5-hydroxy-4,6-dimethyl-3-heptanone | 71699-33-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-hydroxy-4,6-dimethyl-3-heptanone
• 英文别名: 5-hydroxy-4,6-dimethylheptan-3-one；(4RS,5SR)-5-hydroxy-4,6-dimethyl-3-heptanone；(4RS,5SR)-5-hydroxy-4,6-dimethyl-heptan-3-one；(4S,5R)-5-hydroxy-4,6-dimethylheptan-3-one
• CAS: 71699-33-7
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: BIEQEQORPVLGMS-VXNVDRBHSA-N

物化性质

• 沸点：
  232.5±13.0 °C(Predicted)
• 密度：
  0.915±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4,6-dimethyl-3-heptanone 在 tetramethylammonium triacetoxyborohydride 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 以76%的产率得到2,4-dimethylheptane-3,5-diol
  参考文献：
  名称：

  Evans−Tishchenko Coupling of Heteroaryl Aldehydes

  摘要：

  The low-temperature Evans-Tishchenko coupling of a range of functionalized heteroaryl aldehydes with beta-hydroxy ketones in the presence of a Sm(III) catalyst has been achieved with high yields (90-99%) and good to excellent diastereoselectivity (90:10 -> 95:5 dr). However, at room temperature a retro-aldol aldol-Tishchenko reaction was found to compete with the desired Evans-Tishchenko reaction. Identification of these byproducts has allowed the corresponding aldol-Tishchenko reaction to be optimized for several heteroaryl aldehydes.

  DOI：

  10.1021/jo1015689
• 作为产物：
  描述：

  2-iodopentan-3-one 在 2,6-二甲基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 5-hydroxy-4,6-dimethyl-3-heptanone
  参考文献：
  名称：

  通过由 α-碘酮和 9-BBN-H 生成的硼烯醇化物进行立体选择性交叉羟醛反应

  摘要：

  通过用 9-BBN-H 处理 α-碘酮，原位顺利生成硼烯醇化物，并通过与各种醛在低温下连续反应以高度非对映选择性的方式生成醛醇。

  DOI：

  10.1246/cl.2002.698

文献信息

• Synthetic control leading to chiral compounds
  作者：Teruaki Mukaiyama、Nobuharu Iwasawa、Rodney W. Stevens、Toru Haga

  DOI：10.1016/s0040-4020(01)82423-6

  日期：1984.1

  A highly diastereoselective cross aldol reaction is developed using divalent tin enolates formed from stannous trifluoromethanesulfonate and carbonyl compounds. The reaction is extended to a highly enantioselective cross aldol reaction employing chiral diamines derived from (S)-proline as ligands.

  使用由三氟甲烷磺酸亚锡和羰基化合物形成的二价烯醇锡开发了高度非对映选择性的交叉醇醛缩合反应。使用衍生自（S）-脯氨酸的手性二胺作为配体，将反应扩展至高度对映选择性的交叉羟醛反应。
• Diastereoselective Aldol and Reformatsky Reactions of<b><i>α</i></b>-Halo Carbonyl Compounds and Aldehydes Mediated by Titanium(II) Chloride
  作者：Akifumi Kagayama、Koji Igarashi、Isamu Shiina、Teruaki Mukaiyama

  DOI：10.1246/bcsj.73.2579

  日期：2000.11

  Highly diastereoselective aldol reactions of α-bromo ketones with several aldehydes were successfully carried out by using a combination of titanium(II) chloride and copper or sodium iodide in dichloromethane-pivalonitrile at low temperature. Similarly, Reformatsky reactions of α-bromo thioester with aliphatic aldehydes proceeded to afford β-hydroxy thioesters in good yields under mild conditions.

  通过在低温下在二氯甲烷-新戊腈中使用氯化钛 (II) 和碘化铜或碘化钠的组合，成功地进行了 α-溴酮与几种醛的高度非对映选择性羟醛反应。类似地，α-溴硫酯与脂肪醛的 Reformatsky 反应在温和条件下以良好的产率得到 β-羟基硫酯。
• Direct, practical, and powerful crossed aldol additions between ketones and ketones or aldehydes utilizing environmentally benign TiCl4–Bu3N reagent
  作者：Yoo Tanabe、Noriaki Matsumoto、Takahiro Higashi、Tomonori Misaki、Tomotaka Itoh、Misako Yamamoto、Kumi Mitarai、Yoshinori Nishii

  DOI：10.1016/s0040-4020(02)00977-8

  日期：2002.10

  benign method is advantageous from a green chemical viewpoint with regard to yield, substrates variation, reagent availability, and simple procedures. This method was applied to a short step formal synthesis of (R)-muscone, a natural macrocyclic musk.

  在酮和酮或醛之间进行了有效的TiCl 4 -Bu 3 N-（cat。TMSCl）促进的羟醛添加。从绿色化学观点来看，该环境友好方法在产率，底物变化，试剂可用性和简单程序方面是有利的。该方法用于天然大环麝香（R）-muscone的短步正式合成。
• TiCl4/Bu3N/(catalytic TMSOTf): Efficient agent for direct aldol addition and Claisen condensation
  作者：Yoshihiro Yoshida、Ryosuke Hayashi、Hiromasa Sumihara、Yoo Tanabe

  DOI：10.1016/s0040-4039(97)10320-3

  日期：1997.12

  efficient cross aldol additions between different ketones and between ketones and aldehydes, in good to excellent yields with high syn-stereoselectivities. As an extension, direct Claisen condensation between methyl esters was also promoted by TiCl4/Bu3N with 0.05 equiv of TMSOTf co-catalyst.

  的TiCl 4 /卜3 Ñ进行不同酮类之间和酮和醛，在良好的以高优异的产率之间高效交叉醛醇添加顺-stereoselectivities。此外，TiCl 4 / Bu 3 N与0.05当量的TMSOTf助催化剂还促进了甲酯之间的直接Claisen缩合反应。
• STANNOUS TRIFLATE: A NEW ALDOL REACTION VIA DIVALENT TIN ENOLATES
  作者：Teruaki Mukaiyama、Rodney. W. Stevens、Nobuharu Iwasawa

  DOI：10.1246/cl.1982.353

  日期：1982.3.5

  Divalent tin enolates formed from stannous triflate and ketones react with carbonyl compounds under mild conditions to give the corresponding aldol products in good yields. In the case of cross-cou...

  由三氟甲磺酸亚锡和酮形成的二价锡烯醇化物在温和条件下与羰基化合物反应，以良好的产率得到相应的醛醇产物。在交叉的情况下...