non-2c-enoic acid ethyl ester | 72284-17-4

• 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: non-2c-enoic acid ethyl ester
• 英文别名: Non-2c-ensaeure-aethylester；Ethyl (E)-2-nonenoate；ethyl (Z)-non-2-enoate
• CAS: 72284-17-4
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: ZCSDUGXKKBIICL-KTKRTIGZSA-N

物化性质

• 沸点：
  235.7±9.0 °C(Predicted)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  8
• 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：

  non-2c-enoic acid ethyl ester 生成 1-bromo-oct-1-ene
  参考文献：
  名称：

  Sliwa,H.; Maitte,P., Bulletin de la Societe Chimique de France, 1962, p. 369 - 374

  摘要：

  DOI：
• 作为产物：
  描述：

  2-壬炔酸乙酯 在 Lindlar's catalyst 作用下， 生成 non-2c-enoic acid ethyl ester
  参考文献：
  名称：

  Sliwa,H.; Maitte,P., Bulletin de la Societe Chimique de France, 1962, p. 369 - 374

  摘要：

  DOI：

文献信息

• Practical Synthesis of (E)-α,β-Unsaturated Esters from Aldehydes
  作者：Benjamin List、Arno Doehring、Maria T. Hechavarria Fonseca、Kathrin Wobser、Hendrik van Thienen、Ramon Rios Torres、Pedro Llamas Galilea

  DOI：10.1002/adsc.200505196

  日期：2005.10

  Based on a modification of the Doebner–Knoevenagel reaction, a practical and highly efficient synthesis of α,β-unsaturated esters with excellent regio- and stereoselectivity was developed. The reactions are catalyzed by 4-dimethylaminopyridine in DMF at room temperature or below. Both aliphatic and aromatic aldehydes can readily be used in the process.

  基于对Doebner-Knoevenagel反应的改进，开发了一种实用且高效的合成方法，该方法具有极佳的区域选择性和立体选择性，可合成α，β-不饱和酯。在室温或更低温度下，在DMF中由4-二甲基氨基吡啶催化反应。脂族和芳族醛都可以容易地用于该方法中。
• 1,3-dimethyl 2-oxo 1,3,2-diazaphospholidine precursor of (Z) α,β-unsaturated esters.
  作者：Carl Patois、Philippe Savignac

  DOI：10.1016/s0040-4039(00)79655-9

  日期：1991.3

  alpha,beta-Unsaturated esters of (Z) geometry are selectively obtained from cyclic phosphonocarboxylates derived from N,N'-dimethylethylenediamine.
• A Highly Stereoselective TMSOTf-Mediated Catalytic Carbocupration of Alkynoates
  作者：Amanda J. Mueller、Michael P. Jennings

  DOI：10.1021/ol702546w

  日期：2007.12.1

  The TMSOTf-mediated catalytic carbocupration of ynoates has been investigated. It has been shown that catalyst loadings as low as 5 mol % readily allow for high yields and diastereoselectivities for a series of aromatic Grignard reagents. In addition, we have been successful in vicinally functionalizing 1a via initial TMSOTf-mediated catalytic carbocupration followed by a secondary electrophilic capture of the TMS allenoate intermediate.
• ——
  作者：Derek C. Martyn、Deborah A. Hoult、Andrew D. Abell

  DOI：10.1071/ch01093

  日期：——

  A systematic study on the Horner-Wadsworth-Emmons (HWE) reaction has shown that ethyl diphenylphosphonoacetate and methyl diphenylphosphonoacetate give a high excess of (Z)-alkenes. These reaction conditions were then used to prepare (Z)-ethyl-5-phenylpent-2-enoate, the corresponding (E)-isomer being prepared by standard Wittig chemistry. Reduction of each allylic ester, with diisobutylaluminium hydride (DIBAL), gave the allylic alcohols (15) and (19), respectively. Epoxidation of (15) and (19), under Sharpless conditions, gave separate samples of all four stereoisomers of 2,3-epoxy-5-phenylpentan-1-ol. Esterification of each isomer with Cbz-valine, under Mitsunobu conditions, provided (9)-(12) which were assayed against HIV protease. The cis series (9)-(10) proved to be significantly more potent than the trans (11)-(12) and, within each of these series, the isomers derived from L-diisopropyltartrate [(9) and (11)] were the most active.
• Dhavale, Dilip D.; Sindkhedkar, Milind D.; Mali, Raghao S., Journal of Chemical Research - Part S, 1995, # 10, p. 414 - 415
  作者：Dhavale, Dilip D.、Sindkhedkar, Milind D.、Mali, Raghao S.

  DOI：——

  日期：——