acetic acid-(1-hexyl-but-3-enyl ester) | 2833-33-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: acetic acid-(1-hexyl-but-3-enyl ester)
• 英文别名: Essigsaeure-(1-hexyl-but-3-enylester)；1-decene-4-ol acetate；1-decene-4-acetate；4-Acetoxy-1-decene；dec-1-en-4-yl acetate
• CAS: 2833-33-2
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: GGZUNFKKBLFIGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  102-103 °C(Press: 12 Torr)
• 密度：
  0.879±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  acetic acid-(1-hexyl-but-3-enyl ester) 生成 (+-)-5-hydroxy-undec-2t-enoic acid ethyl ester
  参考文献：
  名称：

  Dolezal,S., Collection of Czechoslovak Chemical Communications, 1965, vol. 30, p. 2638 - 2644

  摘要：

  DOI：
• 作为产物：
  描述：

  庚醛 在 锰 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 生成 acetic acid-(1-hexyl-but-3-enyl ester)
  参考文献：
  名称：

  有机锰（II）试剂XX：锰介导的Barbier和Reformatsky样反应是制备均丙醇和β-乙酰氧基酯的有效途径

  摘要：

  烯丙基卤化物和α-溴酸酯与锰金属在乙酸乙酯中反应；如果将催化量的氯化锌加入到反应混合物中，则THF也可以用作溶剂。当反应在各种醛或酮的存在下进行时，在制备条件下可获得极好的1,2-加成产物收率。

  DOI：

  10.1016/s0040-4039(00)70700-3

文献信息

• Synthesis of Highly Functionalized δ-Lactone-Fused Cyclopentanoids
  作者：Faiz Khan、K. Krishnakumar、Ch. Sudheer

  DOI：10.1055/s-2007-965948

  日期：2007.4

  A short and efficient route to δ-lactone-fused cyclopentanoids starting from the easily accessible Diels-Alder adducts between homoallylic alcohol acetates and 1,2,3,4-tetrachloro-5,5-dimethoxycyclopenta-1,3-diene is reported. Since homoallyl alcohols were derived from the corresponding aldehydes RCHO (R = alkyl, aryl) through allyl metal addition, the methodology is broad in scope with regard to the choice of R group. The initially formed 1:1 diastereomeric mixture of adducts were subjected to ruthenium-catalyzed oxidation followed by acid-mediated hydrolysis of the acetate groups to obtain the hemiacetals 6a-e. Alkaline H2O2-mediated cleavage of the hemiacetals led, after esterification with diazomethane, to a chromatographically separable diastereomeric mixture of 7 and 8 in high overall yield (54-68%).

  报告了一种简短而高效的路线，可以从容易获得的同烯丙醇醋酸酯与1,2,3,4-四氯-5,5-二甲氧基环戊烯-1,3-二烯之间的Diels-Alder加合物出发，合成δ-内酯融合的环戊烷族化合物。由于同烯丙醇是通过烯丙金属的加成反应从相应的醛RCHO（R = 烷基、芳基）中衍生而来，因此该方法在R基团的选择上具有广泛的适用性。最初形成的1:1的抗异构体混合物经过钌催化氧化后，进而通过酸介导的醋酸基水解获得半醚6a-e。碱性过氧化氢对半醚的裂解，在与氮甲烷酯化后，得到了可通过色谱分离的抗异构体混合物7和8，整体产率高达54-68%。
• Process for the synthesis of unsaturated alcohols
  申请人：Maughon R. Bob

  公开号：US20050080301A1

  公开（公告）日：2005-04-14

  A process of preparing an unsaturated alcohol (olefin alcohol), such as, a homo-allylic mono-alcohol or homo-allylic polyol, involving protecting a hydroxy-substituted unsaturated fatty acid or fatty acid ester, such as methyl ricinoleate, derived from a seed oil, to form a hydroxy-protected unsaturated fatty acid or fatty acid ester; homo-metathesizing or cross-metathesizing the hydroxy-protected unsaturated fatty acid or fatty acid ester to produce a product mixture containing a hydroxy-protected unsaturated metathesis product; and deprotecting the hydroxy-protected unsaturated metathesis product under conditions sufficient to prepare the unsaturated alcohol. Preferably, methyl ricinoleate is converted by cross-metathesis or homo-metathesis into the homo-allylic mono-alcohol 1-decene-4-ol or the homo-allylic polyol 9-octadecene-7,12-diol, respectively.

  一种制备不饱和醇（烯醇）的过程，例如，保护羟基取代的不饱和脂肪酸或脂肪酸酯，例如来自种子油的甲基蓖麻油酸甲酯，形成羟基保护的不饱和脂肪酸或脂肪酸酯; 同型交换或交叉交换羟基保护的不饱和脂肪酸或脂肪酸酯，以产生含有羟基保护的不饱和交换产物的产物混合物; 并在足以制备不饱和醇的条件下去除羟基保护的不饱和交换产物。优选地，通过交叉或同型交换将甲基蓖麻油酸甲酯转化为同型烯丙基单醇1-癸烯-4-醇或同型烯丙基多醇9-十八烯-7,12-二醇。
• Synthesis of 2-substituted tetrahydrofurans
  作者：N. P. Volynskii、L. I. Perepelitchenko

  DOI：10.1007/bf00486670

  日期：1988.12
• Segment-coupling Prins cyclizations
  作者：Scott D. Rychnovsky、Yueqing Hu、Bruce Ellsworth

  DOI：10.1016/s0040-4039(98)01586-x

  日期：1998.10

  A segment-coupling Prins cyclization was developed involving (1) esterification, (2) reductive acetylation and (3) Lewis acid promoted cyclization. A model for the bis-tetrahydropyran segment of phorboxazole was successful assembled using this new method. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• VOLYNSKIJ, N. P.;PEREPELITCHENKO, L. I., XIMIYA GETEROTSIKL. SOED.,(1988) N2, S. 1604-1607
  作者：VOLYNSKIJ, N. P.、PEREPELITCHENKO, L. I.

  DOI：——

  日期：——