2-氯油酸 | 106092-90-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-氯油酸
• 英文名称: 2-chlorooleic acid
• 英文别名: (Z)-2-chlorooctadec-9-enoic acid
• CAS: 106092-90-4
• 化学式: C₁₈H₃₃ClO₂
• 分子量: 316.912
• InChiKey: KTTLEIOEBUVYMY-KTKRTIGZSA-N

物化性质

• 沸点：
  402.5±33.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯油酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (Z)-2-chlorooctadec-9-enoyl chloride
  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：

  油酸 在 四氯化碳 、 lithium diisopropyl amide 作用下， 生成 2-氯油酸
  参考文献：
  名称：

  Preparation of unsaturated .alpha.-chloro acids and intramolecular [2 + 2] cycloadditions of the chloroketenes derived from them

  摘要：

  DOI：

  10.1021/jo00378a036

文献信息

• [EN] INHIBITORS OF OLEAMIDE HYDROLASE<br/>[FR] INHIBITEURS DE L'OLEAMIDE HYDROLASE
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：WO1997049667A1

  公开（公告）日：1997-12-31

  (EN) Inhibitors of oleamide hydrolase, responsible for the hydrolysis of an endogenous sleep-inducing lipid (1, $i(cis)-9-octadecenamide) were designed and synthesized. The most potent inhibitors possess an electrophilic carbonyl group capable of reversibly forming a (thio) hemiacetal or (thio) hemiketal to mimic the transition state of a serine or cysteine protease catalyzed reaction. In particular, the tight binding $g(a)-keto ethyl ester 8 (1.4 nM) and the trifluoromethyl ketone inhibitor 12 (1.2 nM) were found to have exceptional inhibitory activity. In addition to the inhibitory activity, some of the inhibitors displayed agonist activity which resulted in the induction of sleep in laboratory animals.(FR) L'invention porte sur la conception et la synthèse d'inhibiteurs de l'oléamide hydrolase responsables de l'hydrolyse d'un lipide endogène provoquant le sommeil (1, $i(cis)-9-octadécènamide). Les inhibiteurs les plus puissants possèdent un groupe carbonyle électrophile capable de constituer de façon réversible un (thio) hémi-acétal ou (thio) hémi-cétal simulant l'état de transition d'une réaction catalysée par la sérine ou cystéine protéase. Il a été découvert en particulier que le $g(a)-céto-éthyl ester 8 (1,4 nM) à liaison renforcée et l'inhibiteur trifluorométhyl cétone 12 (1,2 nM) avaient une activité inhibitrice exceptionnelle. Outre leur activité inhibitrice, certains des inhibiteurs ont montré une activité agoniste ayant pour résultat d'induire le sommeil chez des animaux de laboratoire.

  (中) 设计并合成了一种抑制剂，其作用是抑制内源性诱导睡眠的脂质（1，$i(cis)-9-十八碳烯酰胺）的水解酶（oleamide hydrolase）。最有效的抑制剂具有亲电性羰基基团，能够可逆地形成（硫）半乙缩醛或（硫）半缩酮，以模拟丝氨酸或半胱氨酸蛋白酶催化反应的过渡态。特别是紧密结合的$g(a)-酮乙酯8（1.4 nM）和三氟甲基酮抑制剂12（1.2 nM）具有出色的抑制活性。除了抑制活性外，一些抑制剂还表现出激动剂活性，导致实验动物的睡眠诱导。
• New lysosphingolipid derivatives
  申请人：FIDIA S.p.A.

  公开号：EP0373038A2

  公开（公告）日：1990-06-13

  Novel derivatives of lysophingolipids free from sialic acids which are N-acyllysosphingolipids having one of the two formulae: in which -A- stands for the group -CH=CH- or -CH₂-CH₂-, n₁ is a whole number of between 6 and 18, n₂ a whole number of between 11 and 15, X is a hydrogen atom or the residue of a monosaccharide or a disaccharide or phosphorylcholine and R represents an alkyl radical derived from a saturated or unsaturated aliphatic carboxylic acid having from 2 to 24 carbon atoms substituted by one or more polar groups. The lysosphingolipid derivatives of the invention exhibit an inhibiting action on protein-kinase C activation and, thus, can be utilized in therapies for various pathologies of the nervous system.

  不含硅酸的溶血鞘磷脂新衍生物，属于具有以下两种式子之一的 N-酰基鞘磷脂： 其中 -A- 代表基团 -CH=CH- 或 -CH₂-CH₂-，n₁ 是介于 6 和 18 之间的整数，n₂ 是介于 11 和 15 之间的整数、X 是氢原子或单糖、双糖或磷酸胆碱的残基，R 代表烷基，衍生自具有 2 至 24 个碳原子的饱和或不饱和脂肪族羧酸，并被一个或多个极性基团取代。本发明的溶血磷脂衍生物对蛋白激酶 C 的活化具有抑制作用，因此可用于治疗神经系统的各种病症。
• Composition and a process for a preparation of polyurethane dispersion
  申请人：PTT Global Chemical Public Company Limited

  公开号：US10584090B2

  公开（公告）日：2020-03-10

  This invention relates to a composition for a preparation of polyurethane dispersion, comprising bio-based polyol as shown in structure (I) and polyhydroxy fatty acid compound as shown in structure (II): wherein, R represents a polyhydric alcohol unit that is selected from aliphatic polyhydric alcohol, alicyclic polyhydric alcohol, cyclic polyhydric alcohol, aromatic polyhydric alcohol, or optionally, cyclic polyhydroxyl having heteroatom; R\ represents a hydrocarbon unit obtained from a molecular chain of unsaturated fatty acid having 14-24 carbon atoms and having from 1-6 pairs of vicinal diol group per one molecular chain of such unsaturated fatty acid; n represents an integer from 2 to 8 of an ester group obtained from a reaction of polyhydric alcohol and unsaturated fatty acid; wherein said composition is prepared from a process comprising the steps of: i. mixing fatty acid comprising unsaturated fatty acid and polyhydric alcohol at a ratio of 1 mole equivalent or more of carboxylic group from unsaturated fatty acid per a hydroxy group from polyhydric alcohol; ii. adding organic acid and peroxide compound into the mixture from step i.; iii. adding nucleophilic substance into the mixture from step ii. under acidic condition.

  本发明涉及一种用于制备聚氨酯分散体的组合物，该组合物由结构(I)所示的生物基多元醇和结构(II)所示的多羟基脂肪酸化合物组成：其中，R 代表选自脂肪族多羟基化合物、脂环族多羟基化合物、环状多羟基化合物、芳香族多羟基化合物或可选的具有杂原子的环状多羟基化合物的多羟基单元；R 代表从具有 14-24 个碳原子的不饱和脂肪酸分子链中获得的烃单元，该不饱和脂肪酸的每一条分子链中具有 1-6 对邻位二元醇基团；n 代表从多元醇和不饱和脂肪酸反应中获得的酯基的 2 到 8 的整数； 其中，所述组合物是由包括以下步骤的工艺制备的：i.将包含不饱和脂肪酸和多羟基乙醇的脂肪酸以不饱和脂肪酸的羧基与多羟基乙醇的羟基 1 摩尔当量或更高的比例混合； ii.
• Novel synthetic gangliosides
  申请人：Neuronyx, Inc.

  公开号：US20020072502A1

  公开（公告）日：2002-06-13

  Disclosed is a synthetic ganglioside comprising a deamino-(2-O-substituted)-sphingosine group. Preferably, the deamino-(2-O-substituted)-sphingosine group is represented by Structural Formula (I): 1 X is ═O or —H 2 . R 1 and R 2 are independently a substituted or unsubstituted straight chain or branched hydrocarbyl group, wherein the hydrocarbyl group optionally comprises —S—, —S(O)—, —SO 2 —, —O— —NHCO—, —CONH—, —C(O)O—, —OC(O)—or —NR—. R 3 is —H, —OS(O) 2 OH, —OP(O) 2 OH, —OP(O) 2 OP(O) 2 OH, —ON(O)OH. Each R is independently —H, an aliphatic group, a substituted aliphatic group, an aryl group or a substituted aryl group. Also disclosed are methods of treating a subject with a neurological condition or disease and methods of treating a subject in need of immunosuppresion. The methods comprises the step of administering to the subject an effective amount of the synthetic ganglioside represented by Structural Formula (I).

  本发明公开了一种合成神经节苷脂，它包含一个脱氨基-(2-O-取代)-肌球蛋白基团。优选地，脱氨基-(2-O-取代)-肌球蛋白基团由结构式（I）表示： 1 X 是 ═O 或 -H 2 . R 1 和 R 2 独立地为取代或未取代的直链或支链烃基，其中烃基可选地包括 -S-、-S(O)-、-SO 2 -、-O-、-NHCO-、-CONH-、-C(O)O-、-OC(O)-或-NR-。 R 3 是-H、-OS(O) 2 OH、-OP(O) 2 OH、-OP(O) 2 OP(O) 2 OH、-ON(O)OH。 每个 R 独立地为-H、脂肪族基团、取代的脂肪族基团、芳基或取代的芳基。 本发明还公开了治疗患有神经系统疾病的受试者的方法和治疗需要免疫抑制的受试者的方法。这些方法包括向受试者施用有效量的由结构式（I）代表的合成神经节苷脂的步骤。
• SNIDER B. B.; KULKARNI YASHWANT S., J. ORG. CHEM., 52,(1987) N 2, 307-310
  作者：SNIDER B. B.、 KULKARNI YASHWANT S.

  DOI：——

  日期：——