(Z)-1-chlorononadec-10-en-2-one | 177987-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-1-chlorononadec-10-en-2-one
• 英文别名: 1-Chlorononadec-10-en-2-one
• CAS: 177987-16-5
• 化学式: C₁₉H₃₅ClO
• 分子量: 314.939
• InChiKey: TXWLMBAFUCXMER-KTKRTIGZSA-N

物化性质

• 沸点：
  417.1±28.0 °C(Predicted)
• 密度：
  0.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  咪唑 、 (Z)-1-chlorononadec-10-en-2-one 以 乙腈 为溶剂， 反应 5.0h， 以65%的产率得到(Z)-1-(1H-imidazol-1-yl)nonadec-10-en-2-one
  参考文献：
  名称：

  Cu催化有氧氧化酰胺化由α-取代甲基酮合成脂肪族α-酮酰胺

  摘要：

  α-酮酰胺是一个重要的关键官能团，已被用作多种官能团转化中的通用且有价值的中间体和合成子。通过金属催化的好氧氧化酰胺化，制备芳基α-酮酰胺作为候选药物的合成方法得到了极大的改进。然而，尚未报道通过金属催化的需氧氧化酰胺化制备烷基α-酮酰胺，因为从理论上具有两个α-碳的脂肪族酮生成α-酮酰胺提供了两种不同的α-酮酰胺。我们的策略是通过引入N来激活 α-碳-在两个α位之一的取代基。该策略的关键是杂环化合物如三唑和咪唑如何影响烷基α-酮酰胺合成的选择性。从这个基本概念出发，通过优化反应和阐明通过铜催化的好氧氧化酰胺化合成芳基 α-酮酰胺的机理，我们以高产率（48-84%）制备了 14 种脂肪族 α-酮酰胺。

  DOI：

  10.1039/d1ob00129a
• 作为产物：
  描述：

  cis-1-diazo-2-oxo-10-nonadecene 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.17h， 以92%的产率得到(Z)-1-chlorononadec-10-en-2-one
  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

• INHIBITORS OF OLEAMIDE HYDROLASE
  申请人：The Scripps Research Institute

  公开号：EP0910561B1

  公开（公告）日：2004-04-07
• US5856537A
  申请人：——

  公开号：US5856537A

  公开（公告）日：1999-01-05
• US6096784A
  申请人：——

  公开号：US6096784A

  公开（公告）日：2000-08-01
• Inhibition of Oleamide Hydrolase Catalyzed Hydrolysis of the Endogenous Sleep-Inducing Lipid <i>cis</i>-9-Octadecenamide
  作者：Jean E. Patterson、Ian R. Ollmann、Benjamin F. Cravatt、Dale L. Boger、Chi -Huey Wong、Richard A. Lerner

  DOI：10.1021/ja954064z

  日期：1996.1.1

  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.
• Synthesis of aliphatic α-ketoamides from α-substituted methyl ketones <i>via</i> a Cu-catalyzed aerobic oxidative amidation
  作者：Hyojin Cha、Jin Young Chai、Hyeong Baik Kim、Dae Yoon Chi

  DOI：10.1039/d1ob00129a

  日期：——

  for making aryl α-ketoamides as drug candidates have been greatly improved through metal-catalyzed aerobic oxidative amidations. However, the preparation of alkyl α-ketoamides through metal-catalyzed aerobic oxidative amidations has not been reported because generating α-ketoamides from aliphatic ketones with two α-carbons theoretically provides two distinct α-ketoamides. Our strategy is to activate

  α-酮酰胺是一个重要的关键官能团，已被用作多种官能团转化中的通用且有价值的中间体和合成子。通过金属催化的好氧氧化酰胺化，制备芳基α-酮酰胺作为候选药物的合成方法得到了极大的改进。然而，尚未报道通过金属催化的需氧氧化酰胺化制备烷基α-酮酰胺，因为从理论上具有两个α-碳的脂肪族酮生成α-酮酰胺提供了两种不同的α-酮酰胺。我们的策略是通过引入N来激活 α-碳-在两个α位之一的取代基。该策略的关键是杂环化合物如三唑和咪唑如何影响烷基α-酮酰胺合成的选择性。从这个基本概念出发，通过优化反应和阐明通过铜催化的好氧氧化酰胺化合成芳基 α-酮酰胺的机理，我们以高产率（48-84%）制备了 14 种脂肪族 α-酮酰胺。