9,12-十八碳二烯醛 | 2541-61-9

• 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: 9,12-十八碳二烯醛
• 英文名称: (9Z,12Z)-octadeca-9,12-dienal
• 英文别名: (Z,Z)-9,12-octadecadienal；linoleylaldehyde
• CAS: 2541-61-9
• 化学式: C₁₈H₃₂O
• 分子量: 264.451
• InChiKey: HXLZULGRVFOIDK-HZJYTTRNSA-N

物化性质

• 保留指数：
  1970;1971

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 室温 |

反应信息

• 作为反应物：
  描述：

  9,12-十八碳二烯醛 在 LCA(long chain aldehydes)-forming activity in Ulva pertusa fronds solubilized by Triton X-100 作用下， 反应 0.25h， 生成 (8Z,11Z)-8,11-heptadecadienal
  参考文献：
  名称：

  在绿藻 Ulva pertusa 中产生长链醛的酶系统的特异性

  摘要：

  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。

  DOI：

  10.1016/0031-9422(89)80021-4
• 作为产物：
  描述：

  亚油酸甲酯 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 9,12-十八碳二烯醛
  参考文献：
  名称：

  Design and synthesis of protein kinase C epsilon selective diacylglycerol lactones (DAG-lactones)

  摘要：

  DAG-lactones afford a synthetically accessible, high affinity platform for probing structure activity relationships at the Cl regulatory domain of protein kinase C (PKC). Given the central role of PKC isoforms in cellular signaling, along with their differential biological activities, a critical objective is the design of isoform selective ligands. Here, we report the synthesis of a series of DAG-lactones varying in their side chains, with a particular focus on linoleic acid derivatives. We evaluated their selectivity for PKC epsilon versus PKC alpha both under standard lipid conditions (100% phosphatidylserine, PS) as well as in the presence of a nuclear membrane mimetic lipid mixture (NML). We find that selectivity for PKC epsilon versus PKC alpha tended to be enhanced in the presence of the nuclear membrane mimetic lipid mixture and, for our lead compound, report a selectivity of 32-fold. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.025

文献信息

• Selective Hydrosilylation of Esters to Aldehydes Catalysed by Iridium(III) Metallacycles through Trapping of Transient Silyl Cations
  作者：Yann Corre、Vincent Rysak、Frédéric Capet、Jean-Pierre Djukic、Francine Agbossou-Niedercorn、Christophe Michon

  DOI：10.1002/chem.201602867

  日期：2016.9.19

  The combination of an iridium(III) metallacycle and 1,3,5‐trimethoxybenzene catalyses rapidly and selectively the reduction of esters to aldehydes at room temperature with high yields through hydrosilylation followed by hydrolysis. The ester reduction involves the trapping of transient silyl cations by the 1,3,5‐trimethoxybenzene co‐catalyst, supposedly by formation of an arenium intermediate whose

  铱（III）金属环与1,3,5-三甲氧基苯的组合可在室温下快速催化并选择性地将酯还原为醛，并通过氢化硅烷化和水解反应高收率。酯的还原涉及被1,3,5-三甲氧基苯助催化剂捕获瞬态甲硅烷基阳离子，据推测是由于形成了芳烃中间体，其作用已通过DFT计算得以解决。
• PRODUCTION OF CYCLIC ACETALS BY REACTIVE DISTILLATION
  申请人：Billodeaux Damon Ray

  公开号：US20120330034A1

  公开（公告）日：2012-12-27

  Cyclic acetals can be produced in a reactive distillation apparatus by combining a polyhydroxyl compound and an aldehyde. High concentrations of cyclic acetals are removed as liquid products from the column while water is removed as an overhead vapor stream.

  环状缩醛可以通过在反应蒸馏设备中将多羟基化合物和醛类化合物结合而制备。高浓度的环状缩醛作为液体产品从塔柱中移除，而水则作为顶部蒸汽流从中移除。
• PRODUCTION OF CYCLIC ACETALS OR KETALS USING SOLID ACID CATALYSTS
  申请人：Terrill Daniel Latham

  公开号：US20120330032A1

  公开（公告）日：2012-12-27

  A process for making a cyclic compounds such as cyclic acetal or cyclic ketones by feeding aldehyde or ketone compounds and polyhydroxyl compounds to a reaction zone at a molar ratio of polyhydroxyl compounds to aldehyde or ketone compounds of at least 3:1, reacting these compounds in the presence of a solid acid such as an acidic ion exchange resin, to generate a liquid reaction mixture without separating water from the reaction mixture as it is being formed in the reaction mixture, withdrawing the liquid reaction mixture from the reaction zone as a liquid product stream, and feeding the liquid reaction product stream to a distillation column to separate cyclic acetal compounds from unreacted polyhydroxyl compounds, and optionally recycling back the unreacted polyhydroxyl compounds to the reaction zone. The process produces cyclic acetal compounds in yields of at least 90% with long catalyst life. The process is also suitable to make cyclic ketals from ketone compounds.

  通过将醛或酮化合物和多羟基化合物以多羟基化合物与醛或酮化合物的摩尔比至少为3:1的比例送入反应区域，在固体酸的存在下（如酸性离子交换树脂）中反应这些化合物，生成液体反应混合物而不将水从反应混合物中分离出来，将液体反应混合物从反应区域中作为液体产品流撤出，并将液体反应产物流送入蒸馏塔以从未反应的多羟基化合物中分离出环状缩醛化合物，并可选择性地将未反应的多羟基化合物回收到反应区域。该过程以至少90%的产率生产环状缩醛化合物，并具有长寿命的催化剂。该过程也适用于从酮化合物制备环状缩酮。
• PRODUCTION OF CYCLIC ACETALS OR KETALS USING LIQUID-PHASE ACID CATALYSTS
  申请人：Terrill Daniel Latham

  公开号：US20120330033A1

  公开（公告）日：2012-12-27

  A process for making a cyclic compounds such as cyclic acetal or cyclic ketones by feeding aldehyde or ketone compounds and polyhydroxyl compounds to a reaction vessel at a molar ratio of polyhydroxyl compounds to aldehyde or ketone compounds of at least 3:1, reacting these compounds in the presence of a homogeneous acid catalyst to generate a liquid phase homogeneous reaction mixture containing the acid catalyst without separating water from the reaction mixture as it is being formed in the reaction mixture, withdrawing the liquid phase homogeneous reaction mixture from the reaction vessel as a liquid product stream, and feeding the liquid reaction product stream to a distillation column to separate cyclic acetal compounds from unreacted polyhydroxyl compounds, and optionally recycling back the unreacted polyhydroxyl compounds and/or acid catalyst to the reaction vessel. The process produces cyclic acetal compounds in high yields. The process is also suitable to make cyclic ketals from ketone compounds.

  通过将醛或酮化合物和多羟基化合物以多羟基化合物与醛或酮化合物的摩尔比至少为3:1的比例加入到反应容器中，通过在均相酸催化剂存在下反应这些化合物，生成含有酸催化剂的液相均相反应混合物，而不从反应混合物中分离水，将液相均相反应混合物从反应容器中作为液体产品流撤出，并将液体反应产物流送入蒸馏塔以将环状缩醛化合物与未反应的多羟基化合物分离，并可选择性地将未反应的多羟基化合物和/或酸催化剂回收到反应容器中。该过程以高产率生产环状缩醛化合物。该过程也适用于从酮化合物制备环状缩酮。
• 一种氨基脂质化合物及其制备方法和用途
  申请人：深圳深信生物科技有限公司

  公开号：CN112961091B

  公开（公告）日：2022-06-17

  本发明涉及一种氨基脂质化合物，化学式I所示的化合物、或其立体异构体、或其互变异构体、或其药学上可接受的盐，同时还公开了该化合物的制备方法以及其作为递送治疗剂组分和在制备药物中的用途。

表征谱图