6-octadecyn-1-ol | 2861-50-9

• 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: 6-octadecyn-1-ol
• 英文别名: 6-Octadecinol；octadec-6-yn-1-ol；Taririnalkohol；Octadec-6-in-1-ol
• CAS: 2861-50-9
• 化学式: C₁₈H₃₄O
• 分子量: 266.467
• InChiKey: OONKNWFYBDPRIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  6-octadecyn-1-ol 在 喹啉 、 重铬酸吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 十八碳6烯酸
  参考文献：
  名称：

  2-甲氧基化FA对耐甲氧西林金黄色葡萄球菌（CIMRSA）和大肠杆菌的临床分离株显示出异常的抗菌活性。

  摘要：

  在7-8中合成了天然存在的（6 Z）-（±）-2-甲氧基-6-十六碳烯酸（1）和（6 Z）-（±）-2-甲氧基-6十八碳烯酸（2）通过使用乙炔偶联方法，可分别获得38％和13％的总收率，这使得双键的顺式立体化学达到100％成为可能。乙炔类似物（±）-2--2-甲氧基-6-十六碳烯酸（3）和（±）-2-甲氧基-6十八碳烯酸（4）也通过6-7步骤与48和48总产量分别为16％。酸的抗菌活性1 - 4已针对耐甲氧西林金黄色葡萄球菌（ClMRSA）和大肠杆菌的临床分离株进行了检测。在一系列化合物中，酸4是对CIMRSA活性最高的杀菌剂，IC 50s（半数最大抑制浓度）在17至37μg / mL之间，与6十八碳烯酸完全相反，后者完全没有杀菌作用。另一方面，酸1和3是仅有的对大肠杆菌具有抗菌活性的酸，但酸1的最佳候选者是IC 50为21μg/ mL的最佳人选。酸的临界胶束浓度（CMCs）1–还确定了4

  DOI：

  10.1007/s11745-017-4262-1
• 作为产物：
  描述：

  塔日酸 在 硫酸 、 水 、 sodium 、 正丁醇 作用下， 生成 6-octadecyn-1-ol
  参考文献：
  名称：

  Elevation of plasma fatty acids by ten-hour intralipid infusion has no effect on basal or glucose-stimulated insulin secretion in normal man

  摘要：

  There is controversy over the effect of free fatty acids (FFAs) on insulin secretion. Previous studies have shown opposite effects of short- and long-term exposure to elevated concentrations of FFAs. We studied 8 normal subjects (mean age, 30 years; mean body mass index, 23.4 kg/m(2)) on 2 occasions. Each had a 10-hour overnight infusion of Intralipid 20% (Pharmacia, Milton Keynes, UK) with simultaneous infusion of heparin (0.4 U/kg body weight/min) or a control infusion of saline (150 mmol/L). Insulin secretion was assessed immediately after completion of the 10-hour infusion by an intravenous glucose tolerance test. Results were analyzed using paired t tests. Intralipid infusion caused an increase in plasma FFAs of more than 9-fold (P <.01), with a simultaneous increase in glycerol (P <.01) and hydroxybutyrate (P <.01). There was no difference in blood glucose concentrations during the infusion or intravenous glucose tolerance test. Similarly, insulin secretion was not significantly different during Intralipid infusion or in the intravenous glucose tolerance test (peak insulin achieved in glucose tolerance test, P =.51; total insulin secretion during intravenous glucose tolerance test, P =.27). In conclusion, after increasing plasma FFA concentrations over g-fold during a 10-hour infusion of Intralipid and heparin, we found no difference in basal or glucose-stimulated insulin secretion. Copyright (C) 2000 by W.B. Saunders Company.

  DOI：

  10.1016/s0026-0495(00)80007-4

文献信息

• Preparation of functionalized alkynes having internal triple bonds
  申请人：Kenkel Research Corporation

  公开号：US05093536A1

  公开（公告）日：1992-03-03

  Functional internal alkynes are conveniently and economically prepared by dehydrohalogenating a dibromide with an alkali metal hydroxide in the presence of a phase transfer catalyst.

  通过在相转移催化剂的存在下，使用碱金属氢氧化物去卤化二溴化物，可以方便、经济地制备功能性内炔。
• Gold‐Zinc Cooperative Catalysis for Seven‐<i>exo</i>‐<i>dig</i> Hydrocarboxylation of Internal Alkynes
  作者：Miyu Sato、Vishal Kumar Rawat、Kosuke Higashida、Masaya Sawamura

  DOI：10.1002/chem.202301917

  日期：2023.10.9

  Seven‐exo‐dig hydrocarboxylation of nonactivated internal alkynes with conformationally flexible linker chains was achieved with cooperative gold‐zinc catalysts composed of an imidazo[1,5‐a]pyridinylidene ligand including a bipyridine coordination site at the C5 position. A proximity effect of the gold and zinc sites was essential for their high catalytic activity, in which the internal alkyne activated by the cationic gold species was attacked by the carboxylic acid deprotonated by the basic zinc site. Using a gold(I)‐complex with a bulky aromatic N‐substituent, 2,6‐dibenzhydryl‐4‐methylphenyl group, for the NHC ligand facilitated seven‐membered ring formation while minimizing intermolecular hydrocarboxylation as an undesired side reaction. The reaction mechanism was investigated by quantum chemical calculations.

  摘要利用由咪唑并[1,5-a]吡啶亚基配体（包括位于 C5 位的双吡啶配位位点）组成的金锌协同催化剂，实现了具有灵活构象连接链的非活化内部炔烃的七外羰基化。金和锌配位位点的邻近效应对它们的高催化活性至关重要，其中被阳离子金激活的内部炔烃被碱性锌配位位点去质子化的羧酸攻击。使用带有笨重芳香 N-取代基（2,6-二苯甲酰基-4-甲基苯基）的金（I）-络合物作为 NHC 配体，有助于形成七元环，同时最大程度地减少分子间羧酸化这一不希望发生的副反应。量子化学计算对反应机理进行了研究。
• Metalation reactions. III. Metalation of octadecynols and octadecynyl methyl ethers
  作者：Joseph Klein、E. Gurfinkel

  DOI：10.1021/jo01264a044

  日期：1969.12
• US4440940A
  申请人：——

  公开号：US4440940A

  公开（公告）日：1984-04-03
• US5093536A
  申请人：——

  公开号：US5093536A

  公开（公告）日：1992-03-03