cyclohexadec-5-en-1-one | 21944-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexadec-5-en-1-one
• 英文别名: 5-cyclohexadecen-1-one；cyclohexadec-5-enone；5-cyclohexadecenone；ambretone；cyclohexadec-5-ene-1-one；5-Cyclohexadecen-1-on
• CAS: 21944-95-6；35951-24-7；37609-25-9
• 化学式: C₁₆H₂₈O
• 分子量: 236.398
• InChiKey: ABRIMXGLNHCLIP-UHFFFAOYSA-N

物化性质

• 熔点：
  36-37 °C
• 沸点：
  137 °C(Press: 0.5 Torr)
• 密度：
  0.863±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  cyclohexadec-5-en-1-one 在 palladium on carbon 、 盐酸羟胺 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.5h， 生成 cyclohexadecanone oxime
  参考文献：
  名称：

  Dansyl-labeled anionic amphiphile with a hexadecanoic carbon chain: Synthesis and detection for shape transitions in organized molecular assemblies

  摘要：

  The probing properties of a new fluorophore-labeled anionic surfactant, sodium 16-(N-dansyl)aminocetylate (16-DAN-ACA) were investigated systematically in molecular assemblies, especially in the transitions between micelles and vesicles. 16-DAN-ACA can efficiently differentiate the two different aggregate types in mixed cationic and anionic surfactant systems. The fluorescence anisotropy of 16-DAN-ACA was found to be sensitive for directly detecting the micellar growth in micelles containing oppositely charged surfactants; both cationic cetyltrimethylammonium bromide (CTAB) systems and anionic sodium dodecyl sulfate (SDS) systems were studied. The results indicated that the 16-DAN-ACA is a good fluorescent probe for differentiating the different aggregates, and even more can be used to detect the micellar growth. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.11.113
• 作为产物：
  描述：

  (E)-cyclotridec-2-enone 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， -78.0~620.0 ℃ 、4.0 Pa 条件下， 生成 cyclohexadec-5-en-1-one
  参考文献：
  名称：

  环丙基羰基自由基作为三碳插入单元：通过三碳环扩环容易合成C-15大环酮

  摘要：

  在FVP条件下于620°C进行的环状3-环丙基酮的热异构化为δ，ε-不饱和环烷酮提供了一条新的便捷途径。由廉价的C-12起始原料合成（±）-麝香酮已证明了这种新颖的三碳环扩环的合成潜力。

  DOI：

  10.1016/j.tetlet.2004.04.148

文献信息

• A Practical Method for Alcohol Oxidation with Aqueous Hydrogen Peroxide under Organic Solvent- and Halide-Free Conditions
  作者：Kazuhiko Sato、Masao Aoki、Junko Takagi、Klaus Zimmermann、Ryoji Noyori

  DOI：10.1246/bcsj.72.2287

  日期：1999.10

  A catalytic system consisting of sodium tungstate and methyltrioctylammonium hydrogensulfate effects oxidation of simple secondary alcohols to ketones using 3—30% H2O2 without any organic solvents. The oxidation can be conducted under entirely halide-free, mildly acidic conditions. A combination of tungstic acid and an appropriate quaternary ammonium salt also effects the alcohol dehydrogenation. The

  由钨酸钠和甲基三辛基硫酸氢铵组成的催化体系使用 3-30% 的 H2O2 在没有任何有机溶剂的情况下将简单的仲醇氧化成酮。氧化可以在完全不含卤化物的弱酸性条件下进行。钨酸和合适的季铵盐的组合也影响醇脱氢。有机/水双相反应允许容易的产物/催化剂分离。转化数，定义为每摩尔催化剂的产物摩尔数，接近 77700（2-辛醇）或 179000（1-苯基乙醇），比之前报道的任何数量级高两个数量级。酯、烷基和叔丁基二甲基甲硅烷基醚、环氧基、羰基、N-烷基甲酰胺和腈基团在反应条件下是可以耐受的。仲醇优先于末端烯烃氧化。伯链烷醇以中等至高产率直接氧化为羧酸。苯甲醇被选择性氧化成...
• Exaltone® (=Cyclopentadecanone) from Isomuscone® (=Cyclohexadecanone), a One-C-Atom Ring-Contraction Methodology via a Stereospecific Favorskii Rearrangement: Regioselective Application to (−)-(R)-Muscone
  作者：Christian Chapuis、Fabrice Robvieux、Carole Cantatore、Christine Saint-Léger、Laurent Maggi

  DOI：10.1002/hlca.201100398

  日期：2012.3

  Treatment of cyclohexadecanone (1g; with I2 (2.2 mol‐euqiv.) and KOH in MeOH) furnished the unsaturated (Z)‐ester 2g in 83% yield, via a stereospecific Favorskii rearrangement (Scheme 1). Further treatment with 3‐chloroperbenzoic acid (m‐CPBA) afforded the unreported epoxy ester 3g (88% yield), which was cleaved in 33% yield to Exaltone® (=cyclopentadecanone; 1f) with NaOH in MeOH/H2O and then HCl

  环己癸酮（1g ;用I 2（2.2 mol-euqiv。）和KOH在MeOH中的溶液）的处理通过立体定向Favorskii重排提供了2％的不饱和（Z）-酯2g（方案1）。用3-氯过苯甲酸（进一步处理米-CPBA），得到未报告的环氧酯3克（88％产率），将其在33％产率，以裂解Exaltone ®（=环十五; 1F）用NaOH在MeOH / H 2 O和然后HCl在65°。该方法类似地扩展到较高的温度（C 17）和较低的温度（C 15C 11）的环状酮类似物，以及对（-）-（R）-muscone（5c）和homomuscone（5f）的区域选择性（方案2）。相应的大环-1-氧杂螺的嗅觉特性[2，Ñ ]烷烃和烯烃4和8，从所得到的科里 Chaykovsky oxiranylation，还提出。
• Synthesis of bridged nicotinates having [n](2,5)pyridinophane skeletons (n=8–14)
  作者：Nobuhiro Kanomata、Shinsuke Yamada、Takayuki Ohhama、Akira Fusano、Yoshiharu Ochiai、Jun Oikawa、Masahiro Yamaguchi、Fumio Sudo

  DOI：10.1016/j.tet.2006.02.002

  日期：2006.4

  Synthesis of various bridged nicotinates 6 having [n](2,5)pyridinophane skeletons (n=8–14) was accomplished by the unique pyridine-formation reaction of methyl propiolate with a series of formyl-substituted (vinylimino)phosphoranes 5, which were prepared from the corresponding cycloalkanones 1 via Vilsmeier–Haack formylation giving chloro-substituted cycloalkenals 2, their thermal and photochemical

  各个桥接烟酸酯的合成6具有[ Ñ ]（2,5）pyridinophane骨架（Ñ = 8-14）是通过用一系列甲酰基-取代的（vinylimino）的丙炔酸甲酯的独特吡啶形成反应完成膦5，其由相应的环烷酮1通过Vilsmeier-Haack甲酰化制备，得到氯取代的环烯醛2，其热和光化学转化为甲酰基叠氮4，随后与三苯基膦发生开环反应。[11]（2,5）吡啶oph衍生物（S p，S）-14的HPLC分析和（R p，S）-14，表明这些非对映异构体在室温下会迅速发生自身异构化，并且与相应的[11]（2,5）环烷体系相比，它们的平面手性在热力学上不稳定。
• Macrocyclic Side-Chain Monomers for Photoinduced ATRP: Synthesis and Properties versus Long-Chain Linear Isomers
  作者：Stephanie M. Barbon、Manon Rolland、Athina Anastasaki、Nghia P. Truong、Morgan W. Schulze、Christopher M. Bates、Craig J. Hawker

  DOI：10.1021/acs.macromol.8b01509

  日期：2018.9.11

  The photoinduced atom transfer radical polymerization of traditionally challenging hydrophobic monomers (lauryl C12, stearyl C18, and docosyl C22-acrylate) and novel cyclic isomers (C12, C16, and C17) is reported. By the judicious selection of commercially available solvents and catalytic systems, polymers with a high degree of control over dispersity (Đ ≈ 1.1) and end-group fidelity were obtained

  据报道，传统上具有挑战性的疏水性单体（月桂基C 12，硬脂基C 18和二十二烷基C 22丙烯酸酯）和新型环状异构体（C 12，C 16和C 17）发生光诱导的原子转移自由基聚合。通过明智地选择市场上可买到的溶剂和催化体系，可以高度控制分散性的聚合物（Đ≈1.1）和端基保真度是在很宽的分子量范围内获得的。这种控制水平可提供独特的疏水性材料（无规，嵌段和均聚物）的访问权，这些特性由于烃侧链的异构形式（大环与线性）而具有明显的性能差异。
• Multi-compartment storage and delivery containers and delivery system for microencapsulated fragrances
  申请人：Troost Herman Erik

  公开号：US20060102656A1

  公开（公告）日：2006-05-18

  Described is a multiple (2-4)-compartment fluidic individually stable pre-storable composition storage and unstable mixture-forming and delivery container having separate compartments each communicating with a single mixing zone via an externally-located fluidic composition multiple delivery tube system juxtaposed with the outer surfaces of the compartment walls. These containers are well suited for storing and transporting compositions such as a cleaning agent composition, a personal care composition, an aqueous liquid detergent composition and/or a fabric softening composition and then promptly delivering the resulting unstable mixture to the desired location. The container has been advantageously found to deliver unstable mixtures which could include aqueous suspensions of microencapsulated fragrances or other ingredients.

  本发明涉及一种多（2-4）隔室流体单独稳定的可储存组合物储存容器和不稳定混合物形成和输送容器，其具有单独的隔室，每个隔室通过外部定位的流体组成物多重输送管系与隔室壁的外表面相邻，与单个混合区域相通。这些容器非常适合存储和运输诸如清洁剂组合物、个人护理组合物、水性液体洗涤剂组合物和/或柔顺剂组合物等组合物，然后迅速将产生的不稳定混合物输送到所需位置。有利地发现，该容器可输送包括微囊化香料或其他成分的水性悬浮液等不稳定混合物。