undec-3-yn-2-one | 62967-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: undec-3-yn-2-one
• CAS: 62967-60-6
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: QPYADGGBCPWJTK-UHFFFAOYSA-N

物化性质

• 沸点：
  238.9±23.0 °C(Predicted)
• 密度：
  0.872±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  undec-3-yn-2-one 在 lithium aluminium tetrahydride 、 (R)-Chirald 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (S)-1-methyl-2-decynyl methanesulfonate
  参考文献：
  名称：

  Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes

  摘要：

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

  DOI：

  10.1021/jo00030a036
• 作为产物：
  描述：

  1-壬炔 在 正丁基锂 、 pyridinium chloroformate 作用下， 以 二氯甲烷 为溶剂， 生成 undec-3-yn-2-one
  参考文献：
  名称：

  [2,3] Wittig rearrangement of nonracemic propargyl ethers leading to allenes of high stereochemical integrity

  摘要：

  DOI：

  10.1021/jo00286a013

文献信息

• Structure Investigations of (ent)-Cladospolide D by De Novo Synthesis and Kinetic and Thermodynamic Isomerization
  作者：John Penn、George O’Doherty、Yalan Xing

  DOI：10.1055/s-0029-1217606

  日期：2009.9

  dihydroxylation of a dienoate installed the remaining stereochemistry. The de novo asymmetric route allowed for the asymmetric synthesis of three members of the cladospolide natural products and correctly established the structure for cladospolide D. cladospolides B-D - asymmetric synthesis - natural product synthesis - E/Z-alkene isomerization

  从非手性非1-炔实现了cladospolides B和C和（ent）-cladospolide D的从头不对称合成。11-13步的路线依赖于Noyori还原反应和KAPA促进的炔烃拉链反应，以跨越九个碳原子片段传递非手性官能团并实现二烯酸官能团的安装。二烯酸酯的非对映选择性和区域选择性Sharpless二羟基化反应可保留剩余的立体化学。从头不对称路线允许克拉多波德天然产物的三个成员的不对称合成，并正确建立了克拉多波德D的结构。 cladospolides BD-不对称合成-天然产物合成-E / Z-烯烃异构化
• De Novo Asymmetric Synthesis of Cladospolide B−D: Structural Reassignment of Cladospolide D via the Synthesis of its Enantiomer
  作者：Yalan Xing、George A. O’Doherty

  DOI：10.1021/ol9000119

  日期：2009.3.5

  The enantioselective synthesis of cladospolide B, C, and (ent)-cladospolide D has been achieved in 11−15 steps from 1-nonyne. The route relies upon an alkyne zipper reaction to relay an ynone and dienoate functional groups across a nine carbon fragment, which enables a highly enantioselective Noyori ynone reduction and a diastereo- and regioselective Sharpless dihydroxylation of a dienoate. In addition

  从1壬炔起11-15步就完成了对克拉多普列B，C和（ent）-克拉多普列D的对映选择性合成。该路线依赖于炔烃拉链反应，将九个碳片段上的炔酮和二烯酸酯官能团进行中继，从而实现高度对映选择性的Noyori炔酮还原，以及二烯酸酯的非对映选择性和区域选择性Sharpless二羟基化反应。除了对克拉多波利斯自然产品的三个成员采取灵活的方法外，这条路线首次正确地建立了克拉多波利斯D的结构。
• Stereospecific synthesis of trisubstituted and tetrasubstituted olefins. Conjugate addition of dialkylcopper-lithium reagents to .alpha.,.beta.-acetylenic esters
  作者：Elias J. Corey、John A. Katzenellenbogen

  DOI：10.1021/ja01035a045

  日期：1969.3
• Highly stereoselective isomerization of ynones to conjugated dienones catalyzed by transition-metal complexes
  作者：Dawei Ma、Yihua Yu、Xiyan Lu

  DOI：10.1021/jo00266a021

  日期：1989.3
• Cu(I)-Catalyzed Macrocyclic Sonogashira-Type Cross-Coupling
  作者：Jeffrey Santandrea、Anne-Catherine Bédard、Shawn K. Collins

  DOI：10.1021/ol501898b

  日期：2014.8.1

  A macrocyclic Cu-catalyzed Sonogashira-type cross-coupling reaction has been developed that employs an operationally simple CuCl/phen/Cs2CO3 catalyst system. Macrocyclizations can be performed at relatively high concentrations without the need for slow addition techniques and form macrocycles with various ring sizes and functional groups. The optimized protocol was employed in the synthesis of (S)-zearalane, demonstrating applicability toward the synthesis of a macrocycle with known biological activity.