5-iodo-1-prop-2-enoxypent-2-yne | 149759-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-iodo-1-prop-2-enoxypent-2-yne
• CAS: 149759-80-8
• 化学式: C₈H₁₁IO
• 分子量: 250.079
• InChiKey: MLNDMCCCQDARKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  lithium (Me(O(1-))C)pentacarbonylchromium 、 5-iodo-1-prop-2-enoxypent-2-yne 在 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 pentacarbonyl{1-{{5-(2-propenyloxy)-3-pentynyl}oxy}ethylidene}chromium
  参考文献：
  名称：

  酰基金属化物与烷基碘化物烷基化制备费希尔卡宾络合物

  摘要：

  Neutral Fischer carbene complexes bearing alkoxy groups as the donor substituents on the carbene carbon atom have been synthesized by direct alkylation of the lithium acylmetalates (formed by classical addition of organolithium compounds to metal hexacarbonyl) by alkyl iodides. It was shown that the reaction proceeds under normal phase-transfer conditions (CH2-Cl2/H2O) or, preferably, in aqueous medium alone. However, in both cases the presence of a catalytic amount of a tetraalkylammonium salt (n-Bu4NBr) was required. Attractive features of this methodology are (i) the economy of using alkyl iodides in place of the usual alkylating agents (like Me3O+BF4-, magic methyl, or methyl triflate), (ii) the procedural ease of ''one-pot'' preparation of the carbene complexes, and (iii) the greater variety of alkyl moieties that can be incorporated as part of the alkoxy substituent using the more readily available alkyl iodides containing nontrivial alkyl groups. The procedure is preparatively useful for accessing chromium-containing carbenes, but yields of the analogous molybdenum- and tungsten-containing species are only less-than-or-equal-to 10%. Mechanistic considerations suggest that products are formed by competing pathways involving direct S(N)2 displacement vs electron-transfer-initiated S(RN)1 processes.

  DOI：

  10.1021/om00031a056