5-hydroxy-4-methyl-7-phenylheptan-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-hydroxy-4-methyl-7-phenylheptan-3-one
• 英文别名: (4S*,5R*)-5-Hydroxy-4-methyl-7-phenyl-3-heptanone；(4S,5R)-5-hydroxy-4-methyl-7-phenylheptan-3-one
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: QYQFMLOZMVEXEA-BXUZGUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-methyl-7-phenylheptan-3-one 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 24.0h， 生成 (4R*,5S*,6R*)-4-(2-Cyanoethyl)-4-ethyl-5-methyl-2-phenyl-6-(2-phenylethyl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  Hydroxyl-Directed Intermolecular Ketone-Olefin Couplings Promoted by SmI2

  摘要：

  SmI2-promoted intermolecular ketone-olefin couplings are facilitated and stereocontrolled by hydroxyl groups incorporated within the starting materials. For example, the SmI2-induced ketone - olefin coupling reactions of alpha-hydroxy ketone 5 with ethyl acrylate, acrylonitrile, ethyl crotonate, and 2(5 H)-furanone proceeded with high stereocontrol to afford the syn-1,2-diol products 6-9 in good yields. Excellent diastereoselectivity was achieved in the reductive couplings of beta-hydroxy aldehyde 21 and erythro-beta-hydroxy ketone 24 with acrylonitrile using SmI2, to produce the anti-1,3-diols 22 and 25 in good yields. The sense of the stereo-selectivity was in full accord with a chelation-control model. In the proposed model, the stereochemistry of the reaction product is explained by assuming that a cyclic ketyl radical is generated during the initial single-electron reduction by SmI2. This radical species results from the chelation of the Sm-III cation, attached to the ketyl radical, with the hydroxyl group.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3252::aid-chem3252>3.0.co;2-d
• 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-methyl-7-phenylheptan-3-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 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 Enolates Generated from α-Iodo Ketones and 9-Borabicyclo[3.3.1]nonane
  作者：Teruaki Mukaiyama、Tomofumi Takuwa、Keiko Yamane、Shouhei Imachi

  DOI：10.1246/bcsj.76.813

  日期：2003.4

  2-iodo-1-(4-methoxyphenyl)propan-1-one, 2-iodopentan-3-one, 2-iodo-2-methyl-1-phenylpropan-1-one, 3,4-dihydro-2-iodo-1(2H)-naphthalenone, 2-iodo-1-phenylethan-1-one and 1-iodo-4-phenylbutan-2-one with 9-borabicyclo[3.3.1]nonane (9-BBN). Aldols were produced in good yields with good to high diastereoselectivities by subsequent reaction of boron enolates thus formed with various aldehydes. Several boron enolates derived

  硼烯醇化物是通过处理各种 α-碘酮如 2-iodo-1-phenylpropan-1-one、2-iodo-1-(4-methoxyphenyl)propan-1-one、2-iodopentan- 3-one, 2-iodo-2-methyl-1-phenylpropan-1-one, 3,4-dihydro-2-iodo-1(2H)-naphthalenone, 2-iodo-1-phenylethan-1-one 和 1 -iodo-4-phenylbutan-2-one 与 9-borabicyclo[3.3.1]nonane (9-BBN)。通过由此形成的硼烯醇化物与各种醛的后续反应，以良好的收率和良好至高的非对映选择性生产了羟醛。通过蒸馏成功分离了几种衍生自 α-碘酮和频哪醇硼烷的硼烯醇化物，但产率相当适中。
• Chiral Lewis Acid Catalysis in Aqueous Media. Catalytic Asymmetric Aldol Reactions of Silyl Enol Ethers with Aldehydes in a Protic Solvent Including Water
  作者：Shu Kobayashi、Satoshi Nagayama、Tsuyoshi Busujima

  DOI：10.1246/cl.1999.71

  日期：1999.1

  Chiral copper(II)-catalyzed asymmetric aldol reactions of silyl enol ethers with aldehydes have been successfully carried out in a water-ethanol solution. The use of the protic solvent including wa...

  手性铜 (II) 催化的甲硅烷基烯醇醚与醛的不对称羟醛反应已在水-乙醇溶液中成功进行。使用质子溶剂包括水...
• Scandium trisdodecylsulfate (STDS). A new type of lewis acid that forms stable dispersion systems with organic substrates in water and accelerates aldol reactions much faster in water than in organic solvents
  作者：Shū Kobayashi、Takeshi Wakabayashi

  DOI：10.1016/s0040-4039(98)01081-8

  日期：1998.7

  A new type of Lewis acid, scandium trisdodecylsulfate (STDS), was prepared. In the presence of a catalytic amount of STDS, aldol reactions of silyl enol ethers with aldehydes proceeded smoothly in water without using any organic solvents. It was proven that stable dispersion systems including the catalyst and organic substrates were formed in water and that catalytic activity in water was much higher

  制备了一种新型的路易斯酸，三十二烷基硫酸scan（STDS）。在催化量的STDS的存在下，在不使用任何有机溶剂的情况下，甲硅烷基烯醇醚与醛的醛醇缩合反应在水中顺利进行。事实证明，在水中形成了稳定的分散体系，包括催化剂和有机底物，在水中的催化活性远高于在有机溶剂中的催化活性。据我们所知，这是路易斯酸在水中稳定分散体系中催化的第一个例子。
• Uncatalyzed aldol reaction using a dimethylsilyl enolate and α-dimethylsilyl ester in N,N-dimethylformamide
  作者：Katsukiyo Miura、Hiroshi Sato、Kentaro Tamaki、Hajime Ito、Akira Hosomi

  DOI：10.1016/s0040-4039(98)00275-5

  日期：1998.4

  Dimethylsilyl enolates and alpha-dimethylsilyl esters reacted with aldehydes in N,N-dimethyl-formamide without an activator to give aldol adducts in moderate to good yields. Under the same conditions, the corresponding trimethylsilyl derivatives exhibited lower reactivities toward the aldol reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.