trans-3-decen-5-yn-2-one | 63922-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-3-decen-5-yn-2-one
• 英文别名: (E)-dec-3-en-5-yn-2-one；dec-3t-en-5-yn-2-one；Dec-3t-en-5-in-2-on
• CAS: 63922-98-5
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: XLYBQHKPXGMSML-CMDGGOBGSA-N

物化性质

• 沸点：
  232.3±23.0 °C(Predicted)
• 密度：
  0.896±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-3-decen-5-yn-2-one 在 甲醇 、 铂 作用下， 生成 2-癸酮
  参考文献：
  名称：

  Jutz, Chemische Berichte, 1958, vol. 91, p. 1867,1876

  摘要：

  DOI：
• 作为产物：
  描述：

  正戊醛 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.58h， 生成 trans-3-decen-5-yn-2-one
  参考文献：
  名称：

  Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins

  摘要：

  A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.

  DOI：

  10.1021/ol502551u

文献信息

• A convenient method for the preparation of α-vinylfurans by phosphine-initiated reactions of various substituted enynes bearing a carbonyl group with aldehydes
  作者：Hirofumi Kuroda、Emi Hanaki、Hironori Izawa、Michiko Kano、Hiromi Itahashi

  DOI：10.1016/j.tet.2003.12.034

  日期：2004.2

  at the ene end in the presence of various aldehydes, in moderate to high yields. The reaction may consist of 1,6-addition of phosphine to the enynes, ring closure, and Wittig reaction between the ylid resulting from cyclization and an aldehyde. Thus, various aldehydes were able to be used in the reaction. The reaction was influenced greatly by the substituents at the acetylene position (R1) and the α-position

  α-乙烯基呋喃是通过在各种醛存在下，通过膦引发的烯键末端带有羰基的各种烯炔的膦化引发的环化反应而制得的，产率中等至高。该反应可以包括将1，6-膦添加到烯炔上，闭环，以及由环化产生的基团和醛之间的Wittig反应。因此，各种醛能够用于反应中。该反应受到乙炔位置（R 1）和羰基的α位置（R 3）上的取代基的影响很大。
• Regio- and Stereoselective Synthesis of Vinylallenes by 1,5-(SN′′)-Substitution of Enyne Acetates and Oxiranes with Organocuprates
  作者：Martin Purpura、Norbert Krause

  DOI：10.1002/(sici)1099-0690(199901)1999:1<267::aid-ejoc267>3.0.co;2-v

  日期：1999.1

  substitution patterns react with organocuprates regioselectively under 1,5-(SN2′′)-substitution to provide vinylallenes 11 and 12. With lithium dimethylcuprate, reduced vinylallenes originating from a (formal) transfer of a hydride ion to the substrate are formed in some cases. The products are usually obtained as mixtures of (E/Z)isomers; however, pure (E)-vinylallenes are formed occasionally. The 1,5-substitutions

  具有不同取代模式的烯炔乙酸酯 2、4、6 和 8 以及烯炔环氧乙烷 10 在 1,5-(SN2'')-取代下与有机铜酸盐区域选择性地反应以提供乙烯基丙二烯 11 和 12。使用二甲基铜酸锂，还原在某些情况下，会形成源自氢化物离子（正式）转移到基材上的乙烯基丙二烯。产品通常以 (E/Z) 异构体的混合物形式获得；然而，偶尔会形成纯 (E)-乙烯基丙二烯。1,5-取代也可以用催化量的铜试剂进行。手性醋酸烯炔(S)-2a与tBu2CuLi·LiCN的反应对映选择性地进行，使这种转化构成了远程立体控制的新案例。
• A convenient method for the preparation of furans by the phosphine-initiated reactions of enynes bearing a carbonyl group
  作者：Hirofumi Kuroda、Emi Hanaki、Mayumi Kawakami

  DOI：10.1016/s0040-4039(99)00601-2

  日期：1999.5

  α-position were obtained by phosphine-initiated cyclization of enynes bearing a carbonyl group at the ene-side in the presence of aldehyde in high yield. The reaction may involve the 1,6-addition of phosphine toward the enynes, ring closure, and Wittig reaction of the ylid resulted from the cyclization with aldehyde.

  通过在醛存在下在醛存在下以膦开始的在烯侧带有羰基的烯炔的膦引发的环化反应，可以得到在α-位具有双键的呋喃。该反应可能涉及将膦1,6-加成至烯炔，闭环和由醛环化导致的碘的Wittig反应。
• Arndt, Silke; Handke, Gabriele; Krause, Norbert, Chemische Berichte, 1993, vol. 126, # 1, p. 251 - 260
  作者：Arndt, Silke、Handke, Gabriele、Krause, Norbert

  DOI：——

  日期：——
• Conjugate addition-elimination in the reaction of .beta.-1-alkynyl-9-borabicyclo[3.3.1]nonanes with 4-methoxy-3-buten-2-one and related derivatives. A convenient new route to conjugated enynones
  作者：Gary A. Molander、Herbert C. Brown

  DOI：10.1021/jo00438a038

  日期：1977.9