3,8-nonadiyn-2-ol | 120544-95-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,8-nonadiyn-2-ol
• 英文别名: Nona-3,8-diyn-2-ol
• CAS: 120544-95-8
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: DKSGWXRCSCQVLO-UHFFFAOYSA-N

物化性质

• 沸点：
  222.9±20.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  3,8-nonadiyn-2-ol 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 lithium aluminium tetrahydride 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 (1E)-1-(2-methylenecyclopentylidene)-2-propanol
  参考文献：
  名称：

  Hydroxy group as a regio- and stereochemical control element for sequential metal-catalyzed and thermal cyclizations

  摘要：

  DOI：

  10.1021/jo00271a006
• 作为产物：
  描述：

  1,6-庚二炔 、 乙醛 在 甲基锂 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到3,8-nonadiyn-2-ol
  参考文献：
  名称：

  Pd(0)-催化的 Me3SnSnMe3 与 α,β-炔醛和酮的加成。(Z)-β-三甲基甲锡烷基α,β-烯醛和酮的合成。取代的(Z)-4-三甲基甲锡烷基-1,3-丁二烯的制备和合成用途

  摘要：

  在催化量的 (Ph3P)4Pd 存在下，用 Me3SnSnMe3 处理（干燥四氢呋喃，回流）α,β-炔醛 26-28 和酮 29-36 提供了相当到极好的相应 (Z)-β 产率-三甲基甲锡烷基 α,β-烯醛 41-43 和酮 44-51。羰基化合物 41-51 在适当条件下与亚甲基三苯基正膦反应后，分别顺利转化为 (Z)-4-三甲基甲锡烷基-1,3-丁二烯 61-71。用膦酰基乙酸三甲酯的阴离子处理醛 41 和用膦酰基乙酸酯 73 的阴离子处理醛 42 分别产生极好的 5-三甲基甲锡烷基-2,4-庚二烯酸酯 72 和 74 的产率。(Z)-4-三甲基甲锡烷基-1,3-丁二烯的合成潜力通过将 62 转化为功能化的、

  DOI：

  10.1139/v96-234

文献信息

• Pd(0)-catalyzed addition of Me₃SnSnMe₃ to α,β-alkynic aldehydes and ketones. Synthesis of (<i>Z</i>)-β-trimethylstannyl α,β-alkenic aldehydes and ketones. Preparation and synthetic uses of substituted (<i>Z</i>)-4-trimethylstannyl-1,3-butadienes
  作者：Edward Piers、Richard D. Tillyer

  DOI：10.1139/v96-234

  日期：1996.11.1

  Treatment (dry tetrahydrofuran, reflux) of the α,β-alkynic aldehydes 26–28 and ketones 29–36 with Me3SnSnMe3 in the presence of a catalytic amount of (Ph3P)4Pd provides fair to excellent yields of the corresponding (Z)-β-trimethylstannyl α,β-alkenic aldehydes 41–43 and ketones 44–51. The carbonyl compounds 41–51, upon reaction with methylenetriphenylphosphorane under suitable conditions, are smoothly

  在催化量的 (Ph3P)4Pd 存在下，用 Me3SnSnMe3 处理（干燥四氢呋喃，回流）α,β-炔醛 26-28 和酮 29-36 提供了相当到极好的相应 (Z)-β 产率-三甲基甲锡烷基 α,β-烯醛 41-43 和酮 44-51。羰基化合物 41-51 在适当条件下与亚甲基三苯基正膦反应后，分别顺利转化为 (Z)-4-三甲基甲锡烷基-1,3-丁二烯 61-71。用膦酰基乙酸三甲酯的阴离子处理醛 41 和用膦酰基乙酸酯 73 的阴离子处理醛 42 分别产生极好的 5-三甲基甲锡烷基-2,4-庚二烯酸酯 72 和 74 的产率。(Z)-4-三甲基甲锡烷基-1,3-丁二烯的合成潜力通过将 62 转化为功能化的、
• Hydroxy group as a regio- and stereochemical control element for sequential metal-catalyzed and thermal cyclizations
  作者：Barry M. Trost、Donna C. Lee

  DOI：10.1021/jo00271a006

  日期：1989.5
• TROST, BARRY M.;LEE, DONNA C., J. ORG. CHEM., 54,(1989) N0, C. 2271-2274
  作者：TROST, BARRY M.、LEE, DONNA C.

  DOI：——

  日期：——
• Rh(I)-Catalyzed Pauson−Khand Reaction and Cycloisomerization of Allenynes:  Selective Preparation of Monocyclic, Bicyclo[<i>m</i>.3.0], and Bicyclo[5.2.0] Ring Systems
  作者：Chisato Mukai、Fuyuhiko Inagaki、Tatsunori Yoshida、Katsuya Yoshitani、Yasuyuki Hara、Shinji Kitagaki

  DOI：10.1021/jo050770z

  日期：2005.9.1

  Rhodium(I)-catalyzed PKR of allenynes was found to be applicable for constructing azabicyclo[5.3.0]decadienone as well as oxabicyclo[5.3.0]decadienone frameworks. In addition, a reliable procedure for constructing a 10-monosubstituted bicyclo[5.3.0]deca-1,7-dien-9-one ring system by the rhodium(I)-catalyzed PKR of allenynes was developed under the condition of 10 atm of CO. Investigation of the rhodium(I)-catalyzed

  发现铑（I）催化的烯丙炔的PKR可用于构建氮杂双环[5.3.0]癸二烯酮和氧杂双环[5.3.0]癸二烯酮骨架。此外，在10 atm的条件下，开发了通过铑（I）催化的烯丙炔的PKR构建10-单取代的双环[5.3.0] deca-1,7-dien-9-环系统的可靠方法。氮气氛下铑（I）催化4-苯基磺酰氨基-2,3-dien-8-炔的铑（I）环异构化反应得到相应的环己烯衍生物，而C 1均一化的烯炔根据烯键末端的取代方式，生成环庚烯衍生物和/或双环[5.2.0]壬烯骨架。因此，导致了2- phenylsulfonylbicyclo [5.3.0]癸-1,7-二烯-9-酮（Pauson-Khand反应型产品），3-亚烷基-1的选择性形成起始allenynes和反应条件适当选择-苯基磺酰基-2-乙烯基环庚烯衍生物和双环[5.2.0]壬烯骨架。
• Pd-Catalyzed Cycloisomerization to 1,2-Dialkylidenecycloalkanes. 2. Alternative Catalyst System
  作者：Barry M. Trost、Donna L. Romero、Frode Rise

  DOI：10.1021/ja00089a016

  日期：1994.5

  The mechanisms by which palladium complexes may catalyze the cycloisomerization of 1,6- and 1,7-enynes to dialkylidenecycloalkanes were probed by exploring a catalyst system different than a ligated palladium acetate which previously has proven to be successful. Although carboxylic acids showed no discernible interaction with palladium(0) complexes, this combination proved to be a powerful catalyst system to effect this cycloisomerization. The fact that the two catalyst systems do not have the same reactivity profile suggests this new catalyst system may operate by a different mechanism. Evidence supporting a pathway invoking formation of a hydridopalladium acetate followed by hydropalladation as initiation is presented. Steric and electronic effects direct the regioselectivity of the termination step to form either 1,3- or 1,4-diene products. The 1,3-diene products participate exceedingly well in Diels-Alder reactions, both inter- and intramolecularly. The presence of an oxygen substituent at the position allylic to the diene served as both a regiochemical control element for the palladium-catalyzed cycloisomerization and a diastereochemical control element for the Diels-Alder reaction. The net result of these two steps, the first of which is a catalyzed isomerization and the second an addition, is a highly efficient approach to complex polycycles in terms of both selectivity and atom economy.