2,2-Dideuteriododecyl aldehyde | 129355-47-1

• 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: 2,2-Dideuteriododecyl aldehyde
• CAS: 129355-47-1
• 化学式: C₁₂H₂₄O
• 分子量: 186.306
• InChiKey: HFJRKMMYBMWEAD-ZWGOZCLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  13.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,2-Dideuteriododecyl aldehyde 在 sodium hydroxide 、 potassium permanganate 、 氯化亚砜 、 硫酸 作用下， 以 水 为溶剂， 反应 6.5h， 生成 N-2,2-Dideuteriododecanoyl-L-alanine
  参考文献：
  名称：

  Investigation into the mechanism for generation of the helical axis in cholesteric lyotropic liquid crystals

  摘要：

  The molecular based process responsible for the generation of the helical axis in the cholesteric mesophase of potassium N-dodecanoyl-L-alaninate, decanol, electrolyte, and water has been investigated. The headgroup dipolar couplings have been correlated with deuterium quadruple splittings from the aliphatic chain as a function of amphiphile concentration. The results show that the change in the pitch of the helical axis with concentration is reflected by a change in preferred conformation of the amphiphile. This change in conformation is centered about the amide bonds where the aliphatic chain is joined to the alaninate headgroups. The effect presumably results from destabilization of the normally preferred rotamer in favor of others and will have its source in selective interactions between the chiral centers of adjacent amphiphiles. Studies similar to those discussed show that the variation in pitch caused by temperature changes is not correlated with similar selective changes in headgroup orientation.

  DOI：

  10.1021/j100188a058
• 作为产物：
  描述：

  十二醛 在 吡啶 、 重水 作用下， 反应 16.0h， 生成 2,2-Dideuteriododecyl aldehyde
  参考文献：
  名称：

  Investigation into the mechanism for generation of the helical axis in cholesteric lyotropic liquid crystals

  摘要：

  The molecular based process responsible for the generation of the helical axis in the cholesteric mesophase of potassium N-dodecanoyl-L-alaninate, decanol, electrolyte, and water has been investigated. The headgroup dipolar couplings have been correlated with deuterium quadruple splittings from the aliphatic chain as a function of amphiphile concentration. The results show that the change in the pitch of the helical axis with concentration is reflected by a change in preferred conformation of the amphiphile. This change in conformation is centered about the amide bonds where the aliphatic chain is joined to the alaninate headgroups. The effect presumably results from destabilization of the normally preferred rotamer in favor of others and will have its source in selective interactions between the chiral centers of adjacent amphiphiles. Studies similar to those discussed show that the variation in pitch caused by temperature changes is not correlated with similar selective changes in headgroup orientation.

  DOI：

  10.1021/j100188a058

文献信息

• Ruthenium-Catalyzed Hydration of 1-Alkynes to Give Aldehydes:  Insight into <i>a</i><i>nti</i>-Markovnikov Regiochemistry
  作者：Makoto Tokunaga、Toshiaki Suzuki、Nobuaki Koga、Tomoaki Fukushima、Akira Horiuchi、Yasuo Wakatsuki

  DOI：10.1021/ja0119292

  日期：2001.12.1

  acetylene C [bond] H or tautomerization of eta(2)-alkyne to a vinylidene complex, but rather protonation of the coordinated 1-alkyne at the substituted carbon to form a metal-vinyl intermediate. This cationic intermediate then isomerizes to Ru(IV)-hydride-vinylidene via alpha-hydride migration of the vinyl group to the metal center, followed by attack of the vinylidene alpha-carbon by OH(-) to give the metal-hydride-acyl

  通过分离有机和有机金属副产物、氘标记实验和 DFT 计算，研究了 1-炔烃通过水合选择性转化为醛的机理。1-炔烃的 D 标记的炔氢仅存在于所得醛的甲酰基中。反应后，确认存在金属配位的 CO。所有实验结果都强烈表明，金属-酰基中间体与原始炔氢也作为氢化物结合到金属中心，下一步是通过还原消除来释放醛。理论分析表明，催化循环的第一步不是乙炔 C [键] H 的氧化加成或 eta(2)-炔烃与亚乙烯基络合物的互变异构化，而是在取代碳上配位的 1-炔烃质子化以形成金属-乙烯基中间体。然后，该阳离子中间体异构化为 Ru(IV)-氢化物-亚乙烯基，通过乙烯基向金属中心的 α-氢化物迁移，然后用 OH(-) 攻击亚乙烯基 α-碳，得到金属氢化物-酰基中间的。