heptadec-8c-enal | 56797-41-2

• 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: heptadec-8c-enal
• 英文别名: (Z)-8-heptadecenal；(Z)-heptadec-8-enal
• CAS: 56797-41-2
• 化学式: C₁₇H₃₂O
• 分子量: 252.44
• InChiKey: UZXKSNXOPFPOKK-KTKRTIGZSA-N

物化性质

• 沸点：
  347.0±21.0 °C(Predicted)
• 密度：
  0.841±0.06 g/cm3(Predicted)
• 保留指数：
  1862;1871

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  heptadec-8c-enal 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.25h， 生成 8(Z)-heptadecenoic acid
  参考文献：
  名称：

  Inhibition of Oleamide Hydrolase Catalyzed Hydrolysis of the Endogenous Sleep-Inducing Lipid cis-9-Octadecenamide

  摘要：

  Oleamide (1, cis-9-octadecenamide) is a naturally occurring brain constituent that. has been shown to accumulate and disappear under conditions of sleep deprivation and sleep recovery, respectively. Synthetic 1 has been found to induce sleep in a structurally specific manner at nanomolar quantities. Hydrolysis of 1 by an enzyme (oleamide hydrolase) present in the cell membrane rapidly degrades oleamide to oleic acid (cis-9-octadecenoic acid). Such observations suggest 1 may constitute a prototypical member of a class of fatty acid primary amide biological signaling molecules in which the diversity and selectivity of function are derived from the length of the alkane chain as well as the position, stereochemistry, and degree of unsaturation. A series of inhibitors of oleamide hydrolase were designed and prepared which were expected to derive their properties through interactions with the putative active site cysteine residue within oleamide hydrolase. This approach yielded a series of rapid, selective, and highly potent inhibitors (K-i = 13 mu M to 1 nM) which in addition to their potential therapeutic value may serve as useful tools to define the biological role of oleamide.

  DOI：

  10.1021/ja954064z
• 作为产物：
  描述：

  2-羟基油酸 在 lead(IV) acetate 作用下， 以 苯 为溶剂， 反应 0.83h， 以67%的产率得到heptadec-8c-enal
  参考文献：
  名称：

  Inhibition of Oleamide Hydrolase Catalyzed Hydrolysis of the Endogenous Sleep-Inducing Lipid cis-9-Octadecenamide

  摘要：

  Oleamide (1, cis-9-octadecenamide) is a naturally occurring brain constituent that. has been shown to accumulate and disappear under conditions of sleep deprivation and sleep recovery, respectively. Synthetic 1 has been found to induce sleep in a structurally specific manner at nanomolar quantities. Hydrolysis of 1 by an enzyme (oleamide hydrolase) present in the cell membrane rapidly degrades oleamide to oleic acid (cis-9-octadecenoic acid). Such observations suggest 1 may constitute a prototypical member of a class of fatty acid primary amide biological signaling molecules in which the diversity and selectivity of function are derived from the length of the alkane chain as well as the position, stereochemistry, and degree of unsaturation. A series of inhibitors of oleamide hydrolase were designed and prepared which were expected to derive their properties through interactions with the putative active site cysteine residue within oleamide hydrolase. This approach yielded a series of rapid, selective, and highly potent inhibitors (K-i = 13 mu M to 1 nM) which in addition to their potential therapeutic value may serve as useful tools to define the biological role of oleamide.

  DOI：

  10.1021/ja954064z

文献信息

• The degradation of carboxylic acids into aldehydes
  作者：Gábor Doleschall、Gábor Tóth

  DOI：10.1016/s0040-4020(01)83135-5

  日期：1980.1

  developed for degradation of carboxylic acid into aldehydes containing one C atom less whose key step consists in α-acetoxylation of 5-alkyl-3-methylthio-1,4-diphenyl-1,2,4-triazolium iodides by (diacetoxyiodo)benzene. The mechanism of the regioselective α-acetoxylation was studied and the diacetoxyiodate(1)anion was shown to be the actual oxidising agent. Further oxidation reactions of tetraethylammonium

  开发了一种新的方法将羧酸降解为少含一个C原子的醛，其关键步骤在于通过（）将5-烷基-3-甲硫基-1,4-二苯基-1,2,4-三唑碘化物进行α-乙酰氧基化。二乙酰氧基碘）苯。研究了区域选择性α-乙酰氧基化的机理，表明二乙酰氧基碘酸（1）阴离子是实际的氧化剂。四乙铵diacetoxyiodate（的进一步氧化反应1）进行了调查。
• A Concise and Convergent Total Synthesis of Two Novel Cytotoxic Hydroquinones, Lanneaquinol and (<i>R</i>)-2′-Hydroxylanneaquinol
  作者：Basireddy V. Subba Reddy、Bheemreddy Anusha、Ummareddy V. Subba Reddy、Jhillu S. Yadav、Cirandur Suresh Reddy

  DOI：10.1002/hlca.201300066

  日期：2013.10

  A short and efficient approach for the total synthesis of two novel cytotoxic hydroquinones, lanneaquinol (1) and (R)‐2′‐hydroxylanneaquinol (2) isolated from the organic extract of the plant Lannea welwitschii, has been developed. Enantioselective organocatalytic McMillan hydroxylation has been successfully utilized for the creation of the stereogenic center bearing the OH group of (R)‐2′‐hydroxylanneaquinol

  已开发出一种短而有效的方法，用于从植物Lannea welwitschii的有机提取物中分离出的两种新型细胞毒性氢醌（lanneaquinol（1）和（R）-2'-hydroxylanneaquinol（2））全合成。对映选择性有机催化McMillan羟基化已成功地用于创建带有（R）-2'-羟基lanneaquinol（2）羟基的立体中心。对苯二酚核心是通过环己烷-1,4-二酮与相应的醛的烷基化反应而构建的。只需改变合成策略，即可合成两种对苯二酚天然产物。
• Specificity of the enzyme system producing long chain aldehydes in the green alga, Ulva pertusa
  作者：Tadahiko Kajiwara、Hiroshi Yoshikawa、Kenji Matsui、Akikazu Hatanaka、Tetsuo Kawai

  DOI：10.1016/0031-9422(89)80021-4

  日期：1989.1

  Abstract The greater part of the enzyme activity producing long chain aldehydes (LCA) such as (8Z)-heptadecenal, (8Z,11Z)-heptadecadienal, (8Z,11Z,14Z)-heptadecatrienal was found in the 4000 g precipitate of homogenates of the green alga, Ulva pertusa. The LCA-forming activity was readily solubilized from the precipitate by addition of 0.2% Triton X-100. The solubilized LCA-forming activity showed

  摘要 在 4000 g 的匀浆沉淀物中发现了大部分酶活性产生长链醛 (LCA)，如 (8Z)-十七烯醛、(8Z,11Z)-十七碳烯醛、(8Z,11Z,14Z)-十七碳三烯醛。绿藻，Ulva pertusa。通过添加 0.2% Triton X-100，很容易从沉淀物中溶解 LCA 形成活性。溶解的 LCA 形成活性显示出最佳 pH 值范围为 8.5-9.5。α-亚麻酸是一种非常好的底物，但γ-亚麻酸是一种较差的活性底物。亚油酸是整个系列 (ω6Z,ω9Z)-二烯酸的最佳底物，其中链长从 C13 到 C20。
• Enzymatic formation of unsaturated long chain fatty aldehydes in Ulva pertusa
  作者：Tadahiko Kajiwara、Hiroshi Yoshikawa、Takahiro Saruwatari、Akikazu Hatanaka、Tetsuo Kawai、Masakazu Ishihara、Tomoyuki Tsuneya

  DOI：10.1016/0031-9422(88)80419-9

  日期：1988.1

  Abstract (Z)-8-Heptadecenal, (Z,Z)-8, 11-heptadecadienal and 8,11,14-heptadecatrienal, were produced enzymatically from oleic, linoleic and linoleni

  摘要 (Z)-8-十七烯醛、(Z,Z)-8、11-十七碳二烯醛和 8,11,14-十七碳三烯醛是由油酸、亚油酸和亚麻油经酶促产生的
• Decarboxylative oxygenation of carboxylic acids with O₂<i>via</i> a non-heme manganese catalyst
  作者：Renpeng Guan、Elliot L. Bennett、Zhiliang Huang、Jianliang Xiao

  DOI：10.1039/d1gc04603a

  日期：——

  for the decarboxylative oxygenation of carboxylic acids using a non-heme manganese catalyst under blue light irradiation with O2 as the sole oxidant. Featuring mild reaction conditions, the protocol allows readily available carboxylic acids to be converted into a wide variety of valuable aldehydes, ketones and amides. Mechanistic studies indicate that the decarboxylation and oxygenation involves the formation

  本文报道了一种使用非血红素锰催化剂在蓝光照射下以 O 2作为唯一氧化剂的羧酸脱羧氧化的新方案。该协议具有温和的反应条件，可将现成的羧酸转化为各种有价值的醛、酮和酰胺。机理研究表明，脱羧和氧化涉及活性锰氧物质的形成。