4-methoxy dec-1-ene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxy dec-1-ene
• 英文别名: 4-Methoxy-1-decene；4-methoxydec-1-ene
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: HQQOSKLPOWPXMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methoxy dec-1-ene 在 sodium tetrahydroborate 、 重铬酸吡啶 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.5h， 生成 4-methoxydecanoic acid
  参考文献：
  名称：

  外消旋和（R）和（S）-4-甲氧基链烷酸的全合成及其抗真菌活性

  摘要：

  已完成外消旋和立体选择性[（R）和（S）]形式的4-甲氧基癸酸和4-甲氧基十一烷酸的全合成。为了立体选择性地合成化合物（S）和（R）-BINOL，已使用配合物生成所需的手性中心。已经研究了这些化合物对不同生物的抗真菌活性，结果令人印象深刻。比较了外消旋和立体选择性形式的化合物的活性。（R）-4-甲氧基癸酸被发现是最有效的（MIC：白色念珠菌MTCC 227，白色念珠菌MTCC 4748，巴西曲霉（Aspergillus brasiliensis）的MIC：0.019 mg / mL（niger）MTCC 281和Issatchenkia Orientalis MTCC 3020）。

  DOI：

  10.1016/j.ejmech.2011.04.045
• 作为产物：
  描述：

  庚醛二甲基缩醛 在 三氟化硼乙醚 、 silver perchlorate 、 calcium carbonate 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-methoxy dec-1-ene
  参考文献：
  名称：

  Lewis Acid Activated Reactions of Mixed (O,Se) Acetals with Allyltrimethylsilane and Allyltributylstannane

  摘要：

  On the basis of preferential complexation of oxygen or selenium atoms by different Lewis acids, it was expected that, depending on the Lewis acid employed, the title reactions would lead to selective formation of homoallyl ethers or homoallyl selenides. This has not been confirmed by experiment: in almost all the reactions tried homoallyl ethers largely predominated; or were the exclusive allylation products, even when strongly oxygenophilic Lewis acids such as TiCl4 were used. In the cases of the latter type of Lewis acids, the results observed with (O,Se) and a couple of(O,S) mixed acetals are-interpreted in terms of two major factors operating in opposite directions. H-1 NMR data of a mixture of TiCl4 and (O,Se) acetal indicate that preferential (but not exclusive) complexation of the oxygen moiety takes place indeed. However, because of the much stronger C-O bond as compared to the C-Se bond, this latter.(also activated by the Lewis acid to some extent) undergoes cleavage by allyl metals to give homoallyl ethers as predominating products. In contrast with BF3 . OEt(2), boron trichloride and boron tribromide were found to react with (O,Se) acetals to give the corresponding alpha-halo selenides, which in turn were cleanly transformed into homoallyl selenides on reaction with allyltrimethylsilane in the presence of tin tetrachloride.

  DOI：

  10.1021/jo00124a029

文献信息

• Total synthesis of racemic and (R) and (S)-4-methoxyalkanoic acids and their antifungal activity
  作者：Biswanath Das、Digambar Balaji Shinde、Boddu Shashi Kanth、Avijeet Kamle、C. Ganesh Kumar

  DOI：10.1016/j.ejmech.2011.04.045

  日期：2011.7

  The total synthesis of 4-methoxydecanoic acid and 4-methoxyundecanoic acid in racemic and stereoselective [(R) and (S)] forms has been accomplished. For stereoselective synthesis of the compounds (S) and (R)-BINOL complexes have been used to generate the required chiral centres. The antifungal activity of these compounds has been studied against different organisms and the results were found to be impressive

  已完成外消旋和立体选择性[（R）和（S）]形式的4-甲氧基癸酸和4-甲氧基十一烷酸的全合成。为了立体选择性地合成化合物（S）和（R）-BINOL，已使用配合物生成所需的手性中心。已经研究了这些化合物对不同生物的抗真菌活性，结果令人印象深刻。比较了外消旋和立体选择性形式的化合物的活性。（R）-4-甲氧基癸酸被发现是最有效的（MIC：白色念珠菌MTCC 227，白色念珠菌MTCC 4748，巴西曲霉（Aspergillus brasiliensis）的MIC：0.019 mg / mL（niger）MTCC 281和Issatchenkia Orientalis MTCC 3020）。
• Trimethylsilyl bis(fluorosulfonyl)imide: A new catalyst for the reactions of acetals with silyl nucleophiles
  作者：Achla Trehan、Ashwani Vij、Meenakshi Walia、Gurmeet Kaur、R.D. Vermar、Sanjay Trehan

  DOI：10.1016/s0040-4039(00)79323-3

  日期：1993.11

  A new catalyst trimethylsilyl bis(fluorosulfonyl)imide has been prepared for aldol type reactions and allylation of acetals. The catalyst has been found to be more active than trimethylsilyl triflate for the above reactions.

  制备了一种新的三甲基甲硅烷基双（氟磺酰基）亚胺催化剂，用于醛醇缩醛型反应和缩醛的烯丙基化。对于上述反应，发现该催化剂比三氟甲磺酸三甲基甲硅烷基酯更具活性。
• Efficient Brønsted Acid Catalyzed Hosomi-Sakurai Reaction of Acetals
  作者：Benjamin List、Daniela Kampen

  DOI：10.1055/s-2006-950444

  日期：2006.9

  Acetals react with allyltrimethylsilane in the presence of a catalytic amount of sulfonic acids to give the corresponding homoallylic ethers in high yields. The scope of the reaction is broad and both aromatic as well as aliphatic acetals can readily be used.

  在一定量磺酸的催化下，乙缩醛与烯丙基三甲基硅烷发生反应，生成相应的高产率均烯丙基醚。该反应的范围很广，芳香族和脂肪族乙缩醛都可以很容易地使用。
• Bismuth triflate catalyzed allylation of acetals: a simple and mild method for synthesis of homoallyl ethers
  作者：Laura C. Wieland、Herbert M. Zerth、Ram S. Mohan

  DOI：10.1016/s0040-4039(02)00906-1

  日期：2002.5

  The allylation of acetals using allyltrimethylsilane is efficiently catalyzed by bismuth triflate (1.0 mol%). The reaction proceeds smoothly at room temperature to afford the corresponding homoallyl ether in good yield. The mild reaction conditions. the low toxicity of bismuth salts. and the high catalytic efficiency of the system make this procedure particularly attractive for large-scale synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Mayr, Herbert; Gorath, Gorden; Bauer, Bernhard, Angewandte Chemie, 1994, vol. 106, # 7, p. 793 - 794
  作者：Mayr, Herbert、Gorath, Gorden、Bauer, Bernhard

  DOI：——

  日期：——