ethyl (4E,6RS)-6-methyl-4-octenoate | 179617-49-3

• 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: ethyl (4E,6RS)-6-methyl-4-octenoate
• 英文别名: ethyl (4E)-6-methyloct-4-enoate；(E)-ethyl 6-methyl-4-octenoate；ethyl (E)-6-methyloct-4-enoate
• CAS: 179617-49-3
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: WIDBRKDALFFOQL-SOFGYWHQSA-N

物化性质

• 沸点：
  211.7±9.0 °C(Predicted)
• 密度：
  0.887±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  ethyl (4E,6RS)-6-methyl-4-octenoate 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 19.5h， 生成 (E)-7-methyl-5-nonenenitrile
  参考文献：
  名称：

  通过原酸酯克莱森重排进行辣椒素类化合物的一般和立体选择性合成

  摘要：

  辣椒素是辣椒的主要辛辣成分，它的15种类似物已得到有效合成。这种合成的sheme的关键步骤是原酸酯Claisen重排，它以高度立体选择性的方式将烯丙醇2A-C转变为（E）-链烯酸酯3A-C（）。随后的基于氰化或丙二酸酯合成的碳链在3上的延伸得到（E）-链烯酸8，将其转化为相应的酰氯，然后与香草醛偶联以得到辣椒素。还对这些辣椒素进行了HPLC和CE（毛细管电泳）分析。

  DOI：

  10.1016/0040-4020(96)00414-0
• 作为产物：
  描述：

  diethyl [(2E)-3-chloroprop-2-en-1-yl]propanedioate 在 iron(III)-acetylacetonate 、 水 、 sodium chloride 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 二甲基亚砜 为溶剂， 反应 16.58h， 生成 ethyl (4E,6RS)-6-methyl-4-octenoate
  参考文献：
  名称：

  A new approach to the synthesis of ethyl (4E)-alkenoates

  摘要：

  A new approach to the preparation of ethyl (4E)-alkenoates was developed on the basis of Fe-catalyzed cross-coupling of ethyl (4E)-5-chloropent-4-enoate with the Grignard reagents. The starting ethyl (4E)-5-chloropent-4-enoate was obtained by alkylation of malonic ester of (E)-1,3-dichloropropene followed by decarbethoxylation.

  DOI：

  10.1134/s1070363213110078

文献信息

• Absolute configuration of main chain of AAL-toxins.
  作者：Hideaki Oikawa、Isamu Matsuda、Takashi Kagawa、Akitami Ichihara、Keisuke Kohmoto

  DOI：10.1016/s0040-4020(01)89343-1

  日期：1994.1

  AAL-toxins TA(1) 1 and TA(2) 2, host-specific toxins produced by Alternaria alternata, were degraded to 2-methylbutanol, 3-methylnonan-1,9-diol and N-protected 4-aminobutan-1-3-diol, which were further converted to (R)-MTPA esters. These esters were correlated with synthesis samples by comparison of their 500 MHz H-1-NMR spectra. The remaining stereocenters were determined by the comparison of H-1-NMR spectra of 6a and 7 derived from 1 and 2 with those of synthetic model compounds. These data conclude that AAL-toxins possess 2S, 4S, 5R, 11S, 13S, 14R and 15R configurations.
• Fe-catalyzed synthesis of (4Z)-alkenoates
  作者：R. N. Shakhmaev、A. Sh. Sunagatullina、V. V. Zorin

  DOI：10.1134/s1070363217030306

  日期：2017.3

  A new approach to stereoselective synthesis of (4Z)-alkenoates has been developed based on Fecatalyzed cross-coupling of ethyl (4Z)-5-chloropent-4-enoate with the Grignard reagents.
• A general and stereoselective synthesis of the capsaicinoids via the orthoester Claisen rearrangement
  作者：Harumi Kaga、Kouhei Goto、Tomiki Takahashi、Masao Hino、Takashi Tokuhashi、Kazuhiko Orito

  DOI：10.1016/0040-4020(96)00414-0

  日期：1996.6

  pungent principle of hot pepper, and its 15 analogs have been efficiently synthesized. The key step of this synthetic sheme is the orthoester Claisen rearrangement, which transformed allylic alcohols 2A-C to (E)-alkenoates 3A-C () in a highly stereoselective manner. The subsequent carbon chain elongations on 3 based on the cyanation or the malonic acid ester synthesis afforded (E)-alkenoic acids 8, which

  辣椒素是辣椒的主要辛辣成分，它的15种类似物已得到有效合成。这种合成的sheme的关键步骤是原酸酯Claisen重排，它以高度立体选择性的方式将烯丙醇2A-C转变为（E）-链烯酸酯3A-C（）。随后的基于氰化或丙二酸酯合成的碳链在3上的延伸得到（E）-链烯酸8，将其转化为相应的酰氯，然后与香草醛偶联以得到辣椒素。还对这些辣椒素进行了HPLC和CE（毛细管电泳）分析。
• A new approach to the synthesis of ethyl (4E)-alkenoates
  作者：R. N. Shakhmaev、A. Sh. Sunagatullina、V. V. Zorin

  DOI：10.1134/s1070363213110078

  日期：2013.11

  A new approach to the preparation of ethyl (4E)-alkenoates was developed on the basis of Fe-catalyzed cross-coupling of ethyl (4E)-5-chloropent-4-enoate with the Grignard reagents. The starting ethyl (4E)-5-chloropent-4-enoate was obtained by alkylation of malonic ester of (E)-1,3-dichloropropene followed by decarbethoxylation.