5-ethynylnonan-5-ol | 7737-41-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-ethynylnonan-5-ol
• 英文别名: 5-ethynyl-5-nonanol；3-butyl-1-heptyn-3-ol
• CAS: 7737-41-9
• 化学式: C₁₁H₂₀O
• 分子量: 168.279
• InChiKey: BCNFZPFDVPQUEH-UHFFFAOYSA-N

物化性质

• 沸点：
  200-205 °C
• 密度：
  0.8552 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  5-ethynylnonan-5-ol 在 copper(l) chloride 正丙胺 、 盐酸羟胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 12.5h， 生成 1,1-dibutyl-5-(triisopropylsilyl)penta-2,4-diynyl methyl carbonate
  参考文献：
  名称：

  1,3-Diethynylallenes: Carbon-Rich Modules for Three-Dimensional Acetylenic Scaffolding

  摘要：

  Regioselective Pd-0-catalyzed cross-coupling of substrates, which bear bispropargylic leaving groups with silyl-protected alkynes, has provided access to a variety of 1.3-diethynylailenes, a new family of modules for three-dimensional acetylenic scaffolding. In enantiomerically pure form, these C-rich building blocks could provide access - by oxidative oligomerization - to a fascinating new class of helical oligomers and polymers with all-carbon backbones (Fig. 2). In the first of two routes. a bispropargylic epoxide underwent ring opening during S(N)2'-type cross-coupling. and the resulting alkoxide was silyl-protected, providing 1,3-diethynylailenes (+/-)-8, (+/-)-12 (Scheme 3), and (+/-)-15 (Scheme 5). A more general approach involved bispropargylic carbonates or esters as substrates (Scheme 6-8), and this route was applied to the preparation of a series of 13-diethyrrylallenes to investigate how their overall stability against undesirable [2 + 2] cycloaddition is affected by the nature of the substituents at the allene moiety. The investigation showed that the 1,3-diethynylallene chromophore is stable against [2 + 2] cycloaddition only when protected by steric bulk and when additional relectron delocalization is avoided. The regioselectivity of the cross-coupling to the bispropargylic substrates is entirely controlled by steric factors: attack occurs at the alkyne moiety bearing the smaller substituent (Schemes 9 and 10). Oxidative Hay coupling of the terminally mono-deprotected 1.3-diethynylallene (+/-)-49 afforded the first dimer 50, probably as a mixture of two diastereoisomers (Scheme 12). Attempts to prepare a silyl-protected tetraethynylallene by the new methodology failed (Scheme 13). Control experiments (Schemes 14 - 16) showed that the Pd-0-catalyzed cross-coupling to butadiyne moieties in the synthesis of this still-elusive chromophore requires forcing conditions under which rapid [2 + 2] cycloaddition of the initial product cannot be avoided.

  DOI：

  10.1002/1522-2675(200210)85:10<3052::aid-hlca3052>3.0.co;2-4
• 作为产物：
  描述：

  5-壬酮 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 5-ethynylnonan-5-ol
  参考文献：
  名称：

  通过金催化的不对称级联反应合并吲哚的合成和对映选择性官能化

  摘要：

  一次：在手性阳离子Au I配合物的帮助下，吲哚核同时合成和对映选择性官能化。通过级联工艺以高度对映选择性的方式获得了一系列乙烯基恶嗪基[4,3- a ]吲哚（参见方案；L =手性二膦）。

  DOI：

  10.1002/anie.201304619

文献信息

• AMINE DERIVATIVE COMPOUNDS FOR TREATING OPHTHALMIC DISEASES AND DISORDERS
  申请人：Acucela, Inc.

  公开号：US20160193181A1

  公开（公告）日：2016-07-07

  Provided are amine derivative compounds, pharmaceutical compositions thereof, and methods of treating ophthalmic diseases and disorders, such as age-related macular degeneration and Stargardt's Disease, using said compounds and compositions.

  提供的是胺衍生物化合物、其药物组合物，以及使用所述化合物和组合物治疗眼科疾病和障碍的方法，例如年龄相关的黄斑变性和斯达格特病。
• Facile Synthesis of Halogenated Spiroketals via a Tandem Iodocyclization
  作者：Jia Wang、Hai-Tao Zhu、Ying-Xiu Li、Li-Jing Wang、Yi-Feng Qiu、Zi-Hang Qiu、Mei-jin Zhong、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/ol500741a

  日期：2014.4.18

  A strategy for the synthesis of spiroketal compounds through a tandem iodocyclization of 1-(2-ethynylphenyl)-4-hydroxybut-2-yn-1-one derivatives is presented. This reaction could proceed under very mild conditions in a short time and avoid the use of expensive and toxic metal catalysts. Moreover, the resulting halides can be further exploited by subsequent palladium-catalyzed coupling reactions, which

  提出了通过1-（2-乙炔基苯基）-4-羟基丁-2-yn-1-one衍生物的串联碘代环合合成螺环化合物的策略。该反应可以在非常温和的条件下在短时间内进行，并且避免使用昂贵且有毒的金属催化剂。此外，所得的卤化物可通过随后的钯催化的偶联反应进一步开发，该偶联反应可作为构建其他有价值化合物的重要中间体。
• Ligand‐Controlled Palladium‐Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α‐Methylene‐β‐Lactones
  作者：Yao Ge、Fei Ye、Jiawang Liu、Ji Yang、Anke Spannenberg、Haijun Jiao、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.202006550

  日期：2020.11.23

  The first general and regioselective Pd‐catalyzed cyclocarbonylation to give α‐methylene‐β‐lactones is reported. Key to the success for this process is the use of a specific sterically demanding phosphine ligand based on N‐arylated imidazole (L11) in the presence of Pd(MeCN)2Cl2 as pre‐catalyst. A variety of easily available alkynols provide under additive‐free conditions the corresponding α‐methylene‐β‐lactones

  报道了第一个普通的和区域选择性的Pd催化的环羰基化反应，生成α-亚甲基-β-内酯。该工艺成功的关键是在Pd（MeCN）2 Cl 2作为预催化剂的情况下，使用基于N-芳基化咪唑（L11）的特定空间要求的膦配体。在无添加剂条件下，各种容易获得的炔醇以中等至良好的产率提供相应的α-亚甲基-β-内酯，具有出色的区域选择性和非对映选择性。这种新方法的适用性通过包括天然产物在内的生物活性分子的直接羰基化得以展示。
• Synthesis of Functionalized Polycyclic Compounds: Rhodium(I)-Catalyzed Intramolecular Cycloaddition of Yne and Ene Vinylidenecyclopropanes
  作者：Bei-Li Lu、Min Shi

  DOI：10.1002/anie.201105292

  日期：2011.12.9

  Three ring circus: The title reaction can efficiently provide functionalized polycyclic compounds containing cyclobutene (see scheme; PG=protecting group) or aza‐cyclooctene moieties in a highly regio‐ and diastereoselective manner with moderate to good yields under mild reaction conditions. The scope and limitations are disclosed and plausible reaction mechanisms are discussed.

  三环杂技团：标题反应可以在温和的反应条件下，以高区域和非对映选择性的方式，高效地提供含有环丁烯（见方案； PG =保护基）或氮杂-环辛烯部分的官能化多环化合物。公开了范围和限制，并讨论了可能的反应机理。
• [EN] SUBSTITUTED HETEROCYCLIC COMPOUNDS FOR DISEASE TREATMENT<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES SUBSTITUÉS POUR LE TRAITEMENT D'UNE MALADIE
  申请人：ACUCELA INC

  公开号：WO2013109991A1

  公开（公告）日：2013-07-25

  The present invention relates generally to compositions and methods for treating neurodegenerative diseases and disorders, particularly ophthalmic diseases and disorders. Provided herein are substituted heterocyclic amine derivative compound and pharmaceutical compositions comprising these compounds. The subject compositions are useful for treating and preventing ophthalmic diseases and disorders, including age-related macular degeneration (AMD) and Stargardt's Disease.

  本发明一般涉及治疗神经退行性疾病和紊乱的组合物和方法，特别是眼科疾病和紊乱。本文提供了替代杂环胺衍生物化合物和包含这些化合物的药物组合物。所述组合物对治疗和预防眼科疾病和紊乱，包括年龄相关性黄斑变性（AMD）和Stargardt病具有用处。