3,7-二甲基-6-辛烯酰氯 | 36392-06-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 3,7-二甲基-6-辛烯酰氯
• 英文名称: citronellic acid chloride
• 英文别名: citronelloyl chloride；3,7-dimethyloct-6-enoyl chloride
• CAS: 36392-06-0
• 化学式: C₁₀H₁₇ClO
• 分子量: 188.697
• InChiKey: NOXCOFIBMWWGPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  3,7-二甲基-6-辛烯酰氯 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 0.5h， 以59%的产率得到5-甲基-2-异丙基环己酮
  参考文献：
  名称：

  Acyl radicals: intermolecular and intramolecular alkene addition reactions

  摘要：

  A full study of the use of phenyl selenoesters as precursors to acyl radicals and their subsequent participation in intermolecular and intramolecular alkene addition reactions is detailed. Primary alkyl-, vinyl-, and aryl-substituted acyl radicals generated by Bu3SnH treatment of the corresponding phenyl selenoesters participate cleanly in intermolecular addition reactions with alkenes bearing electron-withdrawing or radical-stabilizing substituents at rates that exceed those of the potentially competitive decarbonylation or reduction. Similarly, their intramolecular addition to activated or unactivated alkenes proceeds without significant competitive reduction or decarbonylation and at rates generally greater-than-or-equal-to 1 x 10(6) s-1 with some occurring at rates greater-than-or-equal-to 3 x 10(7) s-1. Consistent with their behavior in intermolecular addition reactions, the 5-exo-trig cyclizations of secondary and tertiary alkyl-substituted acyl radicals to an unactivated olefin acceptor may be accompanied by varying degrees of decarbonylation, even under low-temperature free-radical reaction conditions. Studies are presented which suggest that the intramolecular additions of acyl radicals to alkenes under the conditions detailed herein may be regarded as irreversible, kinetically controlled processes which exhibit regioselectivity that is predictable based on well-established empirical rules set forth for the analogous free-radical cyclization reactions of alkyl radicals.

  DOI：

  10.1021/jo00031a021
• 作为产物：
  描述：

  magnesium,2-methylpent-2-ene,bromide 在 copper(l) iodide 、 氯化亚砜 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.0h， 生成 3,7-二甲基-6-辛烯酰氯
  参考文献：
  名称：

  β-甲基-β-丙内酯开环反应合成萜烯的新方法

  摘要：

  研究了萜烯合成的新途径，该途径通过萜烯羧酸作为关键中间体，通过在铜催化剂存在下用铜酸盐或格氏试剂与β-甲基-β-丙内酯的区域特异性开环而获得。

  DOI：

  10.1016/0040-4039(80)80126-2

文献信息

• Inhibitors of Acyl-CoA:Cholesterol O-Acyl Transferase (ACAT) as Hypocholesterolemic Agents. 8. Incorporation of Amide or Amine Functionalities into a Series of Disubstituted Ureas and Carbamates. Effects on ACAT Inhibition in vitro and Efficacy in vivo
  作者：Patrick M. O'Brien、Drago R. Sliskovic、C. John Blankley、Bruce. D Roth、Michael W. Wilson、Katherine L. Hamelehle、Brian R. Krause、Richard L. Stanfield

  DOI：10.1021/jm00038a010

  日期：1994.6

  A series of disubstituted ureas containing amide or amine groups was prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyl transferase in vitro and to lower plasma total cholesterol in a variety of cholesterol-fed rat models in vivo. The presence of polar or ionizable functionalities within this class of compounds may impart greater aqueous solubility to those compounds and

  制备了一系列含有酰胺基或胺基的双取代脲，并评估了它们在体外抑制酰基-CoA：胆固醇O-酰基转移酶的能力以及在体内各种由胆固醇喂养的大鼠模型中降低血浆总胆固醇的能力。这类化合物中极性或可电离官能团的存在可以赋予这些化合物更大的水溶性，从而改善向肠道小肠细胞内酶位置的转运。即使是在水性媒介物中给药，这类化合物在慢性胆固醇喂养的高胆固醇血症大鼠模型中也能降低胆固醇。通常，在高胆固醇血症的急性大鼠模型中，含胺化合物比酰胺更有效和有效。进一步的结构活性关系研究表明，酰胺/胺基团的优选位置是尿素部分的β，而不是α，并且在该系列中，要获得良好的体外效果，必须存在仲胺（或酰胺）质子效力。这些化合物之一9n（-）在水性介质中给药给预先建立的高胆固醇血症的大鼠时，可降低血浆总胆固醇（-47％）和提高高密度脂蛋白胆固醇（+ 256％）。
• Tributyltin Hydride in NMP-Promoted Reduction of Acid Chlorides to Aldehydes under Transition-Metal-Free Conditions
  作者：Abdallah Hamze、Mouâd Alami、Patrick Le Ménez、Olivier Provot、Jean-Daniel Brion

  DOI：10.1055/s-0029-1219796

  日期：2010.4

  Abstract: Tributyltin hydride in N -methyl-2-pyrrolidinone (NMP)was used for the partial reduction of various functionalized acidchlorides at room temperature. This transition-metal-free procedureallows the synthesis of a range of (hetero)aromatic- and aliphatic al-dehydes in good to excellent yields. Key words: acid chlorides, aldehydes, reduction, tributyltin hy-dride, N -methyl-2-pyrrolidinone,

  摘要：N-甲基-2-吡咯烷酮（NMP）中的三丁基氢化锡用于室温下部分还原各种官能化酰氯。这种不含过渡金属的程序允许以良好到极好的收率合成一系列（杂）芳香族和脂肪族醛。关键词：酰氯，醛，还原，三丁基氢化锡，N-甲基-2-吡咯烷酮，游离金属条件理想的工具。在过去的几十年中，已经开发了多种方法。除了传统的 Pd/BaSO 4 氢解（罗森蒙德还原）外，1 许多金属氢化物已广泛用于此类转化，包括三叔丁氧基氢化铝锂或钠，2硼氢化钠，3高价硅氢化物，4过渡金属硼氢化物，5阴离子过渡金属还原剂，6等。7 然而，这些方法有局限性，包括过度还原、缺乏通用性、产量低和官能团不兼容。替代方法包括使用有机硅
• Reductive couplings of acid chlorides mediated by SmI2
  作者：J. Collin、F. Dallemer、J.L. Namy、H.B. Kagan

  DOI：10.1016/s0040-4039(00)70710-6

  日期：1989.1

  Reductive couplings of acid chlorides and of acid chlorides with aldehydes or ketones in presence of an excess of SmI2 produce ketones in moderate to good yields.

  在过量的SmI 2的存在下，酰氯和酰氯与醛或酮的还原偶联以中等至良好的产率产生酮。
• Synthesis and Biological Evaluation of Novel Phosphatidylcholine Analogues Containing Monoterpene Acids as Potent Antiproliferative Agents
  作者：Anna Gliszczyńska、Natalia Niezgoda、Witold Gładkowski、Marta Czarnecka、Marta Świtalska、Joanna Wietrzyk

  DOI：10.1371/journal.pone.0157278

  日期：——

  The synthesis of novel phosphatidylcholines with geranic and citronellic acids in sn-1 and sn-2 positions is described. The structured phospholipids were obtained in high yields (59–87%) and evaluated in vitro for their cytotoxic activity against several cancer cell lines of different origin: MV4-11, A-549, MCF-7, LOVO, LOVO/DX, HepG2 and also towards non-cancer cell line BALB/3T3 (normal mice fibroblasts). The phosphatidylcholines modified with monoterpene acid showed a significantly higher antiproliferative activity than free monoterpene acids. The highest activity was observed for the terpene-phospholipids containing the isoprenoid acids in sn-1 position of phosphatidylcholine and palmitic acid in sn-2.

  报道了在sn-1和sn-2位置上含有香叶酸和香茅酸的新型磷脂酰胆碱的合成。这些结构化磷脂以高产率（59-87%）获得，并在体外对其对几种不同来源的癌细胞系的细胞毒性活性进行了评估：MV4-11、A-549、MCF-7、LOVO、LOVO/DX、HepG2，以及对非癌细胞系BALB/3T3（正常小鼠成纤维细胞）。与游离单萜酸相比，修饰有单萜酸的磷脂酰胆碱显示出显著更高的抗增殖活性。含有磷脂酰胆碱sn-1位置上的异戊二烯酸和sn-2位置上的棕榈酸的萜类磷脂显示出最高的活性。
• [EN] LIPID NANOPARTICLE FORMULATIONS<br/>[FR] FORMULATIONS DE NANOPARTICULES LIPIDIQUES
  申请人：ACUITAS THERAPEUTICS INC

  公开号：WO2018081480A1

  公开（公告）日：2018-05-03

  Improved formulations of lipid nanoparticles are provided. Use of the lipid nanoparticles for delivery of a therapeutic agent and methods for their preparation are also provided.

  提供了改进的脂质纳米粒子配方。还提供了利用这些脂质纳米粒子传递治疗剂的方法以及它们的制备方法。