十七碳-2-基-1-醇 | 2833-98-9

• 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: 十七碳-2-基-1-醇
• 英文名称: heptadec-2-yl-1-ol
• 英文别名: heptadec-2-yn-1-ol；2-heptadecyn-1-ol；Heptadecin-(2)-ol-(1).
• CAS: 2833-98-9
• 化学式: C₁₇H₃₂O
• 分子量: 252.44
• InChiKey: DSKWEIAJLAZTHR-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  18
• 可旋转键数：
  12
• 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：

  十七碳-2-基-1-醇 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 生成 [(E)-heptadec-2-enyl]sulfanylbenzene
  参考文献：
  名称：

  Total synthesis of (+)-13,14-threo-densicomacin

  摘要：

  The tide compound was synthesized from propargyl alcohol and L-glutamic acid via a convergent approach using Sharpless asymmetric epoxidation and asymmetric dihydroxylation for the introduction of chiral centers and Pd-o-catalyzed coupling for construction of the carbon skeleton.

  DOI：

  10.1016/0040-4039(95)02007-c
• 作为产物：
  描述：

  十四烷基碘化物 在 六甲基磷酰三胺 、 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 十七碳-2-基-1-醇
  参考文献：
  名称：

  (Carboxyalkyl)benzyl Propargyl Ethers as Selective Inhibitors of Leukocyte-Type 12-Lipoxygenases

  摘要：

  A series of (carboxyalkyl)benzyl propargyl ethers was synthesized and tested as inhibitors of 12-lipoxygenase (12-LO) from porcine leukocyte cytosol. Optimum activity was displayed by 3-[4-[(2-tridecynyloxy)methyl]phenyl]propanoic acid. Altering the length of the alkyl side chain attached to the acetylenic group reduced activity. Changing the substitution pattern in the (carboxyalkyl)benzyl group from para to meta or ortho also reduced activity. Analogs in which the triple bond was replaced by a double bond or an allene displayed reduced activity, whereas fully saturated analogs were inactive. High concentrations (10 mu M) of the most potent acetylenic (carboxylalkyl)benzyl ethers did not inhibit human platelet 12-LO, human neutrophil 5-LO, rabbit reticulocyte 15-LO, or soybean 15-LO. Thus, this class of compounds represents the first example of isoform specific LO inhibitors.

  DOI：

  10.1021/jm9606047

文献信息

• Metal-mediated alkynediol cycloisomerization: first and second generation formal total syntheses of didemniserinolipid B
  作者：Shyamsundar Das、Boddeti Induvadana、C.V. Ramana

  DOI：10.1016/j.tet.2012.12.045

  日期：2013.2

  A formal total synthesis of didemniserinolipid B was developed by employing a regioselective metal-mediated 6-endo-dig alkynol-cycloisomerization reaction. Two routes for the synthesis of key Burke's intermediate have been developed. Our initial approach involved the introduction of a C17-alkynol followed by Pd-mediated cycloisomerization and then coupling with the serinol unit prior to the introduction

  通过使用区域选择性金属介导的6-内切-乙炔基-环异构化反应，开发了双美金刚烷脂B的正式全合成。已经开发了两种合成关键伯克中间体的途径。我们最初的方法涉及先引入C 17-炔醇，然后进行Pd介导的环异构化，然后再与丝氨醇单元偶联，然后通过选择性氧化1°-OH引入α，β-不饱和酯单元，然后引入两个-碳维蒂希（Wittig）认证。另外，第二代策略的特征是将丝氨醇与C 17偶联-炔醇，然后将炔烃加到环氧化物中，然后进行乙交酯保护的炔二醇单元的Au介导的环异构化。这种方法避免了数个后期保护-解除保护事件。
• Syntheses of two possible diastereoisomers of the epoxy lactone proposed for an annonaceous acetogenin, epoxyrollin A
  作者：Hiroyuki Konno、Hidefumi Makabe、Takayuki Oritani、Akira Tanaka

  DOI：10.1016/0040-4020(96)00477-2

  日期：1996.7

  Syntheses of two possible diastereoisomers (5S, 18′S, 19′R)- and (5S, 18′R, 19′S)-1 corresponding to the epoxy lactone that has been proposed for epoxyrollin A, a structural representative of biosynthetic precursors of tetrahydrofuran annonaceous acetogenins, are described. The 13C-NMR and tandem mass spectral data of the synthetic samples were not in accord with those recorded for natural epoxyrollin

  的两种可能的非对映体（5合成小号，18'小号，19' - [R和（5 - ）小号，18' - [R，19'小号已经提出的用于epoxyrollin A）-1对应于环氧内酯的结构代表描述了四氢呋喃非乙酰乙酸原素的生物合成前体。合成样品的13 C-NMR和串联质谱数据与天然环氧树胶A记录的数据不一致。因此，环氧树胶A的结构需要修改。
• A Fluorescent Probe for C24 Fatty Acids to Report the Deep Interior of Lipid Bilayers
  作者：Yuichi Umegawa、Michio Murata、Shiho Fukunaga、Tomokazu Yasuda

  DOI：10.1055/a-2210-1162

  日期：——

  fluctuation of lipid chains in the deep part of biomembranes, we aimed to develop a new fluorescent probe based on the well-known trans-parinaric acid (t-PA), but with a tetraene near the end of the C24 chain. The probe, tetracosa-16,18,20,22-tetraenoic acid (TCTEA), synthesized mainly by means of reported strategies, was found to better reflect the behavior of lipids in the deeper interior of bilayers than

  为了研究生物膜深层脂质链的交错和由此产生的波动，我们的目标是开发一种基于众所周知的反式石蜡油酸（t-PA）的新型荧光探针，但在末端附近有一个四烯。 C24链。主要通过报道的策略合成的探针 tetracosa-16,18,20,22-tetraenoic Acid (TCTEA) 被发现比 t-PA 更好地反映了双层更深内部的脂质行为。 TCTEA 可以作为研究超长链脂肪酸质膜动力学的有用探针，最近引起了与坏死性凋亡相关的广泛关注。
• Hyperextended amphiphiles. Bilayer formation from single-tailed compounds
  作者：F. M. Menger、Y. Yamasaki

  DOI：10.1021/ja00062a086

  日期：1993.5
• Grimmer,G.; Hildebrandt,A., Justus Liebigs Annalen der Chemie, 1965, vol. 685, p. 154 - 160
  作者：Grimmer,G.、Hildebrandt,A.

  DOI：——

  日期：——