7-甲基-9-十五烷酮 | 177665-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 7-甲基-9-十五烷酮
• 英文名称: 9-methylpentadecan-7-one
• 英文别名: 9-Methyl-7-pentadecanone
• CAS: 177665-51-9
• 化学式: C₁₆H₃₂O
• 分子量: 240.429
• InChiKey: YUFIIMXGQPZRNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-甲基-9-十五烷酮 、 甲胺 在 镍 作用下， 生成 (1-hexyl-3-methyl-nonyl)-methyl-amine
  参考文献：
  名称：

  US2160058

  摘要：

  公开号：
• 作为产物：
  描述：

  dicapryl alcohol 在 铬酸 作用下， 生成 7-甲基-9-十五烷酮
  参考文献：
  名称：

  Guerbet, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1910, vol. 150, p. 980

  摘要：

  DOI：

文献信息

• Self-coupling of secondary alcohols by Ni/CeO2 catalyst
  作者：Katsuya Shimura、Kenichi Kon、S.M.A. Hakim Siddiki、Ken-ichi Shimizu

  DOI：10.1016/j.apcata.2013.04.040

  日期：2013.7

  heterogeneous catalytic system for the self-coupling of secondary alcohols under mild conditions. Effects of support material and oxidation state of Ni on the activity are studied and it is found that both CeO2 and metallic Ni are indispensable for the reaction. A possible reaction mechanism is proposed, in which ketones, formed by dehydrogenation of alcohol, undergone Aldol condensation to give α,β-unsaturated

  研究了负载型镍催化剂在N 2气氛下无添加剂条件下脂族仲醇的液相C C自偶联。在各种Ni催化剂中，在H 2中预先还原的1或3 wt％Ni / CeO 2催化剂显示1-辛醇在130°C时自偶合的二聚产物（较高的酮）收率最高（94％）。 ，并且催化剂被重复使用。该催化剂对于各种仲醇的自偶联也是有效的，为温和条件下仲醇的自偶联提供了第一个非均相催化体系。研究了载体材料和Ni的氧化态对活性的影响，发现CeO 2金属镍对于该反应是必不可少的。提出了一种可能的反应机理，其中将由醇脱氢形成的酮进行醛醇缩合反应，生成α，β-不饱和酮，最后将其通过原位形成的Ni H物种进行氢化。
• Tripodal N,P Mixed-Donor Ligands and Their Cobalt Complexes: Efficient Catalysts for Acceptorless Dehydrogenation of Secondary Alcohols
  作者：Shi Xu、Latifah M. Alhthlol、Keshav Paudel、Eric Reinheimer、David L. Tyer、Daniela K. Taylor、Amberlynn M. Smith、Jonathan Holzmann、Edgar Lozano、Keying Ding

  DOI：10.1021/acs.inorgchem.8b00043

  日期：2018.3.5

  A new tetradentate tripodal ligand, iPrPPPNHPyMe, and the cobalt complexes were synthesized and characterized. The well-defined cobalt complexes efficiently catalyzed acceptorless dehydrogenation of secondary alcohols into ketones.

  合成并表征了新的四齿三脚架配体iPr PPPN H Py Me和钴配合物。定义明确的钴络合物可有效地催化仲醇的无受体脱氢反应成酮。
• Chiral Synthesis via Organoboranes. 47. Efficient Synthesis of Unsymmetrical Ketones and Enantiomerically Pure Spiroketals Using (±)-Isopinocampheyldichloroborane
  作者：Herbert C. Brown、Shekhar V. Kulkarni、Uday S. Racherla、Ulhas P. Dhokte

  DOI：10.1021/jo980989w

  日期：1998.10.1

  intermediate was readily converted into the unsymmetrical ketones, R(1)COR(2), in high yields and purity, by an established method. This methodology was successfully applied to the synthesis of enantiomerically pure spiroketals using optically pure TBS ether protected homoallylic alcohols as the alkenes for stepwise hydroboration.

  现成的且稳定的（+/-）-异樟脑基二氯硼烷[（+/-）-IpcBCl（2）]使用原位还原-氢硼化方案方便地用于两个不同烯烃的逐步氢硼化，从而得到混合的三烷基硼烷IpcBR（1 R（2）。通过用醛RCHO处理从这些三烷基硼烷中方便地消除α-pine烯，提供了硼酸酯R（1）R（2）BOCH（2）R。通过建立的方法，该中间体很容易以高收率和高纯度转化为不对称酮R（1）COR（2）。该方法已成功地应用于光学纯的TBS醚保护的均烯丙基醇作为烯烃进行逐步硼氢化的对映体纯螺环酮的合成。
• Use of (±)-isopinocampheyldichloroborane for the efficient synthesis of unsymmetrical ketones via stepwise hydroboration of alkenes
  作者：Shekhar V. Kulkarni、Ulhas P. Dhokte、Herbert C. Brown

  DOI：10.1016/0040-4039(96)00161-x

  日期：1996.3

  A convenient, one-pot synthesis of unsymmetrical ketones has been developed making use of the in situ reduction — hydroboration reactions of readily prepared and stable (±)-isopinocampheyldichloroborane.

  已经开发出一种方便的一锅合成不对称酮的方法，该方法利用原位还原-易于制备且稳定的（±）-异樟脑基二氯硼烷进行硼氢化反应。
• Ruthenium-Catalyzed Self-Coupling of Primary and Secondary Alcohols with the Liberation of Dihydrogen
  作者：Ilya S. Makarov、Robert Madsen

  DOI：10.1021/jo4008699

  日期：2013.7.5

  The dehydrogenative self-condensation of primary and secondary alcohols has been studied in the presence of RuCl2(IiPr)(p-cymene). The conversion of primary alcohols into esters has been further optimized by using magnesium nitride as an additive, which allows the reaction to take place at a temperature and catalyst loading lower than those described previously. Secondary alcohols were dimerized into racemic ketones by a dehydrogenative Guerbet reaction with potassium hydroxide as the additive. The transformation gave good yields of the ketone diners with a range of alkan-2-ols, whereas more substituted secondary alcohols were unreactive. The reaction proceeds by dehydrogenation to the ketone, followed by an aldol reaction and hydrogenation of the resulting enone.