ethyl (Z)-4-methylhex-2-enoate | 169735-64-2

• 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 (Z)-4-methylhex-2-enoate
• CAS: 169735-64-2
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: KSUBDACSDSKWPF-SREVYHEPSA-N

物化性质

• 沸点：
  188.8±9.0 °C(Predicted)
• 密度：
  0.894±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙炔酸乙酯 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.83h， 生成 ethyl (Z)-4-methylhex-2-enoate
  参考文献：
  名称：

  Diastereoselective synthesis of α,β-unsaturated systems

  摘要：

  Functionalized Z-vinylic tellurides were used in substitution reactions with lower order cyanocuprates leading to alpha, beta-unsaturated ketones and esters in good yields. In the case of acyclic tellurides, the product was obtained in high diastereoselectivity. The control of the stereoselectivity was achieved by simple change of the reaction temperature. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.025

文献信息

• Practical synthesis of Z-unsaturated esters by using a new Horner-Emmons reagent, ethyl diphenylphosphonoacetate
  作者：Kaori Ando

  DOI：10.1016/0040-4039(95)00726-s

  日期：1995.6

  A new Horner-Emmons reagent, ethyl diphenylphosphonoacetate 1 was prepared from triethyl phosphonoacetate, PCl5, and phenol in 60% overall yield. Horner-Emmons reactions of 1 with aldehydes in the presence of Triton® B or NaH in THF gave the Z-unsaturated esters in 89–93% selectivity in almost quantitative yields. Furthermore, 1 showed up to 99% Z-selectivity under Still's condition (KHMDS/18-crown-6)

  由膦酸三乙酯，PCl 5和苯酚制备了一种新的Horner-Emmons试剂二苯基膦酸乙酯1，总收率为60％。的霍纳-埃蒙斯反应1与曲通的存在醛®，在THF乙或NaH得到Ž以几乎定量的产率不饱和酯在89-93％的选择性。此外，在斯蒂尔条件下（KHMDS / 18-crown-6），1表现出高达99％的Z选择性。
• Diastereoselective synthesis of α,β-unsaturated systems
  作者：Priscila Castelani、João V. Comasseto

  DOI：10.1016/j.tet.2005.01.025

  日期：2005.2

  Functionalized Z-vinylic tellurides were used in substitution reactions with lower order cyanocuprates leading to alpha, beta-unsaturated ketones and esters in good yields. In the case of acyclic tellurides, the product was obtained in high diastereoselectivity. The control of the stereoselectivity was achieved by simple change of the reaction temperature. (C) 2005 Elsevier Ltd. All rights reserved.