(2E)-methyl-2-methyldecenoate | 115549-43-4

• 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: (2E)-methyl-2-methyldecenoate
• 英文别名: methyl (E)-2-methyldec-2-enoate；methyl 2-methylpent-2-enoate；methyl 2-methyldec-2-enoate
• CAS: 115549-43-4
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: RTUJVXNYXNSXGB-ZHACJKMWSA-N

物化性质

• 沸点：
  254.1±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)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  8
• 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：

  (2E)-methyl-2-methyldecenoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (E)-2-methyl-2-decenoic acid
  参考文献：
  名称：

  A facile one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids from unactivated Baylis–Hillman adducts and a simple access to some important insect pheromones

  摘要：

  An efficient one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids has been accomplished by treatment of unactivated Baylis-Hillman adducts, 3-hydroxy-2-methylencalkanoates, with Al-NiCl2-6H(2)O in methanol at room temperature followed by hydrolysis. The method has been applied to the synthesis of three important insect pheromones, (4S,2E)-2,4-dimethyl-2-hexenoic acid, (+)-(S)-manicone and (+)-(S)-normanicone. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.014
• 作为产物：
  描述：

  methyl 3-hydroxy-2-methylenedecanoate 以 甲醇 为溶剂， 反应 2.0h， 生成 (2E)-methyl-2-methyldecenoate
  参考文献：
  名称：

  A facile one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids from unactivated Baylis–Hillman adducts and a simple access to some important insect pheromones

  摘要：

  An efficient one-pot stereoselective synthesis of trisubstituted (E)-2-methylalk-2-enoic acids has been accomplished by treatment of unactivated Baylis-Hillman adducts, 3-hydroxy-2-methylencalkanoates, with Al-NiCl2-6H(2)O in methanol at room temperature followed by hydrolysis. The method has been applied to the synthesis of three important insect pheromones, (4S,2E)-2,4-dimethyl-2-hexenoic acid, (+)-(S)-manicone and (+)-(S)-normanicone. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.014

文献信息

• Volatile Methyl Esters of Medium Chain Length from the Bacterium Chitinophaga Fx7914
  作者：Thorben Nawrath、Klaus Gerth、Rolf Müller、Stefan Schulz

  DOI：10.1002/cbdv.201000190

  日期：——

  The analysis of the volatiles released by the novel bacterial isolate Chitinophaga Fx7914 revealed the presence of ca. 200 compounds including different methyl esters. These esters comprise monomethyl- and dimethyl-branched, saturated, and unsaturated fatty acid methyl esters that have not been described as bacterial volatiles before. More than 30 esters of medium C-chain length were identified, which

  对新型细菌分离物Chitinophaga Fx7914释放的挥发物的分析表明存在ca。200种化合物，包括不同的甲酯。这些酯包含以前从未被描述为细菌挥发物的单甲基和二甲基支化的，饱和和不饱和的脂肪酸甲酯。鉴定出30多种中等C链长度的酯，它们属于5个主要类别，即（S）-2-甲基链烷酸甲酯（A类），（S）-2甲基，（ω-1）-二甲基链烷酸甲酯（B类） ），2，（ω-2）-二甲基链烷酸甲酯（C类），（E）-2-甲基烷-2-烯酸甲酯（D类）和甲基（E）-2，（ω-1）-二甲基烷- 2-烯酸酯（E类）。通过GC / MS分析和目标化合物的合成验证了化合物的结构，即目标化合物为（S）-2-甲基辛酸甲酯（28），（S）-2,7-二甲基辛酸甲酯（（S）-43），2,6-二甲基辛酸甲酯（49），（E）-2-甲基壬-2-烯酸甲酯（20a）和（E）-2,7-二甲基辛-2-烯酸甲酯（41a）。此外，如通过使用手性相的GC
• Simple, Chemoselective, Catalytic Olefin Isomerization
  作者：Steven W. M. Crossley、Francis Barabé、Ryan A. Shenvi

  DOI：10.1021/ja5105602

  日期：2014.12.3

  Catalytic amounts of Co(SaltBu,tBu)Cl and organosilane irreversibly isomerize terminal alkenes by one position. The same catalysts effect cycloisomerization of dienes and retrocycloisomerization of strained rings. Strong Lewis bases like amines and imidazoles, and labile functionalities like epoxides, are tolerated.

  催化量的 Co(SaltBu,tBu)Cl 和有机硅烷不可逆地使末端烯烃异构化一个位置。相同的催化剂影响二烯的环异构化和应变环的逆环异构化。可以耐受强路易斯碱（如胺和咪唑）和不稳定的官能团（如环氧化物）。
• A Facile Zn-mediated Stereoselective Synthesis of (<i>E</i>)- and (<i>Z</i>)-Trisubstituted Alkenes from Baylis–Hillman Adducts in Water and Its Application
  作者：Biswanath Das、Nikhil Chowdhury、Joydeep Banerjee、Anjoy Majhi、Gurram Mahender

  DOI：10.1246/cl.2006.358

  日期：2006.4

  A simple and efficient stereoselective synthesis of (E)- and (Z)-trisubstituted alkenes has been accomplished by treatment of the acetyl derivatives of the Baylis-Hillman adducts with Zn in saturated aq. NH 4 Cl solution under reflux. The method has been utilized for the preparation of the two chiral insect pheromones, dominicalure-I and dominicalure-II, of the lesser grain borer Rhyzopertha dominica

  通过用饱和水溶液中的 Zn 处理 Baylis-Hillman 加合物的乙酰衍生物，已经完成了 (E)- 和 (Z)- 三取代烯烃的简单有效的立体选择性合成。NH 4 Cl 溶液回流。该方法已用于制备小螟Rhyzopertha dominica (F) 的两种手性昆虫信息素 dominicalure-I 和 dominicalure-II。
• A stereoselective synthesis of Z)-α,β-disubstituted acrylates
  作者：Masayuki Shimagaki、Manabu Shiokawa、Kazunori Sugai、Tomoko Teranaka、Tadashi Nakata、Takeshi Oishi

  DOI：10.1016/s0040-4039(00)80176-8

  日期：——

  A new route for (Z)-α,β-disubstituted acrylate is described which is made up of 1) stereoselective reduction of ketones 3 and 2) conversion of the resulting syn- into (Z)-.

  描述了一种用于（Z）-α，β-二取代丙烯酸酯的新路线，该路线由1）酮的立体选择性还原3和2）将所得syn-转化为（Z）-组成。
• Direct synthesis of Z-unsaturated esters. A useful modification of the horner-emmons olefination.
  作者：W.Clark Still、Cesare Gennari

  DOI：10.1016/s0040-4039(00)85909-2

  日期：1983.1