α-iodopropionyl chloride | 15876-96-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: α-iodopropionyl chloride
• 英文别名: 2-iodinepropionyl chloride；2-iodopropanoyl chloride；dl-α-iodo-propionyl chloride；dl-α-Jod-propionylchlorid；2-Jod-propionylchlorid
• CAS: 15876-96-7
• 化学式: C₃H₄ClIO
• 分子量: 218.422
• InChiKey: VSTOKWPWMJSOHY-UHFFFAOYSA-N

物化性质

• 沸点：
  169.3±23.0 °C(Predicted)
• 密度：
  2.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-iodopropionyl chloride 在 三乙胺 作用下， 以 四氯化碳 为溶剂， 生成
  参考文献：
  名称：

  Hertenstein, Ulrich; Huenig, Siegfried; Reichelt, Helmut, Chemische Berichte, 1982, vol. 115, # 1, p. 261 - 287

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘丙酸 在 氯化亚砜 作用下， 生成 α-iodopropionyl chloride
  参考文献：
  名称：

  Abderhalden; Guggenheim, Chemische Berichte, 1908, vol. 41, p. 2853

  摘要：

  DOI：

文献信息

• Indirect Electroreductive Cyclization of N-Allyl and N-Propargylamides Using a Nickel(II) Complex as an Electron-Transfer Catalyst: Selective Formation of Halogenated and Non-halogenated Pyrrolidinones.
  作者：Shigeko OZAKI、Hidenori MATSUSHITA、Miho EMOTO、Hidenobu OHMORI

  DOI：10.1248/cpb.43.32

  日期：——

  Nickel(II) complex-catalyzed indirect electroreduction of N-allyl and N-propargyl-α-bromoamides conducted in dimethylformamide with 2 eq of a hydrogen atom donor, diphenylphosphine, afforded the corresponding pyrrolidinones as the sole cyclized product in good yields, while that of N-allyl-α-iodoamides in acetonitrile gave the iodinated pyrrolidinones. Under both conditions the trans-C-3 : C-4 pyrrolidinones were formed predominantly.

  镍(II)复合物催化的间接电还原反应在二甲基甲酰胺中进行，使用2个等量的氢原子供体二苯基膦，N-烯丙基和N-丙炔基α-溴酰胺得到了相应的吡咯烷酮，作为唯一的环化产物，产率良好；而在乙腈中，N-烯丙基α-碘酰胺的反应则得到了碘化吡咯烷酮。在这两种条件下，转型C-3 : C-4的吡咯烷酮主要生成。
• Stereoselectivity of 6-<i>Exo</i> Cyclization of α-Carbamoyl Radicals
  作者：Liyan Song、Xinqiang Fang、Zijia Wang、Kun Liu、Chaozhong Li

  DOI：10.1021/acs.joc.6b00008

  日期：2016.3.18

  stereoselectivity in the 6-exo cyclization of α-carbamoyl radicals was investigated experimentally and theoretically. The BEt3/O2-initiated iodine-atom-transfer radical cyclization reactions of substituted N-(but-3-en-1-yl)-N-(tert-butyl)-2-iodoalkanamides were carried out, which led to the predominant formations of 3,4-cis, 4,5-trans, or 4,6-trans substituted δ-lactams. Density functional calculations at the

  实验和理论上研究了α-氨基甲酰基自由基在6 - exo环化中的立体选择性。进行了由BEt 3 / O 2引发的取代的N-（but-3-en-1-yl）-N-（叔丁基）-2-碘代烷酰胺的碘原子转移自由基环化反应，导致3,4-顺式，4,5-反式或4,6-反式取代的δ-内酰胺的主要形成。在B3LYP / 6-31G *级别的密度泛函计算表明，6- exo自由基环化通过船构构过渡态进行。此外，提供了对立体选择性的机械见解，计算结果与实验观察结果非常吻合。
• 一种基于2-卤丙酰氯合成丙烯酰吗啉的方法
  申请人：无锡海特圣大光电材料科技有限公司

  公开号：CN104628678B

  公开（公告）日：2016-06-15

  本发明公开了一种基于2-卤丙酰氯合成丙烯酰吗啉的方法，本发明提供一种基于2-卤丙酰氯与吗啉发生仲酰胺化反应生成中间产物2-卤丙酰吗啉，并在乙醇钠作用下发生消去反应合成含双键丙烯酰吗啉单体。本发明合成丙烯酰吗啉的方法，所用原料价格低廉、结构稳定，合成的中间体不含活泼基团，不易发生副反应，最终产品的收率和纯度都较高。本发明提供的合成方法工艺流程简便，具有实现工业化大规模生产的前景。
• Efficient Regio- and Stereoselective Formation of Azocan-2-ones via 8-<i>Endo</i> Cyclization of α-Carbamoyl Radicals
  作者：Xinqiang Fang、Kun Liu、Chaozhong Li

  DOI：10.1021/ja9082649

  日期：2010.2.24

  The iodine-atom-transfer 8-endo cyclization of alpha-carbamoyl radicals was investigated experimentally and theoretically. With the aid of Mg(ClO4)(2) and a bis(oxazoline) ligand, N-ethoxycarbonyl-substituted N-(pent-4-enyl)-2-iodoalkanamides underwent 8-endo cyclization leading to the formation of only the corresponding 3,5-trans-substituted azocan-2-ones in excellent yields Similarly, the BF3 center dot OEt2/H2O-promoted reactions of N-ethoxycarbonyl-N-(2-allylaryl)-2-iodoalkanamides afforded exclusively the benzazocanone products with a 3,5-cis configuration in high yields The bidentate chelation of substrate radicals not only significantly improved the efficiency of cyclization but also resulted in the change of stereochemistry of azocanone products from 3,8-trans to 3,8-cis Theoretical calculations at the UB3LYP/6-31G* level revealed that the cyclization of N-carbonyl-substituted alpha-carbamoyl radicals occurs via the E-conformational transition states without the presence of a Lewis acid. On the other hand, the cyclization proceeds via the Z-conformational transition states when the substrates form the bidentate chelation with a Lewis acid In both cases, the 8-endocyclization is always fundamentally preferred over the corresponding 7-exo cyclization The complexed radicals having the more rigid conformations also allow the better stereochemical control in the iodine-atom-abstraction step To further understand the reactivity of alpha-carbamoyl radicals, the competition between the 8-endo and 5-exo cyclization was also studied The results demonstrated that the 8-endo cyclization is of comparable rate to the corresponding 5-exo cyclization for alpha-carbamoyl radicals with fixed Z-conformational transition states As a comparison, the 8-endo mode is fundamentally preferred over the 5-exo mode in the cyclization of INIH-amide substrates because the latter requires the Z-conformational transition states, whereas the former proceeds via the more stable E-conformational transition states.
• Abderhalden; Guggenheim, Chemische Berichte, 1908, vol. 41, p. 2853
  作者：Abderhalden、Guggenheim

  DOI：——

  日期：——