1,1-diethoxy-2,4-pentadiyne | 3777-61-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-diethoxy-2,4-pentadiyne
• 英文别名: 5,5-diethoxy-penta-1,3-diyne；5,5-diethoxypenta-1,3-diyne
• CAS: 3777-61-5
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: IXRADJWNHDPLGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,1-diethoxy-2,4-pentadiyne 在 甲酸 、 盐酸羟胺 、 乙胺 、 copper(l) chloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 9-hydroxynona-2,4,6-triynal
  参考文献：
  名称：

  Macrides, Theodore A.; Thaller, Viktor, Journal of Chemical Research, Miniprint, 1981, # 6, p. 2001 - 2016

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-1-chloro-5,5-diethoxy-1-penten-3-yne 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以33%的产率得到1,1-diethoxy-2,4-pentadiyne
  参考文献：
  名称：

  Reactive Carbon-Chain Molecules:  Synthesis of 1-Diazo-2,4-pentadiyne and Spectroscopic Characterization of Triplet Pentadiynylidene (H−C⋮C−C̈−C⋮C−H)

  摘要：

  1-Diazo-2,4-pentadiyne (6a), along with both monodeuterio isotopomers; 6b and 6c, has been synthesized via a route that proceeds through diacetylene, 2,4-pentadiynal, and 2,4-pentadiynal tosylhydrazone. Photolysis of diazo compounds 6a-c (lambda > 444 nm; Ar or N-2, 10 K) generates triplet carbenes HC5H (1) and HC5D (1-d), which have been characterized by IR, EPR, and UV/vis spectroscopy. Although many resonance structures contribute to the resonance hybrid for this highly unsaturated carbon-chain molecule, experiment and theory reveal that the structure is best depicted in terms of the dominant resonance contributor of penta-1,4-diyn-3-ylidene (diethynylcarbene, H-C equivalent to C-C-C equivalent to C-H). Theory predicts an axially symmetric (D-h) structure and a triplet electronic ground state for 1 (CCSD(T)/ANO). Experimental IR frequencies and isotope shifts are in good agreement with computed values. The triplet EPR spectrum of 1 (vertical bar D/hc vertical bar = 0.6157 cm(-1), vertical bar E/hc vertical bar = 0.0006 cm(-1)) is consistent with an axially symmetric structure, and the Curie law behavior confirms that the triplet state is the ground state. The electronic absorption spectrum of 1 exhibits a weak transition near 400 nm with extensive vibronic coupling. Chemical trapping of triplet HC5H (1) in an O-2-cloped matrix affords the carbonyl oxide 16 derived exclusively from attack at the central carbon.

  DOI：

  10.1021/ja058252t

文献信息

• Natural acetylenes. Part XL. Syntheses of polyacetylenic C18 and C16 esters with 9-ene-12,14-diyne unsaturation, and their labelling
  作者：Alexander G. Fallis、Milton T. W. Hearn、Ewart R. H. Jones、Viktor Thaller、John L. Turner

  DOI：10.1039/p19730000743

  日期：——

  The esters R[CC]2·CH2CH[graphics omitted]CH·[CH2]7·CO2MeR = Me[CH2]2, MeCC, cis- or trans-MeCHCH, trans-HO·CH2·CHCH, HO·CH2·CC, cis- or trans-MeO2C·CHCH, MeO2C·CC, (EtO)2CH, OHC, or, H2N·OC} were prepared from the Wittig salt Me3Si·CC·CH2·CH2·PPh3I–via ICC·CH2·CH[graphics omitted]CH·[CH2]7·CO2Me; several were specifically labelled [at C(9), C(17), and C(18)]. The Wittig salt offers a general route

  酯R [C C] 2 ·CH 2 CH [省略图形] CH·[CH 2 ] 7 ·CO 2 Me R = Me [CH 2 ] 2，MeC C，顺式或反式-MeCH CH，反式- HO·CH 2 ·CH CH，HO·CH 2 ·C C，顺式-或反式-MeO 2 C·CH CH，的MeO 2 C·ç C，（ETO）2 CH，OHC，或者，H 2 N·OC }由维蒂希盐Me 3 Si·C C·CH制备2 ·CH 2 ·PPh 3 I –通过ICC·CH 2 ·CH [省略图形] CH·[CH 2 ] 7 ·CO 2 Me；其中几个被专门标记[在C（9），C（17）和C（18）]。维蒂希盐为通向1-烯-4,6-二炔和更高度不饱和的跳过的烯炔体系提供了一条一般路线。
• Gorgues,A.; Levas,E., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1969, vol. 268, p. 1905 - 1908
  作者：Gorgues,A.、Levas,E.

  DOI：——

  日期：——
• A mild synthesis of 1,3-diynes
  作者：Andrew S. Kende、Cynthia A. Smith

  DOI：10.1021/jo00246a057

  日期：1988.5
• KENDE, ANDREW S.;SMITH, CYNTHIA A., J. ORG. CHEM., 53,(1988) N 11, 2655-2657
  作者：KENDE, ANDREW S.、SMITH, CYNTHIA A.

  DOI：——

  日期：——