bromo-propyl-malonic acid diethyl ester | 29237-79-4

• 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: bromo-propyl-malonic acid diethyl ester
• CAS: 29237-79-4
• 化学式: C₁₀H₁₇BrO₄
• 分子量: 281.147
• InChiKey: AZCWNVXXHATZBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  bromo-propyl-malonic acid diethyl ester 、 苯乙炔 在 五甲基二乙烯三胺 、 copper(I) bromide 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以78%的产率得到
  参考文献：
  名称：

  Copper-Catalyzed trans-Carbohalogenation of Terminal Alkynes with Functionalized Tertiary Alkyl Halides

  摘要：

  A highly trans-selective Cu-catalyzed carbohalogenation including carbobromination, carboiodination, and carbochlorination of terminal alkynes with activated tertiary alkyl halides has been realized, providing quaternary-carbon-containing alkenyl halides in good yields with excellent regio- and stereoselectivity. Meanwhile, an unprecedented alkyne trans-carboalkynylation process has been achieved via the tandem trans-carbohalogenation/Sonogashira coupling reaction, which furnishes highly functionalized 1,3-enynes in a single chemical transformation.

  DOI：

  10.1021/acs.orglett.5b00546

文献信息

• Nickel-Catalyzed Remote Arylation of Alkenyl Aldehydes Initiated by Radical Alkylation with Tertiary α-Carbonyl Alkyl Bromides
  作者：Weiwei Jin、Yulu Zhou、Ying Zhao、Qianqian Ma、Lichun Kong、Gangguo Zhu

  DOI：10.1021/acs.orglett.8b00221

  日期：2018.3.2

  A novel nickel-catalyzed remote arylation of alkenyl aldehydes triggered by radical alkylation with tertiary α-carbonyl alkyl bromides is described, thus producing a quaternary carbon center containing ketones in promising yields with broad functional group compatibility. Preliminary mechanistic studies suggest that the combination of a 1,n-HAT (n = 5 or 6) from alkyl radicals to aldehyde C–H bonds

  描述了由叔α-羰基烷基溴的自由基烷基化引发的烯基醛的新型镍催化的远程芳基化，从而以具有希望的产率与广泛的官能团相容性产生了含有酮的季碳中心。初步的机理研究表明，在镍催化下，烷基中的1，n -HAT（n = 5或6）与醛C–H键的结合可能是导致此反应的原因。
• Photo/N-Heterocyclic Carbene Co-catalyzed Ring Opening and γ-Alkylation of Cyclopropane Enal
  作者：Lei Dai、Song Ye

  DOI：10.1021/acs.orglett.9b04533

  日期：2020.2.7

  An unprecedented photo/NHC-co-catalyzed ring-opening C-C bond cleavage of cyclopropane enal and the following γ-alkylation with a halogenated compound via radicals were established, affording the corresponding γ-alkylated α,β-unsaturated esters in moderate to good yields.

  建立了空前的光/ NHC共催化的环丙烷烯的开环CC键裂解和随后的通过自由基与卤代化合物的γ-烷基化反应，从而以中等至良好的收率提供了相应的γ-烷基化的α，β-不饱和酯。
• Gilbert,J.; Gault,H., Bulletin de la Societe Chimique de France, 1962, p. 1180 - 1184
  作者：Gilbert,J.、Gault,H.

  DOI：——

  日期：——