9-dodecen-1-ol | 91856-11-0

• 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: 9-dodecen-1-ol
• 英文别名: dodec-9-en-1-ol
• CAS: 91856-11-0
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: GJNNIRNIXNLOJP-UHFFFAOYSA-N

物化性质

• 熔点：
  77.27°C (estimate)
• 沸点：
  283.3°C (estimate)
• 密度：
  0.8597 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-dodecen-1-ol 在 四氮唑 、 sulfur 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 thiophosphoric acid O,O'-bis-(2-cyanoethyl) ester O''-dodec-9-enyl ester
  参考文献：
  名称：

  Synthesis, Structure−Activity Relationships, and Biological Evaluation of Fatty Alcohol Phosphates as Lysophosphatidic Acid Receptor Ligands, Activators of PPARγ, and Inhibitors of Autotaxin

  摘要：

  We previously reported that fatty alcohol phosphates (FAP) represent a minimal pharmacophore required to interact with lysophosphatidic acid (LPA) receptors. To improve the activity of the first-generation saturated FAP series, a structure-activity relationship (SAR) study was carried out that includes modifications to the headgroup and alkyl side chain of the FAP pharmacophore. A series of unsaturated (C-10-C-18) FAP, headgroup-modified hydrolytically stable saturated (C-10-C-18) alkyl phosphonates, and saturated and unsaturated (C-10-C-18) thiophosphate analogues were synthesized and evaluated for activity in RH7777 cells transfected with individual LPA(1-3) receptors, in PC-3 cells and in human platelets that endogenously express all three isoforms. In this series we identified several LPA(1)- and LPA(3)-selective antagonists with IC50 values in the nanomolar range. Oleoyl-thiophosphate (15g) was shown to be a panagonist, whereas tetradecyl-phosphonate (16c) was identified as a pan-antagonist. These compounds were also tested for the ability to activate the transcription factor PPAR gamma, an intracellular receptor for LPA, in CV1 cells transfected with the PPRE-Acox-Rluc reporter gene. All the FA-P tested, along with the previously reported LPA GPCR antagonists dioctanoyl glycerol pyrophosphate (2), Ki16425 (6), and the agonist OMPT (3), were activators of PPAR gamma. The pan-agonist oleoyl-thiophosphate (15g) and pan-antagonist tetradecyl-phosphonate (16c) mimicked LPA in inhibiting autotaxin, a secreted lysophospholipase D that produces LPA in biological fluids.

  DOI：

  10.1021/jm049609r
• 作为产物：
  描述：

  9-溴-1-壬醇 在 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.5h， 生成 9-dodecen-1-ol
  参考文献：
  名称：

  Synthesis of insect sex pheromones and their homologues. 2. A convenient method for synthesizing (Z)-alkenols and their acetates.

  摘要：

  通过一种简便的方法，利用Wittig反应将（ω-羟基烷基）三苯基膦盐与烷基醛反应，合成了（Z）-烯醇及其乙酸酯。通过涂有CHDMS的玻璃毛细管柱进行GC分析，评估产物的几何纯度不小于95%的（Z）构型。

  DOI：

  10.1271/bbb1961.44.257

文献信息

• [EN] PREPARATION OF AMINO ACIDS AND AMINO ACID DERIVATIVES<br/>[FR] PRÉPARATION D'ACIDES AMINÉS ET DE DÉRIVÉS D'ACIDES AMINÉS
  申请人：MATERIA INC

  公开号：WO2018057290A1

  公开（公告）日：2018-03-29

  The invention relates to a method for synthesizing amino acids or amino acid derivatives involving cross metathesis of functionalized olefins and a tandem amination-reduction process. Amino acids and amino acid derivatives present many interesting physical and chemical properties finding many uses in the automotive, fuel, electronic, and textile industries.

  这项发明涉及一种合成氨基酸或氨基酸衍生物的方法，包括功能化烯烃的交叉复分解以及串联氨基化-还原过程。氨基酸和氨基酸衍生物具有许多有趣的物理和化学性质，在汽车、燃料、电子和纺织工业中找到了许多用途。
• [EN] SYNTHESIS OF STRAIGHT-CHAIN LEPIDOPTERAN PHEROMONES THROUGH ONE- OR TWO- CARBON HOMOLOGATION OF FATTY ALKENES<br/>[FR] SYNTHÈSE DE PHÉROMONES DE LÉPIDOPTÈRES À CHAÎNE DROITE PAR HOMOLOGATION D'UN OU DEUX ATOMES DE CARBONE D'ALCÈNES GRAS
  申请人：PROVIVI INC

  公开号：WO2020018581A1

  公开（公告）日：2020-01-23

  Methods for the preparation of alkenes including insect pheromones are described. The methods include homologation reactions employing reagents such as 1,3-diesters, epoxides, cyanoacetates, and cyanide salts for elongation of starting materials and intermediates by one or two carbon atoms. The alkenes include insect pheromones useful in a number of agricultural applications.

  描述了制备烯烃（包括昆虫信息素）的方法。这些方法包括使用1,3-二酯、环氧化物、氰乙酸盐和氰化物等试剂进行同系反应，通过增加一到两个碳原子来延长起始物质和中间体。这些烯烃包括在许多农业应用中有用的昆虫信息素。
• PRODUCTION OF FATTY OLEFIN DERIVATIVES VIA OLEFIN METATHESIS
  申请人：PROVIVI, INC.

  公开号：US20170137365A1

  公开（公告）日：2017-05-18

  In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R 1 is independently selected from H, C 1-18 alkyl, and C 2-18 alkenyl; R 2b is C 1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.

  在一个方面，该发明提供了一种合成脂肪烯衍生物的方法。该方法包括：a）在存在一种烯烃催化剂的条件下，将符合式I的烯烃与符合式IIb的交换反应伙伴接触，以形成符合式IIIb的交换产物；并b）将交换产物转化为脂肪烯衍生物。每个R1独立地选择自H、C1-18烷基和C2-18烯基；R2为C1-8烷基；下标y为0至17之间的整数；下标z为0至17之间的整数。在某些实施方式中，交换催化剂为钨催化剂或钼催化剂。在各种实施方式中，脂肪烯衍生物为信息素。还描述了信息素组合物及其使用方法。
• Method for Producing Aldehyde and Ketone
  申请人：Yamashita Miyoshi

  公开号：US20110282102A1

  公开（公告）日：2011-11-17

  Provided is a highly efficient method for the production of aldehydes and ketones, which is inexpensive, exhibits high reactivity, and is capable of easy separation of byproduct after the reaction. More particularly, there is provided a method for producing an aldehyde or a ketone, comprising at least an oxidation step of oxidizing a primary alcohol or a secondary alcohol in the presence of a polymeric carbodiimide represented by the following formula (1) and having a weight-average molecular weight of 300 to 5000, and a sulfoxide compound, together with an acid and a base, or together with a salt of the acid and the base.

  提供了一种高效的生产醛和酮的方法，该方法廉价、具有高反应性，并能够在反应后轻松分离副产物。更具体地，提供了一种生产醛或酮的方法，包括至少一个氧化步骤，即在聚合物碳二亚胺（表示为以下式（1）且具有分子量为300至5000的重均分子量）和亚砜化合物的存在下氧化一级醇或二级醇，以及酸和碱，或者酸和碱的盐。
• AGRICULTURAL PHEROMONE COMPOSITIONS COMPRISING POSITIONAL ISOMERS
  申请人：PROVIVI, INC.

  公开号：US20170135343A1

  公开（公告）日：2017-05-18

  The present disclosure provides pheromone compositions. In some aspects, the compositions taught herein comprise a pheromone chemically corresponding to the pheromone naturally produced by a given insect, along with at least one positional isomer of said pheromone. In various aspects, pheromone compositions of the present disclosure are able to modulate the response of the insect based on the ratio of natural pheromone to its positional isomer.

  本公开提供信息素组合物。在某些方面，本文所教授的组合物包括一种与某种昆虫自然产生的信息素在化学上相对应的信息素，以及至少一种该信息素的位置异构体。在各个方面，本公开的信息素组合物能够通过自然信息素与其位置异构体的比例来调节昆虫的反应。