(R)-1-phenylundecan-1-ol

• 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: (R)-1-phenylundecan-1-ol
• 英文别名: (1R)-1-phenylundecan-1-ol
• 化学式: C₁₇H₂₈O
• 分子量: 248.409
• InChiKey: CYEZIZHBBKGLCX-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  (R)-1-phenylundecan-1-ol 在 bis(2-methoxyethyl) azodicarboxylate 、 4-二苯基膦苯甲酸 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以99%的产率得到(S)-1-phenyl-1-undecanol
  参考文献：
  名称：

  Mitsunobu Reaction with 4-(Diphenylphosphino)benzoic Acid: A Separation-Friendly Bifunctional Reagent that Serves as Both a Reductant and a Pronucleophile

  摘要：

  4-(Diphenylphosphino)benzoic acid was used for the Mitsunobu reaction as a bifunctional reagent that served as both a reductant and a pronucleophile. When combined with di-2-methoxyethyl azodicarboxylate, inversion of a secondary alcohol stereospecifically occurred to give an ester carrying a phosphine oxide group. The reaction mixture was directly hydrolyzed to give an inverted secondary alcohol in sufficient stereo and chemical purities by the presently developed chromatography-free process in conjunction with basic extraction, drying, and concentration.

  DOI：

  10.1055/s-0032-1318327
• 作为产物：
  描述：

  十一烷醇 在 (R)-Me-BIPAM 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 acetonitrile(cyclopentadienyl)[2-(di-i-propylphosphino)-4-(t-butyl)-1-methyl-1H-imidazole]ruthenium(II) hexafluorophosphate 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 12.0h， 生成 (R)-1-phenylundecan-1-ol
  参考文献：
  名称：

  一锅立体选择性合成仲苄醇的多催化方法

  摘要：

  一锅法有可能迅速建立分子的复杂性，而无需分离和纯化连续的中间体。在这里，我们报告了多催化方案，该方案在顺序催化下将烯烃，不饱和脂族醇和芳基硼酸转化为具有高立体选择性（通常> 95：5 er）的仲苄醇，该催化集成了烯烃的交叉复分解，异构化和亲核加成反应。前手性烯丙醇可以高立体选择性（> 98：2 er，> 20：1 dr）转化为产品的任何立体异构体。

  DOI：

  10.1021/acs.orglett.1c00939

文献信息

• Recyclable Mn(I) Catalysts for Base‐Free Asymmetric Hydrogenation: Mechanistic, DFT and Catalytic Studies
  作者：Harikrishnan Jayaprakash、Peter Coburger、Michael Wörle、Antonio Togni、Hansjorg Grützmacher

  DOI：10.1002/chem.202201522

  日期：2022.8.22

  Mechanistic and DFT studies on a series of recyclable Mn(I) complexes disclosed six vital factors determining their activities along with the existence of different mechanisms for asymmetric direct and transfer hydrogenations. Moreover, Mn(I) complex 2 b (cat. loading: 0.4-1 mol%) performs base-free transfer hydrogenation of alkyl ketones ketones with enantioselectivity up to 98 %. More significantly

  对一系列可回收 Mn(I) 配合物的机理和 DFT 研究揭示了决定其活性的六个重要因素，以及不对称直接和转移氢化的不同机制的存在。此外，Mn(I)配合物2b（催化剂负载量：0.4-1 mol%）对烷基酮酮进行无碱转移氢化，对映选择性高达 98%。更重要的是，已经发现了一种新颖且简单的单步工艺，用于从催化剩余物中回收剩余物质。
• Highly enantioselective dynamic kinetic resolution of alkyl aryl carbinols carrying a trimethylsilyl group with a highly active lipoprotein lipase preparation
  作者：Jeonghun Cho、Jusuk Lee、Jaiwook Park、Mahn-Joo Kim

  DOI：10.1016/j.tetasy.2015.06.010

  日期：2015.8

  The kinetic and dynamic kinetic resolution of alkyl aryl carbinols carrying a trimethylsilyl group with a highly active lipase preparation containing lipoprotein lipase, dextrin, and ionic surfactant 1 has been explored. It was found that all the trimethylsilyl-containing substrates were accepted by lipoprotein lipase-dextrin 1 (LPL-D1) with perfect enantioselectivity (E = >200). As a result, the dynamic kinetic resolution of these substrates with LPL-D1 in the presence of a Ru-based racemization catalyst provided single enantiomeric products (>99% ee) with good yields. Furthermore, the dynamic kinetic resolution products were readily desilylated or halodesilylated to yield enantiopure alkyl aryl carbinols. Thus a useful protocol for the highly enantioselective synthesis of alkyl aryl carbinols, particularly those carrying a long alkyl chain (C-6-C-10) has been established. (C) 2015 Elsevier Ltd. All rights reserved.
• Enantioselective Alkylation of Aldehydes with Chiral Organomagnesium Amides (COMAs)
  作者：Kelvin H. Yong、Nicholas J. Taylor、J. Michael Chong

  DOI：10.1021/ol0258132

  日期：2002.10.1

  [GRAPHICS]Dialkylmagnesiums react with chiral secondary amines to form chiral organomagnesium amides (COMAs). These reagents alkylate aldehydes to form secondary alcohols with enantioselectivities up to 91:9 er.
• Mitsunobu Reaction with 4-(Diphenylphosphino)benzoic Acid: A Separation-Friendly Bifunctional Reagent that Serves as Both a Reductant and a Pronucleophile
  作者：Takashi Sugimura、Natsuko Muramoto、Kazuki Yoshino、Tomonori Misaki

  DOI：10.1055/s-0032-1318327

  日期：——

  4-(Diphenylphosphino)benzoic acid was used for the Mitsunobu reaction as a bifunctional reagent that served as both a reductant and a pronucleophile. When combined with di-2-methoxyethyl azodicarboxylate, inversion of a secondary alcohol stereospecifically occurred to give an ester carrying a phosphine oxide group. The reaction mixture was directly hydrolyzed to give an inverted secondary alcohol in sufficient stereo and chemical purities by the presently developed chromatography-free process in conjunction with basic extraction, drying, and concentration.
• Multicatalytic Approach to One-Pot Stereoselective Synthesis of Secondary Benzylic Alcohols
  作者：Alessandra Casnati、Dawid Lichosyt、Bruno Lainer、Lukas Veth、Paweł Dydio

  DOI：10.1021/acs.orglett.1c00939

  日期：2021.5.7

  convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).

  一锅法有可能迅速建立分子的复杂性，而无需分离和纯化连续的中间体。在这里，我们报告了多催化方案，该方案在顺序催化下将烯烃，不饱和脂族醇和芳基硼酸转化为具有高立体选择性（通常> 95：5 er）的仲苄醇，该催化集成了烯烃的交叉复分解，异构化和亲核加成反应。前手性烯丙醇可以高立体选择性（> 98：2 er，> 20：1 dr）转化为产品的任何立体异构体。