4-decyn-1-ol | 69222-06-6

• 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: 4-decyn-1-ol
• 英文别名: Dec-4-YN-1-OL
• CAS: 69222-06-6
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: PBYDSMYJBSYNTG-UHFFFAOYSA-N

物化性质

• 熔点：
  1.9°C (estimate)
• 沸点：
  247.64°C (rough estimate)
• 密度：
  0.8568 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  4-decyn-1-ol 在 咪唑 、 喹啉 、 5% Pd-CaCO3 、 氢气 、 碘 、 三苯基膦 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.5h， 生成 (4Z)-1-iodo-4-decene
  参考文献：
  名称：

  An Improved and Convenient New Synthesis of the Pheromone Components of the Tomato Leafminer Tuta absoluta

  摘要：

  A convenient new synthesis of the two pheromone components of the tomato pest Tuta absoluta in high overall yields and high stereoselectivity (30% yield, E,Z,Z 97% for the major compound and 23% yield, E,Z 99% for the minor component) is reported. The approaches compare favorably with others previously described.

  DOI：

  10.1055/s-0034-1379977
• 作为产物：
  描述：

  1-(tert-butyldimethylsilyloxy)-4-pentyne 在 N,N-二甲基丙烯基脲 、 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 30.0h， 生成 4-decyn-1-ol
  参考文献：
  名称：

  Ligand-Controlled, Tunable Silver-Catalyzed C–H Amination

  摘要：

  The development of readily tunable and regioselective C-H functionalization reactions that operate solely through catalyst control remains a challenge in modern organic synthesis. Herein, we report that simple silver catalysts supported by common nitrogenated ligands can be used to tune a nitrene transfer reaction between two different types of C-H bonds. The results reported herein represent the first example of ligand-controlled and site-selective silver-promoted C-H amination.

  DOI：

  10.1021/ja5094309

文献信息

• The Mechanism of Gold(I)-Catalyzed Hydroalkoxylation of Alkynes: An Extensive Experimental Study
  作者：Alexander Zhdanko、Martin E. Maier

  DOI：10.1002/chem.201303795

  日期：2014.2.10

  An extensive experimental study of the mechanism of gold(I)‐catalyzed hydroalkoxylation of internal alkynes has been conducted by using NMR spectroscopy. This study was focused on the organogold intermediates, observations of actual catalytic intermediates in situ, and the reaction kinetics that are involved in this reaction. Based on the experimental results, a complete mechanistic picture was established

  使用NMR光谱对金（I）催化的内部炔烃加氢烷氧基化机理进行了广泛的实验研究。这项研究的重点是有机金中间体，原位实际催化中间体的观察以及该反应涉及的反应动力学。根据实验结果，建立了完整的机理图，包括解释了稀有物种的作用的循环和非循环过程。我们已经表明，内部炔烃的金催化加氢烷氧基化反应只需要一个金原子就可以进行催化循环，这证明了有关协同金催化作用的最新假设。
• Chemoselective Biohydrogenation of Alkenes in the Presence of Alkynes for the Homologation of 2‐Alkynals/3‐Alkyn‐2‐ones into 4‐Alkynals/Alkynols
  作者：Danilo Colombo、Elisabetta Brenna、Francesco G. Gatti、Maria Chiara Ghezzi、Daniela Monti、Fabio Parmeggiani、Francesca Tentori

  DOI：10.1002/adsc.201900177

  日期：——

  activated alkene bonds by ene‐reductases (ERs) is completely chemoselective, because of the mechanism of the reaction. Thus, we investigated the use of ERs belonging to the Old Yellow Enzyme family for the reduction of α,β‐unsaturated aldehydes with a conjugated C≡C triple bond at the γ position. This reaction was exploited as the key step for the development of an effective homologation route to convert

  在炔烃的存在下烯烃的化学选择氢化是用传统化学方法实现的非常具有挑战性的转化。开发一种有效的方法来进行这种转化将丰富有机化学家可用的工具包，以开发有用的合成路线，并创建新的结构基序。由于反应机理，烯还原酶（ER）还原活化的烯烃键是完全化学选择性的。因此，我们研究了使用旧黄色酶家族的ER来还原在γ位上具有共轭C≡C三键的α，β-不饱和醛。
• A ring opening reaction of oxetanes with lithium acetylides promoted by boron trifluoride etherate
  作者：Masahiko Yamaguchi、Yukio Nobayashi、Ichiro Hirao

  DOI：10.1016/s0040-4020(01)98801-5

  日期：——

  Several substituted oxetanes were treated with lithium acetylides in the presence of boron trifluoride etherate to give f-hydroxyacetylenes. The reaction conditions were varied and several synthetic features of the present reaction were revealed.

  在三氟化硼醚化物的存在下，用乙炔锂处理几种取代的氧杂环丁烷，得到f-羟基乙炔。反应条件是变化的，并且揭示了本反应的一些合成特征。
• Rhodium-Catalyzed Arylative Cyclization for the Enantioselective Synthesis of (Trifluoromethyl)cyclobutanols
  作者：Thomas Johnson、Ken-Loon Choo、Mark Lautens

  DOI：10.1002/chem.201404896

  日期：2014.10.27

  A rhodium‐catalyzed cyclization of 1‐(trifluoromethyl)‐4‐alkyn‐1‐ones with arylboronic acids is described to yield a novel class of small rings: (trifluoromethyl)cyclobutanols bearing an exocyclic double bond. The use of a rhodium/chiral diene complex allowed the reaction to proceed under mild conditions, often with high enantioselectivity. An X‐ray crystal structure was obtained confirming the formation

  铑与芳基硼酸催化的1-（三氟甲基）-4-炔基-1-酮的环化反应可产生一类新的小环：带有三环外键的（三氟甲基）环丁醇。铑/手性二烯配合物的使用允许反应在温和的条件下进行，通常具有高对映选择性。获得了X射线晶体结构，证实了四元环产物的形成。
• Silver-Catalyzed Enantioselective Propargylic C–H Bond Amination through Rational Ligand Design
  作者：Minsoo Ju、Emily E. Zerull、Jessica M. Roberts、Minxue Huang、Ilia A. Guzei、Jennifer M. Schomaker

  DOI：10.1021/jacs.0c05726

  日期：2020.7.29

  precursors from abundant C-H bonds. Herein, we report a regio- and enantioselective synthesis of -alkynyl -aminoalcohols via a silver-catalyzed propargylic C-H amination. The protocol was enabled by a new bis(oxazoline) (BOX) ligand designed via a rapid structure-activity relationship (SAR) analysis. The method utilizes accessible carbamate esters bearing -propargylic C-H bonds and furnishes versatile products

  通过氮宾转移 (NT) 进行的不对称 CH 胺化是从丰富的 CH 键制备对映体富集的胺前体的强大工具。在此，我们报道了通过银催化的炔丙基CH胺化，区域选择性和对映选择性合成γ-炔基γ-氨基醇。该方案是通过快速构效关系（SAR）分析设计的新型双（恶唑啉）（BOX）配体实现的。该方法利用带有 γ-炔丙基 CH 键的易得氨基甲酸酯，并提供具有良好收率和优异对映选择性 (90-99% ee) 的多功能产品。假定的银氮烯被认为在 CH 胺化事件期间经历对映决定的氢原子转移。密度泛函理论计算揭示了 HAT 步骤中对映选择性的起源。