1,1-diethoxy-3-nonyne | 90290-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-diethoxy-3-nonyne
• 英文别名: 3-nonynal diethyl acetal；1,1-Diethoxynon-3-yne
• CAS: 90290-02-1
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: OYMOWDHUHOFIJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  274.3±30.0 °C(Predicted)
• 密度：
  0.886±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1-diethoxy-3-nonyne 在 二氯二茂钛 、 四(三苯基膦)钯 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium hydroxide 、 sodium hydroxide 、 正丁基锂 、 三丁基锡锂 、 L-(+)-酒石酸二异丙酯 、 4 A molecular sieve 、 2,5-二叔丁基对苯二酚 、 ISOBUTYLMAGNESIUM BROMIDE 、 四丁基氟化铵 、 碘 、 二(3-甲基丁烷-2-基)硼烷 、 草酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 61.0h， 生成 白三烯B4
  参考文献：
  名称：

  Highly stereocontrolled total synthesis of leukotriene B4, 20-hydroxyleukotriene B4, leukotriene B3, and their analogs

  摘要：

  DOI：

  10.1021/jo00306a007
• 作为产物：
  描述：

  3-壬炔-1-醇 在 camphor-10-sulfonic acid 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,1-diethoxy-3-nonyne
  参考文献：
  名称：

  Wavarin, Laurence; Viala, Jacques, Synthesis, 2002, # 3, p. 326 - 330

  摘要：

  DOI：

文献信息

• A NEW APPROACH TO (±)-LEUKOTRIENE A₄METHYL ESTER
  作者：Sadao Tsuboi、Toshihide Masuda、Akira Takeda

  DOI：10.1246/cl.1983.1829

  日期：1983.12.5

  A stereoselective synthesis of (2E,4Z,7Z)-2,4,7-tridecatrienol, a key intermediate in the synthesis of leukotriene A4 methyl ester, is established via alumina-promoted rearrangement of ethyl (7Z)-3,4,7-tridecatrienoate to ethyl (2E,4Z,7Z)-2,4,7-tridecatrienoate as a key step.

  (2E,4Z,7Z)-2,4,7-十三碳三烯醇是合成白三烯 A4 甲酯的关键中间体，通过氧化铝促进乙基 (7Z)-3,4,7 重排建立立体选择性合成-十三碳三烯酸乙酯到 (2E,4Z,7Z)-2,4,7-十三碳三烯酸乙酯作为关键步骤。
• Nonshita, Katsumasa; Banno, Hiroshi; Maruoka, Keiji, Journal of the American Chemical Society, 1990, vol. 112, # 1, p. 316 - 322
  作者：Nonshita, Katsumasa、Banno, Hiroshi、Maruoka, Keiji、Yamamoto, Hishashi

  DOI：——

  日期：——
• Chemo-enzymatic enantio-convergent asymmetric total synthesis of (S)-(+)-dictyoprolene using a kinetic resolution—stereoinversion protocol
  作者：Andreas Wallner、Harald Mang、Silvia M. Glueck、Andreas Steinreiber、Sandra F. Mayer、Kurt Faber

  DOI：10.1016/s0957-4166(03)00481-6

  日期：2003.8

  A single enantiomer of a (stereo)chemically labile allylic-homoallylic alcohol was obtained in 91% e.e. and 96% yield from the racemate by employing a lipase-catalysed kinetic resolution coupled to in situ inversion under carefully controlled (Mitsunobu) conditions in order to Suppress side reactions, such as elimination and racemisation. This technique was Successfully applied to an enantio-convergent asymmetric total synthesis of the algal fragrance component (S)-dictyoprolene. (C) 2003 Elsevier Ltd. All rights reserved.
• Independent Synthesis, Solution Behavior, and Studies on the Mechanism of Formation of a Primary Amine-Derived Fluorophore Representing Cross-linking of Proteins by (<i>E</i>)-4-Hydroxy-2-nonenal
  作者：Guozhang Xu、Yahua Liu、Lawrence M. Sayre

  DOI：10.1021/jo982523j

  日期：1999.8.1

  Lipid peroxidation in aging and degenerative disease results in the production of 4-hydroxy-2-alkenals that modify proteins and give rise to both protein cross-linking and fluorophore generation. Recent model studies demonstrated that the major ex/em 360/430 fluorophore formed from (E)-4-hydroxy-2-nonenal (HNE) or (E)-4-hydroxy-2-hexenal (HHE) and protein lysine-based amine is a 2-alkyl-2-hydroxy-1,2-dihydropyrrol-3-one iminium 1:2 cross-link (1), a structure that is further confirmed here using N-15-labeling, and which has pH stability characteristics the same as those of lipofuscin pigments isolated from human tissues. Fluorophore generation represents an overall four-electron oxidation, requires dioxygen, and is enhanced by the presence of Cu(II). The HNE-propylamine-derived fluorophore 1a was independently synthesized from either 3,4-dioxononanal (8) or (E)-4-oxo-2-nonenal (13), providing further evidence for its assigned structure and clues to how it forms from HNE. Mechanistic studies on HNE-derived fluorophore formation permit ruling out the initial reversible HNE-derived Schiff base Michael adduct (17) as an intermediate. In addition, the structurally related non-cross-link 2-pentyl-2-hydroxy-1,2-dihydropyrrol-3-one 9a that forms along with 1a from 8 does not form from HNE and does: not serve as a precursor to la in the HNE-amine reaction system. A mechanism involving two 2e oxidations following initial Schiff base formation is proposed that is consistent with intermediates independently accessed from 8 and 13.
• NONOSHITA, KATSUMASA;BANNO, HIROSHI;MARUOKA, KEIJI;YAMAMOTO, HISASHI, J. AMER. CHEM. SOC., 112,(1990) N, C. 316-322
  作者：NONOSHITA, KATSUMASA、BANNO, HIROSHI、MARUOKA, KEIJI、YAMAMOTO, HISASHI

  DOI：——

  日期：——