(R)-1-(4-chlorophenyl)heptan-1-ol | 1448775-57-2

• 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: (R)-1-(4-chlorophenyl)heptan-1-ol
• 英文别名: (1R)-1-(4-chlorophenyl)heptan-1-ol
• CAS: 1448775-57-2
• 化学式: C₁₃H₁₉ClO
• 分子量: 226.746
• InChiKey: LJUMUOIYYHZFOC-CYBMUJFWSA-N

物化性质

• 沸点：
  323.1±17.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(4-bromophenyl)heptan-1-ol 在 N-氯代丁二酰亚胺 、 正丁基锂 、 (OC)2ClRu(C₅(C₆H₄OCH₃)4OOCC₆H₄OCH₃) 、 potassium chloride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 53.0h， 生成 (R)-1-(4-chlorophenyl)heptan-1-ol
  参考文献：
  名称：

  Highly enantioselective dynamic kinetic resolution of alkyl aryl carbinols carrying a trimethylsilyl group with a highly active lipoprotein lipase preparation

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2015.06.010

文献信息

• Enantioselective Alkylation of Aldehydes Using Functionalized Alkylboron Reagents Catalyzed by a Chiral Titanium Complex
  作者：Ravindra Kumar、Hiroki Kawasaki、Toshiro Harada

  DOI：10.1021/ol4019248

  日期：2013.8.16

  A practical method is developed for the synthesis of enantioenriched functionalized secondary alcohols through catalytic enantioselective alkylation of aldehydes. Functionalized alkylboron reagents, [FG–(CH2)n]3B (FG = Br, TIPSO, PhtN, CO2iPr, and CN) prepared from terminal olefin precursors by hydroboration, undergo enantioselective addition to aldehydes in the presence of a catalytic amount (5 mol

  开发了一种通过醛的催化对映选择性烷基化合成富含对映体的官能化仲醇的实用方法。通过氢硼化从末端烯烃前体制备的功能化烷基硼试剂[FG–（CH 2）n ] 3 B（FG = Br，TIPSO，PhtN，CO 2 i Pr和CN），在存在a的情况下对醛进行对映选择性加成。催化量（5mol％）的3-（3，5-二苯基苯基）-H 8 -BINOL和过量的四异丙氧基钛，以高达99％ee的高对映选择性提供相应的官能化醇。
• Catalytic Enantioselective Addition of Organozirconium Reagents to Aldehydes
  作者：Ricard Solà、Marcos Veguillas、María González-Soria、Nicholas Carter、M. Fernández-Ibáñez、Beatriz Maciá

  DOI：10.3390/molecules23040961

  日期：——

  A catalytic enantioselective addition reaction of alkylzirconium species to aromatic aldehydes is reported. The reaction, facilitated by a chiral nonracemic diol ligand complex with Ti(OiPr)4, proceeds under mild and convenient conditions, and no premade organometallic reagents are required since the alkylzirconium nucleophiles are generated in situ by hydrozirconation of alkenes with the Schwartz

  报道了烷基锆物种与芳香醛的催化对映选择性加成反应。该反应由手性非外消旋二醇配体与 Ti(OiPr)4 配合物促进，在温和方便的条件下进行，并且不需要预制的有机金属试剂，因为烷基锆亲核试剂是通过烯烃与 Schwartz 试剂的氢化锆化原位生成的。该方法与功能化亲核试剂和广泛的芳香醛兼容。
• Ru-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes via P-Chiral Monophosphorous Ligands
  作者：Rui Miao、Yanping Xia、Yifei Wei、Lu Ouyang、Renshi Luo

  DOI：10.3390/molecules27123898

  日期：——

  situ was found to promote an enantioselective addition of aliphatic aldehydes with arylboronic acids, delivering the chiral alcohols in excellent yields and enantioselectivities and exhibiting a broad scope of aliphatic aldehydes and arylboronic acids. The enantioselectivities are highly dependent on the monophosphorous ligands. The utility of this asymmetric synthetic method was showcased by a large-scale

  手性醇在精细化学品、医药和农用化学品中应用最为广泛。在此，发现原位形成的钌-单膦催化剂可促进脂肪醛与芳基硼酸的对映选择性加成，以优异的产率和对映选择性提供手性醇，并表现出广泛的脂肪醛和芳基硼酸范围。对映选择性高度依赖于单磷配体。通过大规模改造展示了这种不对称合成方法的实用性。
• 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.