(E)-11-hydroxy-1-undecenyl iodide | 87096-20-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-11-hydroxy-1-undecenyl iodide
• 英文别名: (E)-11-iodo-10-undecen-1-ol；(E)-11-iodoundec-10-en-1-ol；(E1)-1-iodoundecen-11-ol
• CAS: 87096-20-6
• 化学式: C₁₁H₂₁IO
• 分子量: 296.192
• InChiKey: WOMWJYHNQSVNDO-CSKARUKUSA-N

物化性质

• 沸点：
  317.2±15.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  13
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-11-hydroxy-1-undecenyl iodide 在 copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 (E)-tetrahydro-2-<(10-hexadecen-12-ynyl)oxy>-2H-pyran
  参考文献：
  名称：

  摘要：

  The sex pheromone of Hemileuca eglanterina from the San Gabriel Mountains, California, was determined to be a combination of E10,Z12-hexadeca-10, 12-dien-1-yl acetate, E10,Z12-hexadeca-10, 12-dien-1-ol, and E10,Z12-hexadeca-10,12-dienal. Ratios of the compounds in extracts of female pheromone glands varied around a mean of 100:48: 1.1 of the acetate, alcohol, and aldehyde, respectively. Field trials with synthetic compounds indicated that the optimum ratio of alcohol to aldehyde was 10:1 and that this ratio was more critical than the ratio of either compound to the acetate. A synthetic blend of 100:10:1 acetate-alcohol-aldehyde was effective at attracting male moths in the field. Additional compounds found in both extract and aeration samples failed to significantly increase trap catches of male moths, although some of these minor components elicited responses from male moth antennae in coupled gas chromatography-electroantennography studies.

  DOI：

  10.1023/a:1020876229787
• 作为产物：
  描述：

  1-壬炔 在 Schwartz's reagent 、 正丁基锂 、 水 、 碘 、 4-甲基苯磺酸吡啶 、 potassium salt of 1,3-diaminopropane 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 26.0h， 生成 (E)-11-hydroxy-1-undecenyl iodide
  参考文献：
  名称：

  Stereospecific palladium-catalyzed coupling reactions of vinyl iodides with acetylenic tin reagents

  摘要：

  DOI：

  10.1021/ja00241a035

文献信息

• New stereospecific syntheses of pheromone bombykol and its three geometrical isomers
  作者：Norio Miyaura、Hiroshi Suginome、Akira Suzuki

  DOI：10.1016/s0040-4039(00)81700-1

  日期：——

  We describe stereospecific syntheses of pheromone, bombykol and the three geometrical isomers by means of the palladium-catalyzed cross-coupling between an appropriate alkenylborane and an alkenyl halide in the presence of a base.

  我们描述了在适当的链烯基硼烷和链烯基卤化物之间在碱的存在下，通过钯催化的交叉偶联，形成的信息素，bombykol和三个几何异构体的立体定向合成。
• Synthesis of both enantiomers of akolactone B and (+)-ancepsenolide
  作者：Gen Hikosaka、Yasunao Hattori、Hidefumi Makabe

  DOI：10.1016/j.tetasy.2014.08.008

  日期：2014.10

  The syntheses of (+)- and (-)-akolactone B and (+)-ancepsenolide were accomplished using a Pd-catalyzed carbonylation. As to the absolute configuration of akolactone B, making a comparison of the specific rotation of both enantiomers of synthetic akolactone B and the natural compound suggests that the absolute configuration at the 4-position of akolactone B is (R). (C) 2014 Elsevier Ltd. All rights reserved.
• Stereo- and regiospecific syntheses to provide conjugated (E,Z)- and (Z,Z)-alkadienes, and arylated (Z)-alkenes in excellent yields via the palladium-catalyzed cross-coupling reactions of (Z)-1-alkenylboronates with 1-bromoalkenes and aryl iodides
  作者：Norio Miyaura、Makoto Satoh、Akira Suzuki

  DOI：10.1016/s0040-4039(00)83869-1

  日期：1986.1
• DOOLITTLE, R. E.;BRABHAM, A.;TUMLINSON, J. H., J. CHEM. ECOL., 16,(1990) N, C. 1131-1153
  作者：DOOLITTLE, R. E.、BRABHAM, A.、TUMLINSON, J. H.

  DOI：——

  日期：——
• MIYAURA NORIO; SATOH MAKOTO; SUZUKI AKIRA, TETRAHEDRON LETT., 27,(1986) N 32, 3745-3748
  作者：MIYAURA NORIO、 SATOH MAKOTO、 SUZUKI AKIRA

  DOI：——

  日期：——