1,3-undecadiyne | 91428-13-6

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 1,3-undecadiyne
• 英文别名: Undecadiyne；undeca-1,3-diyne
• CAS: 91428-13-6
• 化学式: C₁₁H₁₆
• 分子量: 148.248
• InChiKey: RNICAKNKAXVLEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3-undecadiyne 在 四甲基乙二胺 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到8,10,12,14-docosatetrayne
  参考文献：
  名称：

  Balova, I. A.; Remizova, L. A., Russian Journal of Organic Chemistry, 1994, vol. 30, # 2.1, p. 213 - 215

  摘要：

  DOI：
• 作为产物：
  描述：

  1-碘庚烷 在 甲醇 、 methyllithium lithium bromide 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 1,3-undecadiyne
  参考文献：
  名称：

  Synthesis of naturally occurring polyacetylenes via a bis-silylated diyne

  摘要：

  A straightforward synthesis of a series of naturally occurring polyacetylenes has been developed, including the montiporynes A C ells, the atractylodin, with antibiotic at and C, possessing cytotoxic activity against several human solid tumor c activity against Escherichia coli, and triynes, which display insecticidal activities, starting from the readily available 1,4-bis(trimethylsilyl)-1,3-butadiyne. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.043

文献信息

• Synthesis of 1-methyl-4-alkyl-1,3-diacetylenes. Prototropic rearrangement in 1-alkyl-1,3-diacetylenes
  作者：Miguel J Dabdoub、Vânia B Dabdoub、Eder J Lenardão

  DOI：10.1016/s0040-4039(01)00046-6

  日期：2001.3

  lkyl-3,5-diacetylenes with powdered NaOH was used for the synthesis of terminal 1-alkyl-1,3-butadiynes that can be isolated (54–97%) or used in situ. In an attempt to increase the yields of some of the obtained products, different experimental conditions were studied and we found that by using CTAB as a catalyst, a prototropic rearrangement was promoted to afford the 1-methyl-4-alkyl-1,3-diacetylenes

  用NaOH粉末处理2-甲基-2-羟基-6-烷基-3,5-二乙炔用于合成末端1-烷基-1,3-丁二炔，可以分离（54–97％）或使用原地。为了提高某些获得的产品的收率，研究了不同的实验条件，我们发现通过使用CTAB作为催化剂，促质子重排可以提供1-甲基-4-烷基-1,3-乙炔的产率在62-94％之间。
• Zum mechanismus der umlagerung beim alkalischen abbau der quartären salze von 1-dialkylaminoalkadiinen-(2,4)
  作者：K. Schulze、U. Pfüller、M. Mühlstädt

  DOI：10.1016/0040-4020(75)87079-7

  日期：1975.1

  A new rearrangement is observed during the treatment of quaterny salts of diacetylene-Mannichbases with aqueous alkalies; under these conditions 1 - diethylamino - 2,4 - heptadiyne - methojodid smoothly yields 1 - hepten - 3,5 - diyne. The decomposition of 1 - dialkylamino - 2,4 - alkadiynemethojodids with more than 7 C-atoms gives mixtures of 1 - alken - 3,5 - diynes, cis and trans - 5 - alken - 1

  在用碱金属水溶液处理二乙炔-曼尼希碱的季盐过程中观察到新的重排；在这些条件下，1-二乙氨基-2,4-庚二炔-甲jo平稳地产生1-庚烯-3,5-二炔。具有超过7个C原子的1-二烷基氨基-2,4-炔二甲基甲jo的分解产生1-烯烃-3,5-二炔，顺式和反式的混合物-5-烯烃-1,3-二炔顺式和反式-6-阿尔肯-2,4-达因。据推测，该反应是用5-枯烯作为中间体的饮食营养学消除。
• The First Total Synthesis of the Proposed Structure of Montiporyne E
  作者：Christina Collison、Jian Chen、Ryan Walvoord

  DOI：10.1055/s-2006-942441

  日期：——

  isolated from the stony coral Montipora sp., was shown to exhibit cytotoxicity against certain solid tumor cells. Construction of a suitably functionalized α,β-unsaturated lactam for palladium-catalyzed couplings was realized via a Beckmann rearrangement. Subsequent Sonagoshira coupling with a known alkyne chain efficiently afforded the alleged structure of the natural product.

  Montiporyne E 是一种从石珊瑚 Montipora sp. 中分离出来的新型二乙炔内酰胺，已显示出对某些实体瘤细胞的细胞毒性。通过贝克曼重排实现了用于钯催化偶联的适当功能化的 α,β-不饱和内酰胺的构建。随后的 Sonagoshira 与已知的炔烃链偶联有效地提供了所谓的天然产物结构。
• Chiral Propargyl Alcohols via the Enantioselective Addition of Terminal Di- and Triynes to Aldehydes
  作者：Erin R. Graham、Rik R. Tykwinski

  DOI：10.1021/jo2008719

  日期：2011.8.19

  The enantioselective addition of di- and triynes to aldehydes is presented, including the first examples of an asymmetric triyne addition. Modification of the Carreira alkynylation protocol shows that addition of diynes and triynes to alpha-branched aldehydes can be complete in as little as 4 h, and these reactions give good yields and enantioselectivities (up to 98% ee) for di- and triynes tested (aryl, alkyl, and silyl). It is shown for two cases (20 and 24) that products of this asymmetric addition reaction can undergo further manipulation (desilylation and triazole formation) without affecting the enantiopurity.
• Remizova, L. A.; Balova, I. A.; Favorskaya, I. A., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 11, p. 2209 - 2210
  作者：Remizova, L. A.、Balova, I. A.、Favorskaya, I. A.

  DOI：——

  日期：——