2,3-壬二烯 | 22433-34-7

• 分子结构分类: 有机化合物 - 叠烯 - 无环联烯
• 中文名称: 2,3-壬二烯
• 英文名称: nona-2,3-diene
• 英文别名: 2,3-nonadiene；Nona-2,3-dien
• CAS: 22433-34-7
• 化学式: C₉H₁₆
• 分子量: 124.226
• InChiKey: QPYQHAPIBCQICN-UHFFFAOYSA-N

物化性质

• 沸点：
  64-65 °C(Press: 40 Torr)
• 密度：
  0.7555 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2,3-壬二烯 生成 3-壬酮
  参考文献：
  名称：

  Hydroboration of Allenes

  摘要：

  DOI：

  10.1021/ja00893a016
• 作为产物：
  描述：

  1-戊烯-3-炔 在 正丁基锂 、 乙醚 作用下， 生成 2,3-壬二烯
  参考文献：
  名称：

  Petrow; Kormer, Doklady Akademii Nauk SSSR, 1959, vol. 125, p. 1041

  摘要：

  DOI：

文献信息

• An Efficient Photoinduced Iodoperfluoroalkylation of Carbon−Carbon Unsaturated Compounds with Perfluoroalkyl Iodides
  作者：Kaname Tsuchii、Motohiro Imura、Nagisa Kamada、Toshikazu Hirao、Akiya Ogawa

  DOI：10.1021/jo0495889

  日期：2004.10.1

  β-perfluoroalkylated vinylic iodides (R−CHC(I)−CH2−RF) in good yields. The photoinitiated reaction of vinylcyclopropanes (c-C3H5−C(R)CH2) with RF-I proceeds via the rearrangement of cyclopropylcarbinyl radical intermediates to the homoallylic radical intermediates, and the corresponding 1,5-iodoperfluoroalkylated products (I−(CH2)2CHC(R)−CH2−RF) are obtained in high yields. Isocyanides (R−NC), as C−N unsaturated

  取决于所用光源的选择，各种不饱和化合物的光诱导碘全氟烷基化通过自由基机理有效地发生。当通过派热克斯（用氙灯照射ħ ν > 300纳米），末端烯烃（R-CH CH 2）和炔（R-C⋮CH）经历与iodoperfluoroalkylation全氟烷基碘（R ˚F -I）区域选择性地，提供R- CH（I）-CH 2 -R ˚F和-R C（I）-R CH ˚F，分别。在末端异位烯的情况下（R-CH C CH 2），光诱导的碘全氟烷基化选择性地发生在末端双键处，从而以良好的收率得到相应的β-全氟烷基化乙烯基碘（R-CH C（I）-CH 2 -R F）。乙烯基环丙烷（c -C 3 H 5 -C（R）CH 2）与R F -I的光引发反应是通过将环丙基羰基自由基中间体和相应的1,5-碘全氟烷基化产物（I -（CH 2）2 CH C（R）-CH 2 -R F）以高收率获得。异氰酸酯（R-NC），作为C-N不
• Highly regioselective iodoperfluoroalkylation of allenes with perfluoroalkyl iodides upon irradiation with near-UV light
  作者：Akiya Ogawa、Motohiro Imura、Nagisa Kamada、Toshikazu Hirao

  DOI：10.1016/s0040-4039(01)00207-6

  日期：2001.3

  Upon irradiation through Pyrex with a xenon lamp (hν>300 nm), perfluoroalkyl iodides add to terminal allenes regioselectively to afford the corresponding iodoperfluoroalkylated products, where perfluoroalkyl and iodo groups are selectively introduced into the terminal and central carbons of allenes, respectively.

  在用氙灯（hν > 300 nm）通过派热克斯辐照后，全氟烷基碘选择性地加到末端异戊烯中，得到相应的碘全氟烷基化产物，其中全氟烷基和碘基团分别选择性地引入到异戊烯的末端碳和中心碳中。
• Photo-initiated addition of diphenyl diselenide to allenes
  作者：Akiya Ogawa、Kazuyuki Yokoyama、Hiroshi Yokoyama、Masahito Sekiguchi、Nobuaki Kambe、Noboru Sonoda

  DOI：10.1016/s0040-4039(00)97997-8

  日期：1990.1

  Free-radical addition of diphenyl diselenide 2 to allenes 1 took place under irradiation through Pyrex with tungusten lamp to provide 1-(phenylselenomethyl)vinyl selenides 3 in excellent yields.

  自由基加二苯联硒化物的2至丙二烯类1发生照射下通过派热克斯与tungusten灯，以提供1-（phenylselenomethyl）乙烯基硒化物3以优良产率。
• Intermolecular rhodium catalyzed hydroacylation of allenes: the regioselective synthesis of β,γ-unsaturated ketones
  作者：Helen E. Randell-Sly、James D. Osborne、Robert L. Woodward、Gordon S. Currie、Michael C. Willis

  DOI：10.1016/j.tet.2009.03.054

  日期：2009.6

  A variety of β-S-substituted aldehydes undergo efficient and regioselective rhodium catalyzed hydroacylation reactions with 1,3-disubstituted and 1,1,3-trisubstituted allenes, to deliver β,γ-unsaturated ketone products. Regioselectivites are controlled primarily by steric factors. The reactions are catalyzed by the complex [Rh(dppe)]ClO4.

  多种β- S-取代的醛与1,3-二取代和1,1,3-三取代的烯类进行有效的区域选择性铑催化的加氢酰化反应，以生成β，γ-不饱和酮产物。区域选择性主要受空间因素控制。该反应由络合物[Rh（dppe）] ClO 4催化。
• Palladium-catalyzed hydroselenation of allenes with benzeneselenol
  作者：Akiya Ogawa、Atsulo Kudo、Toshikazu Hirao

  DOI：10.1016/s0040-4039(98)01024-7

  日期：1998.7

  Palladium(II) acetate (Pd(OAc)(2)) catalyzes the addition of benzeneselenol to allenes, providing the corresponding vinylic selenides in good yields. In contrast to the oxygen-induced radical addition of PhSe11 to terminal allenes, which occurred at the terminal double bond preferentially, the present palladium-catalyzed hydroselenation to terminal allenes affords the internal adduct preferentially; thus, these two reactions are complementary to each other for the synthesis of vinylic selenides. (C) 1998 Elsevier Science Ltd. All rights reserved.