rac-hexadecen-3-ol | 17642-49-8

• 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: rac-hexadecen-3-ol
• 英文别名: 1-hexadecen-3-ol；hexadec-1-ene；Hexadecen-(1)-ol-(3)；n-Hexadecen-1-ol-3；hexadec-1-en-3-ol
• CAS: 17642-49-8
• 化学式: C₁₆H₃₂O
• 分子量: 240.429
• InChiKey: ZCTCPJHTUFYTOR-UHFFFAOYSA-N

物化性质

• 沸点：
  168-171 °C(Press: 11 Torr)
• 密度：
  0.841±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  rac-hexadecen-3-ol 在 二氯二茂钛 、 重铬酸吡啶 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-(hydroxymethyl)-3-methylene-5-tridecyltetrahydrofuran-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of Polysubstituted Tetrahydrofurans by Radical Cyclization of Epoxides Using a Transition-Metal Radical Source. Application to the Total Synthesis of (±)-Methylenolactocin and (±)-Protolichesterinic Acid

  摘要：

  Radical cyclization reactions of substituted alpha-(prop-2-ynyloxy) epoxides using bis(cyclopentadienyl)-titanium(III) chloride as the radical source resulted in polysubstituted tetrahydrofurans. Titanium(III) species were prepared in situ from commercially available titanocene dichloride and zinc dust in tetrahydrofuran, Upon radical cyclization, 2-aryl epoxides 3a-e afforded only trans products 4a-e whereas the 2-alkyl epoxides 3f-h formed a mixture of isomeric products 4f-h in a ratio of 5:1. Some of the aryl tetrahydrofuran derivatives have already been used for the synthesis of bioactive furofuran lignans. 2-Pentyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4f) and 2-tridecyl-3-(hydroxymethyl)-4-methylenetetrahydrofuran (4g) have been transformed to two antitumor antibiotics (+/-)-methylenolactocin (1f) and (+/-)-protolichesterinic acid (1g), respectively, in good overall yield.

  DOI：

  10.1021/jo971526d
• 作为产物：
  描述：

  十六碳烯 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到rac-hexadecen-3-ol
  参考文献：
  名称：

  Synthesis of new ligands for targeting the S1P1 receptor

  摘要：

  Sphingosine-1-phosphate (S1P) influences various fundamental biological processes by interacting with a family of five G protein-coupled receptors (S1P(1-5)). FTY720, a sphingosine analogue, which was approved for treatment of relapsing forms of multiple sclerosis, is phosphorylated in vivo and acts as an agonist of four of the five S1P receptor subtypes. Starting from these lead structures we developed new agonists for the S1P(1) receptor. The biological activity was tested in vivo and promising ligands were fluorinated at different positions to identify candidates for positron emission tomography (PET) imaging after [F-18]-labelling. The radioligands shall enable the imaging of S1P(1) receptor expression in vivo and thus may serve as novel imaging markers of S1P-related diseases. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.014

文献信息

• Synthesis and Liquid Crystalline Properties of 5-Alkyl-1,4-dioxane-2-carboxylic­ Esters
  作者：Manfred Braun、Birgit Spieker、Antje Hahn、Volkmar Vill

  DOI：10.1055/s-2002-34390

  日期：——

  The first route to 5-alkyl substituted and purely trans-configurated 1,4-dioxanecarboxylic acids 3 is described. The mesogenic properties of the esters 17 and 20, which are derived from the acids 3 and esters 19 (prepared from the hemiacetal 8a), are studied and compared. An enantioselective route to 1,4-dioxanecarboxylic acid 3a is explained, and takes advantage of the stereoselective addition of the bromolithioalkene 11b to heptanal.

  描述了制备5-烷基取代和纯反式构型1,4-二氧杂环己烷羧酸3的第一条路线。研究并比较了源自酸3的酯17和源自半缩醛8a制备的酯19得到的酯20的液晶性质。阐述了制备1,4-二氧杂环己烷羧酸3a的手性选择性路线，并利用了溴锂烯烃11b对庚醛的立体选择性加成。
• Overman Rearrangement of Fluorinated Allylic Alcohols as a Key Step for the Synthesis of Glycyldecylamide (GDA) Mimics
  作者：Günter Haufe、Daniel Ramb

  DOI：10.1055/s-0033-1339665

  日期：——

  O verman rearrangements based on secondary 2-fluoroallylic alcohols were performed to synthesize fluorinated primary allylic amines for the first time. The vinylic fluorine atom dramatically slows down the reaction rate. Long alkyl chain fluorinated allylic amine, which is a mimic of a drug against schizophrenia, was further coupled with Boc-protected phenyl glycine, forming a Gly-Phe peptide mimic

  首次进行了基于仲 2-氟烯丙醇的 Overman 重排以合成氟化伯烯丙胺。乙烯基氟原子显着减慢反应速率。长烷基链氟化烯丙胺是一种抗精神分裂症药物的模拟物，进一步与 Boc 保护的苯基甘氨酸偶联，形成 Gly-Phe 肽模拟物。
• 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。
• [3,3]-Sigmatropic Rearrangements of Fluorinated Allyl (Thio)cyanates – A Tool for the Synthesis of Fluorinated (Thio)ureas
  作者：Daniel C. Ramb、Lisa Kost、Günter Haufe

  DOI：10.2533/chimia.2014.436

  日期：——

  sigmatropic rearrangement to fluorinated allyl isocyanates. Without isolation the latter delivered fluorinated ureas by addition of amines. The thiocyanate to isothiocyanate rearrangements started from the same fluorinated allylic alcohols, which were first converted to mesylates. Heating in THF with potassium thiocyanate led to fluorinated allyl isothiocyanates, via [3,3]-sigmatropic rearrangement of intermediate

  提出了基于2-氟代烯丙基醇的第一（硫代）氰酸酯到异（硫代）氰酸酯的重排。通过用三氯乙酰基异氰酸酯处理，将长链2-氟代烯丙基醇转化为相应的N-未取代的氨基甲酸酯。在三乙胺的存在下使用三氟乙酸酐进行脱水，形成中间体烯丙基氰酸酯，该中间体立即进行σ重排，生成氟化的烯丙基异氰酸酯。在不分离的情况下，后者通过添加胺来递送氟化脲。硫氰酸酯向异硫氰酸酯的重排是从相同的氟化烯丙基醇开始的，首先将其转化为甲磺酸酯。在THF中与硫氰酸钾一起加热，经由中间体硫氰酸烯丙酯的[3,3]-σ重排而导致氟化的异硫氰酸烯丙酯。
• New approach to α-pentafluorosulfanyl-substituted carboxylic acid derivatives via Ireland-Claisen rearrangements
  作者：Anna-Lena Dreier、Andrej V. Matsnev、Joseph S. Thrasher、Günter Haufe

  DOI：10.1016/j.jfluchem.2014.05.006

  日期：2014.11

  synthesized via Ireland-Claisen rearrangements. The formation of intermediate (E)- and (Z)-enolates as the key-step was confirmed by NMR spectroscopy, which also indicated that only the (Z)-enolates rearrange, while the (E)-enolates are stable under the reaction conditions and hydrolyze back to the starting allylic esters during aqueous workup. As a consequence an incomplete rearrangement of the starting

  向一个新的合成策略α-五氟硫烷基羧基的化合物被开发。从烯丙基酯，其是从氟化或无氟烯丙醇制备酯化pentafluorosulfanylacetyl氯化物，范围的起始的反式-型γ，δ不饱和α-五氟硫烷基羧酸合成经由爱尔兰-克莱森重排。中间体（形成ë） -和（Ž）-enolates作为关键步骤用NMR光谱，这也表明，只有第（确认Ž）-enolates重新排列，而（Ë）-烯酸酯在反应条件下是稳定的，并且在水性后处理过程中水解回起始的烯丙基酯。结果，观察到起始酯的不完全重排。将形成的酸转化成相应的甲酯使得更容易分离所需的含五氟硫烷基的产物。