5-dodecynal | 1025737-54-5

• 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: 5-dodecynal
• 英文别名: Dodec-5-ynal
• CAS: 1025737-54-5
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: OTKZSAMKARJRCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  5-dodecynal 在 titanium(IV) isopropylate 、 盐酸 、 正丁基锂 、 二异丙氧基二氯化钛 、 异丙基氯化镁 、 苯甲醛 作用下， 以 乙醚 为溶剂， 生成 1-<(E)-heptylidene>-2-methylenecyclopentane
  参考文献：
  名称：

  Aldehyde Addition and Copper-Mediated Allylation of Bicyclic Alkoxytitanacyclopentenes and -Pentadienes:  New Selectivities and an Unusual Reaction

  摘要：

  Bicyclic titanacyclopentenes generated in situ from 1,6-enynes and (eta(2)-propene)Ti(O-i-Pr)(2) (1) reacted with aldehydes at their alkenyl-titanium bond in the absence or presence of Ti(O-i-Pr)(n)Cl(4-n) (n = 2 or 3) to give allyl alcohols such as 5-7 as a nearly single stereoisomer in good yields. Upon workup with DCl/D(2)O or iodine, deuterio and iodo derivatives, 8 and 9, were obtained. Bicyclic titanacyclopentadienes prepared analogously from 1,6- or 1,7-diynes and 1 also reacted with aldehydes in the presence of an additional equivalent of Ti(O-i-Pr)(2)Cl(2) to afford 1,2-dialkylidenecyclopentanes pr -cyclohexanes having an alcohol moiety in their side chain in good yields. In place of the simple hydrolysis, deuteriolysis or iodinolysis gave the corresponding derivatives such as 21 or 22. Treatment of 1,6-enyne 10 with 1 in the standard way and then with a slight excess of i-PrMgCl at -50 degrees C generated a new titanium species that, upon reaction with aldehydes, afforded unexpected adducts 34 and 41-45 virtually as a single isomer. Copper-mediated allylation of dialkoxytitanacyclopentene such as 3 with allyl bromide proceeded at their vinyl-titanium bond to give 48 and 50. Likewise, dialkoxytitanacyclopentadiene prepared from 29 and 1 underwent the regioselective copper-mediated mono-allylation to give a 9:1 mixture of 53 and 54. Upon workup with deuteriochloric acid, the corresponding deuterated product was obtained with a high degree of deuterium incorporation.

  DOI：

  10.1021/ja982501e
• 作为产物：
  描述：

  十二碳-5-炔-1-醇 在 N-甲基吗啉 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.5h， 以50%的产率得到5-dodecynal
  参考文献：
  名称：

  Synthesis and Stereochemistry-Activity Relationship of small Bacteriocin, an Autoinducer of the Symbiotic Nitrogen-Fixing Bacterium Rhizobium leguminosarum

  摘要：

  The four stereoisomers of small bacteriocin, an autoinducer of the symbiotic nitrogen-fixing bacterium Rhizobium leguminosarum, were synthesized via a versatile methodology for 3'-hydroxyacyl homoserine lactones based on the Nagao asymmetric aldol reaction. The synthetic isomers were much less effective at inhibiting the growth of R. leguminosarum RBL5523 than the natural isomer, showing the importance of stereochemistry for activity.

  DOI：

  10.1021/ol8005198