diethyl 2-butyl-2-(2-iodoallyl)malonate | 1262883-75-9

• 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: diethyl 2-butyl-2-(2-iodoallyl)malonate
• CAS: 1262883-75-9
• 化学式: C₁₄H₂₃IO₄
• 分子量: 382.239
• InChiKey: IHNCTAAJBCBZCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  19.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-butyl-2-prop-2-ynylmalonic acid diethyl ester 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 氢碘酸 作用下， 以 水 、 甲苯 为溶剂， 反应 17.0h， 生成 、 diethyl 2-butyl-2-(2-iodoallyl)malonate
  参考文献：
  名称：

  Iridium-catalyzed hydroiodination of functionalized alkynes

  摘要：

  The efficiency of an Ir(I)/HI system has been studied. The association of hydroiodic acid with iridium has been tested in the catalytic hydroiodination of alkynes. The use of [Ir(cod)Cl](2) dimer led to clean hydroiodination reactions and afforded the corresponding vinyliodides as a mixture of derivatives, where the Markovnikov type adduct was found to be the major product (80/20 to 93/7 ratio), in good yields. The mechanism was investigated and two main pathways seemed to be involved, one based on an initial oxidative addition of HI to the Ir(I) complex and the other one based on a pi-activation of the alkyne moiety. The corresponding vinyliodides were engaged in Pd-catalyzed cross-coupling (Sonogashira and Suzuki-Miyaura) reactions under organoaqueuous conditions. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.10.052