1,3-庚二炔 | 10313-06-1

• 分子结构分类: 有机化合物 - 乙炔化物
• 中文名称: 1,3-庚二炔
• 英文名称: hepta-1,3-diyne
• 英文别名: 1,3-heptadiyne；Hepta-1,3-diin；Heptadiyne
• CAS: 10313-06-1
• 化学式: C₇H₈
• mdl: MFCD00060959
• 分子量: 92.1405
• InChiKey: SVPXILQIPWCHSK-UHFFFAOYSA-N

物化性质

• 沸点：
  50-55 °C(Press: 10 Torr)
• 密度：
  0.828±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2901299090

反应信息

• 作为反应物：
  描述：

  1,3-庚二炔 在 四(三苯基膦)钯 sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 23.0h， 生成 (E)-2-decen-4,6-diynoic acid
  参考文献：
  名称：

  Carpita, Adriano; Neri, Dario; Rossi, Renzo, Gazzetta Chimica Italiana, 1987, vol. 117, # 8, p. 481 - 490

  摘要：

  DOI：
• 作为产物：
  描述：

  2-己炔酸 在 sodium hydroxide 、 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 25.0~750.0 ℃ 、13.33 Pa 条件下， 反应 10.0h， 生成 1,3-庚二炔
  参考文献：
  名称：

  Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 4. Stepwise construction of terminal 1, 3-diynes, conjugated diacetylenic esters and a triacetylenic ester

  摘要：

  Thirteen examples of stabilised alkynoyl ylides 6 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 500 degrees C, to undergo extrusion of Ph(3)PO to give the diacetylenic esters 7 in moderate yield. At 750 degrees C the same ylides afforded terminal 1.3-diynes 8 although often in poor yield. For R = 2-MeSC(6)H(4) both 7 and 8 undergo secondary loss of Me(.) and cyclisation to give 2-alkynylbenzothiophene derivatives 9 and 10 in low yield. The first example of an alkadiynoyl ylide 11 has been prepared and is converted by FVP at 500 degrees C into the triacetylenic ester 12.

  DOI：

  10.1039/p19940002461

文献信息

• Efficient methods for the preparation of acetylenic ketones
  作者：H.D. Verkruijsse、Y.A. Heus-Kloos、L. Brandsma

  DOI：10.1016/0022-328x(88)80002-0

  日期：1988.1

  A number of acetylenic ketones RCCC(O)R′ have been obtained in good yields from lithiated acetylenes RCCLi and acetic anhydride, N,N-dimethylacetamide, or N,N-dimethylbenzamide. The most convenient and general method consists of treating alkynylzinc chlorides with acid halides R′C(O)Cl. Benzoyl chloride (R′ = Ph), acryloyl chloride (R′ = CH2CH), and butynoyl chloride (R′ = C2H5CC) react only

  从锂化乙炔RC CLi和乙酸酐，N，N-二甲基乙酰胺或N，N-二甲基苯甲酰胺以良好的产率获得了许多炔酮RC ＝ CC（＝ O）R′ 。最方便，最通用的方法是用酰基卤R'C（= O）Cl处理炔基氯化锌。苯甲酰氯（R'= Ph），丙烯酰氯（R'= CH 2 = CH ）和丁酰氯（R'= C 2 H 5 C = C ）仅在催化量的Pd [P（P（ Ph）3 ] 4。
• Synthesis, characterization, structure and luminescence studies of mono-, di- and trinuclear gold(I) phosphine alkynyl complexes
  作者：Vivian Wing-Wah Yam、Kai-Leung Cheung、Sung-Kong Yip、Kung-Kai Cheung

  DOI：10.1016/s0022-328x(03)00606-5

  日期：2003.9

  A series of luminescent gold(I) phosphine mono- and diynyl complexes with nuclearity ranging from one to three has been synthesized and characterized; one of them have its crystal structure determined. Their photophysical properties have been studied and emission origin elucidated.

  合成并表征了一系列核原子数为1至3的发光金（I）膦单-和二炔基配合物; 其中之一具有确定的晶体结构。已经研究了它们的光物理性质，并阐明了发射源。
• Total Syntheses of Phomallenic Acids B and C Utilizing Palladium-Catalyzed Coupling of Propargylic Tosylates with Terminal Alkynes
  作者：Masahiro Yoshida、Mohammad Al-Amin、Kozo Shishido

  DOI：10.1055/s-2008-1032116

  日期：——

  Total syntheses of (±)-phomallenic acids B and C, potent FAS II inhibitors, have been achieved by a palladium-catalyzed coupling of propargylic tosylates and terminal alkynes. Attempts to find an enantiospecific coupling using optically active propargylic compounds resulted in racemization of the products.

  (±)-磷烯酸 B 和 C（有效的 FAS II 抑制剂）的全合成已经通过钯催化的炔丙基甲苯磺酸盐和末端炔烃的偶联来实现。使用旋光炔丙基化合物寻找对映体特异性偶联的尝试导致产物的外消旋化。
• 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。
• Enantioselective synthesis of phomallenic acid C, an inhibitor of FAS II pathway
  作者：Ken Ishigami、Tomoko Kato、Kazuaki Akasaka、Hidenori Watanabe

  DOI：10.1016/j.tetlet.2008.06.035

  日期：2008.8

  Enantioselective synthesis of phomallenic acid C, an inhibitor of bacterial FAS II pathway, was successful. Allenyldiyne structure was constructed by a direct anti-SN2′ coupling of propargyl mesylate with diynylindium in the presence of palladium catalyst. Enantiomeric purity was determined by Ohrui–Akasaka method to be 83%ee.

  细菌FAS II途径抑制剂磷丙二酸C的对映选择性合成成功。烯丙基二炔结构是通过在钯催化剂存在下，将炔丙基甲磺酸酯与二炔基吡啶直接抗-S N 2'偶联而构建的。通过Ohrui–Akasaka方法测定对映体纯度为83％ee。