2,19-heneicosadiyn-11-one | 1488-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,19-heneicosadiyn-11-one
• 英文别名: heneicosa-2,19-diyn-11-one；Henicosa-2,19-diyn-11-one
• CAS: 1488-78-4
• 化学式: C₂₁H₃₄O
• 分子量: 302.5
• InChiKey: SDGRPRKFYHHDOW-UHFFFAOYSA-N

物化性质

• 熔点：
  61 °C(Solv: ethanol (64-17-5))
• 沸点：
  428.8±30.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  2,19-heneicosadiyn-11-one 在 Lindlar's catalyst 喹啉 、 Tris(t-butoxy)(2,2-dimethylpropylidyne)tungsten(VI), 98% Schrock Alkyne Metathesis Catalyst 、 氢气 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 2.5h， 生成 灵猫酮
  参考文献：
  名称：

  Ring closing alkyne metathesis: stereoselective synthesis of civetone

  摘要：

  A concise and stereoselective synthesis of the macrocyclic musk civetone 6 is reported starting from readily available 9-undecynol. The key steps comprise a ring closing metathesis of diyne 4 followed by Lindlar reduction of the resulting cycloalkyne 5. The cyclization can be effected either by using catalytic amounts of the Schrock alkylidyne complex (t-BuO)(3)W drop CCMe3 or by means of an in situ catalyst mixture generated from Mo(CO)(6) and p-trifluoromethylphenol. Both catalyst systems turned out to be compatible with the unprotected ketone function of the substrate. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00096-6
• 作为产物：
  描述：

  9-undecynoic acid chloride 生成 2,19-heneicosadiyn-11-one
  参考文献：
  名称：

  Notes

  摘要：

  DOI：

  10.1039/jr9650003473

文献信息

• Alkyne Metathesis: Development of a Novel Molybdenum-Based Catalyst System and Its Application to the Total Synthesis of Epothilone A and C
  作者：Alois Fürstner、Christian Mathes、Christian W. Lehmann

  DOI：10.1002/1521-3765(20011217)7:24<5299::aid-chem5299>3.0.co;2-x

  日期：2001.12.17

  as 15, 16 and 20 which themselves were shown to be catalytically active. Numerous applications illustrate the performance of the catalytic system 1/CH2Cl2 which operates under mild conditions and tolerates an array of polar functional groups. The wide scope allows the method to be implemented into the total synthesis of sensitive and polyfunctional natural products. Most notable among them is a concise

  通式为[Mo [（tBu）（Ar）N] 3]的受阻位钼（III）酰胺配合物，在用CH2Cl2或其他卤素供体处理后，已转变成用于各种炔烃的高效催化剂复分解反应。尽管原位形成的繁殖物种的实际性质仍然难以捉摸，但卤素转移到1的Mo中心在此类预催化剂的活化中起着决定性的作用。通过X射线晶体学可以分离和表征一些所得的卤化钼衍生物，例如15、16和20，它们本身显示出催化活性。许多应用程序说明了催化系统1 / CH2Cl2的性能，该系统在温和条件下运行并能耐受一系列极性官能团。广泛的范围使该方法可用于敏感和多官能天然产物的全合成。其中最引人注目的是简要介绍有效的抗癌药埃坡霉素A（86）和C（88）。这些目标的大环内酯核心是通过二炔113的闭环炔烃复分解（RCAM）进行锻造，然后对由此形成的环炔114进行Lindlar加氢。由于该策略打开了对（Z）-烯烃115的立体选择入口，因此该方法固有地比基于常规R
• (E)-Cycloalkenes and (E,E)-cycloalkadienes by ring closing diyne- or enyne–yne metathesis/semi-reduction
  作者：Fabrice Lacombe、Karin Radkowski、Günter Seidel、Alois Fürstner

  DOI：10.1016/j.tet.2004.05.042

  日期：2004.8

  A concise, practical and stereoselective entry into macrocyclic (E)-alkenes is outlined comprising a sequence of ring closing alkyne metathesis (RCAM), trans-selective hydrosilylation of the resulting cycloalkynes catalyzed by [Cp*Ru(MeCN)(3)]PF6, and a protodesilylation of the ensuing vinylsilanes with AgF in aq. THF/MeOH. Moreover, the first examples of intramolecular enyne-yne metathesis reactions catalyzed by the Schrock alkylidyne complex (tBUO)(3)W drop CCMe3 are reported; the resulting cyclic enynes can be converted along similar lines into the corresponding (E,E)-configured 1,3-dienes in good overall yields. Cycloalkyne 4 and the (E)-configured cyclic olefins 6 and 21 were characterized by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.
• Notes
  作者：C.-Y. Chen、R. J. W. Le Fèvre、K. K. Chakravarti、U. G. Nayak、S. C. Bhattacharyya、V. K. Balakrishnan、R. K. Razdan、A. S. Kertes、P. J. Lloyd、J. A. Reader、P. W. G. Smith、N. Boden、J. Feeney、L. H. Sutcliffe、R. J. Ferrier、W. G. Overend、A. E. Ryan、Johannes Dale、Raymond Coulon、H. El Khadem、M. M. Abdel Rahman、G. Birch、C. W. Bird、J. H. Knox、J. M. C. Turner、M. C. Ganorkar、M. H. B. Stiddard、D. A. H. Taylor、S. Nadkarni、N. R. Williams、A. H. Jackson、A. E. Smith、J. McKechnie、D. S. Payne、W. Sim、W. J. Feast、R. Stephens

  DOI：10.1039/jr9650003473

  日期：——
• Ring closing alkyne metathesis: stereoselective synthesis of civetone
  作者：Alois Fürstner、Günter Seidel

  DOI：10.1016/s0022-328x(00)00096-6

  日期：2000.7

  A concise and stereoselective synthesis of the macrocyclic musk civetone 6 is reported starting from readily available 9-undecynol. The key steps comprise a ring closing metathesis of diyne 4 followed by Lindlar reduction of the resulting cycloalkyne 5. The cyclization can be effected either by using catalytic amounts of the Schrock alkylidyne complex (t-BuO)(3)W drop CCMe3 or by means of an in situ catalyst mixture generated from Mo(CO)(6) and p-trifluoromethylphenol. Both catalyst systems turned out to be compatible with the unprotected ketone function of the substrate. (C) 2000 Elsevier Science S.A. All rights reserved.