2-hexadecenal | 3163-37-9

• 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: 2-hexadecenal
• 英文别名: hexadec-2-enal
• CAS: 3163-37-9
• 化学式: C₁₆H₃₀O
• 分子量: 238.414
• InChiKey: KLJFYXOVGVXZKT-UHFFFAOYSA-N

物化性质

• 熔点：
  34 °C
• 沸点：
  332.6±11.0 °C(Predicted)
• 密度：
  0.840±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2-hexadecenal 在 臭氧 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 肉豆蔻醛
  参考文献：
  名称：

  Oxidation of Plasmalogen, Low-Density Lipoprotein and RAW 264.7 Cells by Photoactivatable Atomic Oxygen Precursors

  摘要：

  AbstractThe oxidation of lipids by endogenous or environmental reactive oxygen species (ROS) generates a myriad of different lipid oxidation products that have important roles in disease pathology. The lipid oxidation products obtained in these reactions are dependent upon the identity of the reacting ROS. The photoinduced deoxygenation of various aromatic heterocyclic oxides has been suggested to generate ground state atomic oxygen (O[3P]) as an oxidant; however, very little is known about reactions between lipids and O(3P). To identify lipid oxidation products arising from the reaction of lipids with O(3P), photoactivatable precursors of O(3P) were irradiated in the presence of lysoplasmenylcholine, low‐density lipoprotein and RAW 264.7 cells under aerobic and anaerobic conditions. Four different aldehyde products consistent with the oxidation of plasmalogens were observed. The four aldehydes were: tetradecanal, pentadecanal, 2‐hexadecenal and hexadecanal. Depending upon the conditions, either pentadecanal or 2‐hexadecenal was the major product. Increased amounts of the aldehyde products were observed in aerobic conditions.

  DOI：

  10.1111/php.12201
• 作为产物：
  描述：

  2-hexadecen-1-ol 在 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.0h， 以90%的产率得到2-hexadecenal
  参考文献：
  名称：

  (+)-Aculeatin D 和 (+)-6-epi-Aculeatin D 的全合成

  摘要：

  螺缩酮天然产物(+)-aculeatin D和非天然(+)-6-epi-aculeatin D的立体选择性全合成已经完成。仲烯丙醇和苯基碘 (III) 双（三氟乙酸酯）（PIFA）介导的氧化螺环化的 Sharpless 动力学拆分被用作该合成的关键步骤。

  DOI：

  10.1055/s-0029-1218546

文献信息

• A Simple and Inexpensive Synthesis of 2-Alkenals
  作者：Yu-Hui Chang、Biing-Jiun Uang、Chung-May Wu、Tung-Hsi Yu

  DOI：10.1055/s-1990-27086

  日期：——

  A simple and inexpensive method for the C2 homologation of aldehydes and ketone to 2-alkenals consists of the reaction with allylmagnesium bromide, O-acylation of the resultant 1-alken-4-ol, and ozonolysis.

  一种简单且廉价的醛和酮C2同源化为2-烯醛的方法包括与溴代烯丙基镁反应、对所得的1-烯-4-醇进行O-酰化，以及臭氧化反应。
• Process for the preparation of sphingosine derivatives
  申请人：Solco Basel AG

  公开号：US04952683A1

  公开（公告）日：1990-08-28

  New compounds of the formula (I)-D and (I)-L as shown in the sheet of formulae are described, for example D- and L-erythro-1-(.beta.-D-glycopyranosyloxy)-3-hydroxy-2-palmitoylamino-4-tran s-octadecene, which exert actions promoting wound healing and cell and tissue regeneration, and can be used therapeutically for the treatment of wounds of any cause. They are prepared in good yield and in a stereochemically homogeneous form from ceramides of the formula (II)-D and/or (II)-L. The process comprises the protection of the 1-hydroxyl group, esterification of the 3-hydroxyl group, elimination of the 1-hydroxyl protective group, reaction with the trifluoroacetimidate or trichloroacetimidate of a 2,3,4,6-tetraacylated D-glucose and elimination of the O-acyl groups. When a D,L-ceramide (II) is used, the esterification of the 3-hydroxyl group is carried out by an optically active acid followed by separation into the diastereomers, or separation into the diastereomers is carried out after the reaction with the D-glucose derivative.

  本文描述了一些新的化合物，它们的化学式为（I）-D和（I）-L，例如D-和L-erythro-1-（.beta.-D-葡萄糖苷氧基）-3-羟基-2-棕榈酰胺基-4-反式-十八烷，这些化合物具有促进伤口愈合和细胞组织再生的作用，并可用于治疗任何原因引起的伤口。它们可以从化学式（II）-D和/或（II）-L的鞘氨醇中高产高纯度地制备而成。该过程包括保护1-羟基基团，酯化3-羟基基团，去除1-羟基保护基团，与2,3,4,6-四酰基-D-葡萄糖的三氟乙酸酰亚胺盐或三氯乙酸酰亚胺盐反应，去除O-酰基团。当使用D，L-鞘氨醇（II）时，通过手性酸酯化3-羟基基团，然后将其分离成对映异构体，或在与D-葡萄糖衍生物反应后将其分离成对映异构体。
• Total Synthesis of (+)-Aculeatin D and (+)-6-epi-Aculeatin D
  作者：J. Yadav、K. Rao、K. Ravindar、B. Reddy

  DOI：10.1055/s-0029-1218546

  日期：2010.1

  synthesis of spiroketal natural product (+)-aculeatin D and unnatural (+)-6-epi-aculeatin D has been accomplished. Sharpless kinetic resolution of secondary allylic alcohol and phenyliodine(III) bis(trifluoroacetate) (PIFA)-mediated oxidative spirocyclization were used as key steps in this synthesis.

  螺缩酮天然产物(+)-aculeatin D和非天然(+)-6-epi-aculeatin D的立体选择性全合成已经完成。仲烯丙醇和苯基碘 (III) 双（三氟乙酸酯）（PIFA）介导的氧化螺环化的 Sharpless 动力学拆分被用作该合成的关键步骤。
• Oxidation of Plasmalogen, Low-Density Lipoprotein and RAW 264.7 Cells by Photoactivatable Atomic Oxygen Precursors
  作者：Max T. Bourdillon、Benjamin A. Ford、Ashley T. Knulty、Colleen N. Gray、Miao Zhang、David A. Ford、Ryan D. McCulla

  DOI：10.1111/php.12201

  日期：2014.3

  AbstractThe oxidation of lipids by endogenous or environmental reactive oxygen species (ROS) generates a myriad of different lipid oxidation products that have important roles in disease pathology. The lipid oxidation products obtained in these reactions are dependent upon the identity of the reacting ROS. The photoinduced deoxygenation of various aromatic heterocyclic oxides has been suggested to generate ground state atomic oxygen (O[3P]) as an oxidant; however, very little is known about reactions between lipids and O(3P). To identify lipid oxidation products arising from the reaction of lipids with O(3P), photoactivatable precursors of O(3P) were irradiated in the presence of lysoplasmenylcholine, low‐density lipoprotein and RAW 264.7 cells under aerobic and anaerobic conditions. Four different aldehyde products consistent with the oxidation of plasmalogens were observed. The four aldehydes were: tetradecanal, pentadecanal, 2‐hexadecenal and hexadecanal. Depending upon the conditions, either pentadecanal or 2‐hexadecenal was the major product. Increased amounts of the aldehyde products were observed in aerobic conditions.