5-(ethynyl)nona-1,8-dien-5-ol | 177196-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(ethynyl)nona-1,8-dien-5-ol
• 英文别名: 5-ethynyl-nona-1,8-dien-5-ol；5-Ethynylnona-1,8-dien-5-ol
• CAS: 177196-47-3
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: IMVHXGCZTCNUQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 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-(ethynyl)nona-1,8-dien-5-ol 在 N-氯代丁二酰亚胺 、 正丁基锂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 生成 5-(chloroethynyl)-5-<(triethylsilyl)oxy>nona-1,8-diene
  参考文献：
  名称：

  Catalytic Ring Closing Metathesis of Dienynes:  Construction of Fused Bicyclic [n.m.0] Rings

  摘要：

  Ruthenium carbene 1 (Cl-2(PCy(3))(2)Ru=CHCH=CPh(2)) mediates the efficient and selective conversion of acyclic dienynes to fused bicyclic [n.m.O] rings containing five-, six-, and seven-membered rings. Studies with various X-substituted acetylenes (X=H, alkyls, Ph, CO(2)Me, SnBu(3), TMS, Cl, Pr, I) suggest that the dienyne metathesis is sensitive not only to these substituents but also to the catalysts employed. Among the various metal alkylidenes examined, only the ruthenium catalyst 1 exhibited metathesis activity for a range of substrates. These observations further expand the scope of catalytic RCM for the construction of complex organic compounds.

  DOI：

  10.1021/jo951648a
• 作为产物：
  描述：

  4-carboethoxynona-1,8-dien-5-one 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5-(ethynyl)nona-1,8-dien-5-ol
  参考文献：
  名称：

  The quest for planarizing distortions in hydrocarbons: two stereoisomeric [4.5.5.5]fenestranes

  摘要：

  According to semiempirical calculations the planarizing distortions in the central C(C)4 substructure of fenestranes, represented as 1, can be enhanced by a variety of structural modifications. Based on these results we selected the 7-hydroxy-c,c,c,c- and c,t,c,c[4.5.5.5]fenestranones 13 and 16 as precursors for the introduction of a bridgehead double bond. The efficient synthesis of these precursors and their chemical transformations are reported. Attempts to activate the hydroxyl group in 16 for introduction of a bridgehead double bond led to the rearrangement of the [4.5.5.5]fenestrane to a triquinacane skeleton. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.088

文献信息

• The TandemPauson-Khand Reaction
  作者：Marc Thommen、Andrei L. Veretenov、R�gine Guidetti-Grept、Reinhart Keese

  DOI：10.1002/hlca.19960790214

  日期：1996.3.20

  AbstractThe conditions for the novel tandem Pauson‐Khand reaction have been explored. The highly functionalized tetracyclic compounds 11c, 11d, and 16 were prepared from the ene‐diynes 4c, 4d, and 10 by treatment with 2 equiv. of [Co2(CO)8] and 4‐methylmorpholine N‐oxide (NMO) or Me3NO in yields of 24, 22, and 53%, respectively (Table). In the presence of 1–3 equiv. of H2O added to the NMO used for induction of the Pauson‐Khand reaction of 6d, a mixture of cyclopentanones 17/18 and cyclopentenones 12/13 was obtained (Scheme 5). The first example of a [Co2(CO)6]‐induced highly stereoselective ene reaction is described. To account for these results, the formation of intermediates are proposed (Schemes 6 and 7) which hitherto have not been considered in the mechanistic description of the Pauson‐Khand reaction.
• The quest for planarizing distortions in hydrocarbons: two stereoisomeric [4.5.5.5]fenestranes
  作者：Marc Thommen、Lionel Prevot、Marcel K. Eberle、Peter Bigler、Reinhart Keese

  DOI：10.1016/j.tet.2011.03.088

  日期：2011.5

  According to semiempirical calculations the planarizing distortions in the central C(C)4 substructure of fenestranes, represented as 1, can be enhanced by a variety of structural modifications. Based on these results we selected the 7-hydroxy-c,c,c,c- and c,t,c,c[4.5.5.5]fenestranones 13 and 16 as precursors for the introduction of a bridgehead double bond. The efficient synthesis of these precursors and their chemical transformations are reported. Attempts to activate the hydroxyl group in 16 for introduction of a bridgehead double bond led to the rearrangement of the [4.5.5.5]fenestrane to a triquinacane skeleton. (C) 2011 Elsevier Ltd. All rights reserved.
• Catalytic Ring Closing Metathesis of Dienynes:  Construction of Fused Bicyclic [<b><i>n</i></b>.<b><i>m.0] Rings</i></b>
  作者：Soong-Hoon Kim、William J. Zuercher、Ned B. Bowden、Robert H. Grubbs

  DOI：10.1021/jo951648a

  日期：1996.1.1

  Ruthenium carbene 1 (Cl-2(PCy(3))(2)Ru=CHCH=CPh(2)) mediates the efficient and selective conversion of acyclic dienynes to fused bicyclic [n.m.O] rings containing five-, six-, and seven-membered rings. Studies with various X-substituted acetylenes (X=H, alkyls, Ph, CO(2)Me, SnBu(3), TMS, Cl, Pr, I) suggest that the dienyne metathesis is sensitive not only to these substituents but also to the catalysts employed. Among the various metal alkylidenes examined, only the ruthenium catalyst 1 exhibited metathesis activity for a range of substrates. These observations further expand the scope of catalytic RCM for the construction of complex organic compounds.