2,2-二甲基-5-己烯-1-醇 | 56068-50-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2,2-二甲基-5-己烯-1-醇
• 英文名称: 2,2-dimethylhex-5-en-1-ol
• 英文别名: 2,2-dimethyl-5-hexen-1-ol
• CAS: 56068-50-9
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: WIYYDFSDWKBPIX-UHFFFAOYSA-N

物化性质

• 沸点：
  175℃
• 密度：
  0.836
• 闪点：
  65℃

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  2,2-二甲基-5-己烯-1-醇 在 五氯化磷 、 magnesium 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 1,1,3-三甲基环戊烷
  参考文献：
  名称：

  Mechanism of Reaction of Geminal Dihalides with Magnesium. Evidence for the Formation of Carbenes from Radical Precursors. The Similarity in Reactions of Geminal Dihalides with Magnesium and LiAlH4

  摘要：

  Two geminal dihalides, 6,6-dichloro-5,5-dimethyl-1-hexene (2a) and 6,6-diiodo-5,5-dimethyl-1-hexene (2b) were allowed to react with Rieke activated magnesium (Mg*) in THF at 25 degrees C. Both radical and carbene intermediates were identified by product analyses, by radical trapping experiments using DCPH and THF-d(8), and by selective experiments in which isolated intermediates were shown to form the predicted products. Although carbene products predominated over radical products when the dichloride was allowed to react with Mg*, radical products predominated when the diiodide was allowed to react with Mg*. Evidence is presented that indicates that the carbene intermediate arises from a radical precursor. A mechanistic scheme (Scheme 5) is presented that is consistent with all of the observed data. A comparison of the reactions of 2b with Mg* and 2b with LiAlH4 shows that most of the products are common in both reactions thereby providing further evidence for LiAlH4 as a one-electron donor, as is the known behavior of Mg*.

  DOI：

  10.1021/jo00100a024
• 作为产物：
  描述：

  methyl 2,2-dimethyl-5-hexenoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2,2-二甲基-5-己烯-1-醇
  参考文献：
  名称：

  调节烷氧基自由基从环化到 1,2-甲硅烷基转移的反应性：β-取代环醇的立体选择性合成

  摘要：

  在此，我们报告了一种非对映选择性构建β-取代的环戊醇和环丁醇的激进策略。反应的成功归因于在烷氧基环化为烯烃时有利的自由基 1,2-甲硅烷基转移。该反应显示出广泛的底物范围和广泛的官能团耐受性。该方法的合成潜力在克级反应和各种螺环化合物的简便合成中得到了证明。

  DOI：

  10.1021/acs.orglett.2c00428

文献信息

• Rhodium-Catalyzed Cyclization of <i>O</i> ,ω-Unsaturated Alkoxyamines: Formation of Oxygen-Containing Heterocycles
  作者：Julien Escudero、Véronique Bellosta、Janine Cossy

  DOI：10.1002/anie.201710895

  日期：2018.1.8

  O,ω‐Unsaturated N‐tosyl alkoxyamines undergo unexpected RhIII‐catalyzed intramolecular cyclization by oxyamination to produce oxygen‐containing heterocycles. Mechanistic studies show that an aziridine intermediate seems to be responsible for the formation of the heterocycles, possibly via a RhV species.

  O，ω-不饱和N-甲苯磺酰基烷氧基胺通过氧化作用经历了Rh Rh催化的不可思议的Rh III分子内环化反应，生成了含氧杂环。机理研究表明，氮丙啶中间体似乎是可能通过Rh V物种造成了杂环的形成。
• HCV NS3 protease inhibitors
  申请人：Holloway Katharine M.

  公开号：US20070027071A1

  公开（公告）日：2007-02-01

  The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.

  本发明涉及一种公式（I）的大环化合物，该化合物可用作乙型肝炎病毒（HCV）NS3蛋白酶的抑制剂，其合成以及用于治疗或预防HCV感染的用途。
• MASKED CARBOXYLATE NEOPENTYL SULFONYL ESTER CYCLIZATION RELEASE PRODRUGS OF ACAMPROSATE, COMPOSITIONS THEREOF, AND METHODS OF USE
  申请人：Jandeleit Bernd

  公开号：US20090069419A1

  公开（公告）日：2009-03-12

  Masked carboxylate neopentyl sulfonyl ester prodrugs of acamprosate, pharmaceutical compositions comprising such prodrugs, and methods of using such prodrugs and compositions thereof for treating diseases are disclosed. In particular, acamprosate prodrugs exhibiting enhanced oral bioavailability and methods of using acamprosate prodrugs to treat neurodegenerative disorders, psychotic disorders, mood disorders, anxiety disorders, somatoform disorders, movement disorders, substance abuse disorders, binge eating disorder, cortical spreading depression related disorders, tinnitus, sleeping disorders, multiple sclerosis, and pain are disclosed.

  掩蔽羧酸新戊磺酰酯丙戊酸酯前药，包含此类前药的药物组合物，以及使用此类前药和组合物治疗疾病的方法被披露。具体来说，披露了表现出增强口服生物利用度的丙戊酸酯前药和使用丙戊酸酯前药治疗神经退行性疾病、精神疾病、情绪障碍、焦虑障碍、躯体形式障碍、运动障碍、物质滥用障碍、暴饮暴食障碍、皮层扩散性抑郁相关障碍、耳鸣、睡眠障碍、多发性硬化症和疼痛的方法。
• Radical cascade cyclizations and platinum(II)-catalyzed cycloisomerizations of ynamides
  作者：Frédéric Marion、Julien Coulomb、Aurore Servais、Christine Courillon、Louis Fensterbank、Max Malacria

  DOI：10.1016/j.tet.2005.11.092

  日期：2006.4

  Ynamides are tested as new partners in radical and organometallic transformations. A radical cascade involving a 5-exo-dig cyclization followed by a 6-endo-trig radical trapping transforms ynamides into hetero-polycyclic compounds such as isoindoles, isoindolinones and pyrido-isoindolones. Various ene–tosylynamides react with platinum(II) chloride and lead to bicyclic nitrogenated heterocycles. This

  氰化物作为自由基和有机金属转变的新伙伴进行了测试。涉及5- exo - dig环化和6- endo - trig自由基捕获的自由基级联反应将酰胺转化为异多环化合物，例如异吲哚，异吲哚满酮和吡啶基-异吲哚满酮。各种烯基-甲苯磺酰基酰胺与氯化铂（II）反应并生成双环含氮杂环。这种空前的，易于操作的过程可以与一环转化中的中间体环状甲苯磺酰胺的水解反应结合在一起，从而提供环丁酮。
• Platinum Dichloride-Catalyzed Cycloisomerization of Ene-ynamides
  作者：Frédéric Marion、Julien Coulomb、Christine Courillon、Louis Fensterbank、Max Malacria

  DOI：10.1021/ol049530g

  日期：2004.4.1

  [reaction: see text] Various ene-tosylynamides react with platinum(II) chloride and lead to bicyclic nitrogenated heterocycles. This unprecedented and easily operated process can be coupled with a hydrolysis of the intermediate cyclic tosylenamides in a one-pot transformation, which provides cyclobutanones.

  [反应：见正文]各种烯基甲苯磺酰胺与氯化铂（II）反应并生成双环含氮杂环。这种空前的，易于操作的过程可以与一环转化中的中间体环状甲苯磺酰胺的水解反应结合在一起，从而提供环丁酮。