3-hydroxy-2-methyl-1,5-diphenylpentan-1-one | 73739-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-2-methyl-1,5-diphenylpentan-1-one
• 英文别名: (2R,3R)-3-hydroxy-2-methyl-1,5-diphenylpentan-1-one
• CAS: 73739-38-5
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: AAIOCDMNRHKNRK-RHSMWYFYSA-N

物化性质

• 沸点：
  442.6±38.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-iodo-1-phenylpropan-1-one 在 2,6-二甲基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 3-hydroxy-2-methyl-1,5-diphenylpentan-1-one
  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

• 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。
• Method for Performing Aldol Reaction in Water
  申请人：Kobayashi Shu

  公开号：US20070238902A1

  公开（公告）日：2007-10-11

  An aldol reaction in an aqueous solution between an aldehyde represented by the following formula (I): R—CHO  (I) (wherein R is a hydrocarbon group which may have an substituent), and a silicon enolate represented by the following formula (II): (wherein R 1 and R 2 are a hydrogen atom or an aliphatic hydrocarbon group, at least one of them being an aliphatic hydrocarbon group; and R 3 is a substituent selected from the group consisting of an aliphatic hydrocarbon group, an aromatic hydrocarbon group and a sulfur-containing substituent, wherein R 2 and R 3 may be combined with each other to form a ring) is performed so as to generate diastereoselectivity by using FeCl 3 , which is a low-cost Lewis acid, and a surfactant.

  在水溶液中进行的醛缩反应，其中一个醛以以下式表示：R—CHO (I)（其中R是一个可能带有取代基的碳氢基团），另一个是以以下式表示的硅烯醇：（式中R1和R2是氢原子或脂肪烃基团，至少一个是脂肪烃基团；R3是从脂肪烃基团、芳香烃基团和含硫取代基组成的群中选择的取代基，其中R2和R3可以结合在一起形成环），通过使用FeCl3（一种低成本的Lewis酸）和表面活性剂来产生对映选择性。
• Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9‐BBN‐Derived Ate Complexes
  作者：Chunyin Law、Yan Meng、Seung Moh Koo、James P. Morken

  DOI：10.1002/anie.201901927

  日期：2019.5.13

  β-Boryl carbonyl compounds are produced by a Ni-catalyzed cross-coupling of vinylboron "ate" complexes and acid chloride or acid anhydride electrophiles. The reactions are efficient, being complete in as little as two minutes, and can be applied to a broad range of substrates.

  β-硼基羰基化合物是通过乙烯基硼“ate”络合物和酰基氯或酸酐亲电子试剂的镍催化交叉偶联产生的。该反应非常高效，仅需两分钟即可完成，并且可应用于多种基材。
• Diastereoselective Aldol Reaction of<i>α</i>-Bromo Ketones with Aliphatic Aldehydes by Using Titanium(II) Chloride and Copper
  作者：Teruaki Mukaiyama、Akifumi Kagayama、Koji Igarashi、Isamu Shiina

  DOI：10.1246/cl.1999.1157

  日期：1999.11

  Highly diastereoselective aldol reaction of α-bromo ketones with aliphatic aldehydes was successfully carried out by using titanium(II) chloride and copper in dichloromethane at low temperature. Similarly, Reformatsky-type reaction of α-bromo thioester with aliphatic aldehydes was promoted under mild conditions to afford β-hydroxy thioesters in good to moderate yields.

  通过在二氯甲烷中使用氯化钛（II）和铜，在低温下成功地进行了α-溴酮与脂肪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 型反应在温和条件下得到促进，以良好到中等的产率得到 β-羟基硫酯。
• Stereoselective Crossed Aldol Reaction via Boron Enolate Generated from α-Iodoketones and 9-BBN-H
  作者：Teruaki Mukaiyama、Shouhei Imachi、Keiko Yamane、Masahiro Mizuta

  DOI：10.1246/cl.2002.698

  日期：2002.7

  Boron enolates were in situ generated smoothly by treating α-iodo ketones with 9-BBN-H, and aldols were produced in highly diastereoselective manner by successive reaction with various aldehydes at low temperature.

  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。