  10.1021/ol302096j

文献信息

• Practical aldol reaction of trimethylsilyl enolate with aldehyde catalyzed by N-methylimidazole as a Lewis base catalyst
  作者：Hisahiro Hagiwara、Hideyuki Inoguchi、Masakazu Fukushima、Takashi Hoshi、Toshio Suzuki

  DOI：10.1016/j.tetlet.2006.05.074

  日期：2006.7

  Aldol reaction of trimethylsilyl enolate with aldehyde proceeded in the presence of a catalytic amount of a Lewis base, N-methylimidazole, and lithium chloride in DMF at room temperature. Not only aryl aldehyde but also alkyl aldehyde provided the aldol product in satisfactory yields. The reaction was mild enough to apply to the aldehyde having HO, AcO, THPO, TBDMSO, MeS, pyridyl or olefinic group

  在室温下，在DMF中在催化量的路易斯碱，N-甲基咪唑和氯化锂的存在下，进行烯丙基三甲基甲硅烷基酯与醛的醛醇缩合反应。不仅芳基醛而且烷基醛都以令人满意的产率提供了羟醛产物。该反应足够温和以适用于具有HO，AcO，THPO，TBDMSO，MeS，吡啶基或烯基的醛。微波辐射加速了反应。
• Aldol Reaction of Trimethylsilyl Enolate with Aldehyde Catalyzed by Pyridine<i>N</i>-Oxide as a Lewis Base Catalyst
  作者：Hisahiro Hagiwara、Hideyuki Inoguchi、Masakazu Fukushima、Takashi Hoshi、Toshio Suzuki

  DOI：10.1055/s-2005-872664

  日期：——

  Aldol reaction of trimethylsilyl enolate with aldehydes proceeded in the presence of a catalytic amount of a Lewis base, pyridine N-oxide, and lithium chloride in DMF at room temperature. Not only aryl aldehydes but also alkyl aldehydes provided the aldol products in satisfactory yields. The reaction was mild enough to apply to aldehydes having HO, AcO, THPO, TBDMSO, MeS, pyridyl, or olefinic groups

  三甲基甲硅烷基烯醇酯与醛的羟醛反应在催化量的路易斯碱、吡啶N-氧化物和氯化锂的存在下在DMF中在室温下进行。不仅芳基醛而且烷基醛都以令人满意的产率提供醛醇产物。该反应足够温和以适用于具有 H2O、AcO、THPO、TBDMSO、MeS、吡啶基或烯烃基团的醛。
• Doucet, Henri; Parrain, Jean-Luc; Santelli, Maurice, Synlett, 2000, # 6, p. 871 - 873
  作者：Doucet, Henri、Parrain, Jean-Luc、Santelli, Maurice

  DOI：——

  日期：——