(R)-(+)-1-phenyl-1-nonanol | 131320-86-0

• 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-phenyl-1-nonanol
• 英文别名: (R)-1-phenyl-1-nonanol；(R)-1-phenylnonan-1-ol；(1R)-1-phenylnonan-1-ol
• CAS: 131320-86-0
• 化学式: C₁₅H₂₄O
• 分子量: 220.355
• InChiKey: KBXJSWRVYBTZPC-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  正辛基镁溴盐 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 93.0h， 生成 (R)-(+)-1-phenyl-1-nonanol
  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 preparation of sec. Alcohols from aldehydes and dialkyl zinc compounds, generated in situ from Grignard reagents, using substoichiometric amounts of TADDOL-titanates
  作者：Joanna Linda von dem Bussche-Hünnefeld、Dieter Seebach

  DOI：10.1016/0040-4020(92)80023-9

  日期：1992.7

  the Schlenk trick (precipitation of MgX2 from ethereal solutions by the addition of 1,4-dioxane) mixtures of a Grignard reagent RMgX (X = Cl, Br, I) and 0.5 equiv. ZnCl2 in Et2O can be converted to zinc alkyls R2Zn which in turn are added with enantio-selectivities of up to 99 : 1 to aliphatic and aromatic aldehydes in the presence of Ti(OCHMe2)4 and a chiral titanate derived from an α,α,α′,α′-tetraaryl-1

  使用Schlenk技巧（通过添加1,4-二恶烷，从醚溶液中沉淀出MgX 2），将格氏试剂RMgX（X = Cl，Br，I）和0.5当量的混合物。可以将Et 2 O中的ZnCl 2转化为烷基锌R 2 Zn，然后在Ti（OCHMe 2）4和手性钛酸酯的存在下，将脂族和芳族醛的对映选择性高达99：1。由α，α，α'，α'-四芳基-1,3-二氧戊环-4,5-二甲醇（TADDOL）制得。格氏试剂盒也可以使用双键，苯环或缩醛基。比较了不同的TADDOL在这类对映选择性反应中的用途。
• A new preparation of diorganozincs from olefins via a nickel catalyzed hydrozincation
  作者：Stephan Vettel、Andrea Vaupel、Paul Knochel

  DOI：10.1016/0040-4039(94)02438-h

  日期：1995.2

  The reaction of olefins with diethylzinc in the presence of catalytic amounts of Ni(acac)2 provides dialkylzincs (neat, 40–50 °C, 2–6 h). These zinc reagents can be trapped by various electrophiles or used for the catalytic asymmetric addition to aldehydes (> 85 % ee). Allylic and homoallylic alcohols are especially good substrates for the reaction.

  在催化量的Ni（acac）2存在下，烯烃与二乙基锌反应生成二烷基锌（纯净，40–50°C，2–6 h）。这些锌试剂可以被各种亲电试剂捕获，或用于催化不对称加成醛（> 85％ee）。烯丙基和均烯丙基醇是该反应的特别好的底物。
• Ru/Me-BIPAM-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes and α-Ketoesters
  作者：Yasunori Yamamoto、Tomohiko Shirai、Momoko Watanabe、Kazunori Kurihara、Norio Miyaura

  DOI：10.3390/molecules16065020

  日期：——

  A ruthenium-catalyzed asymmetric arylation of aliphatic aldehydes and α-ketoesters with arylboronic acids has been developed, giving chiral alkyl(aryl)methanols and α-hydroxy esters in good yields. The use of a chiral bidentate phosphoramidite ligand (Me-BIPAM) achieved excellent enantioselectivities.

  已经开发了钌催化的脂肪醛和α-酮酯与芳基硼酸的不对称芳基化，以良好的产率得到手性烷基（芳基）甲醇和α-羟基酯。手性双齿亚磷酰胺配体 (Me-BIPAM) 的使用实现了出色的对映选择性。
• Enantioselective Hydrogenation of Aromatic Ketones Catalyzed by Ru Complexes of Goodwin−Lions-type sp²N/sp³N Hybrid Ligands R-BINAN-R‘-Py
  作者：Hanmin Huang、Tomoko Okuno、Kazuomi Tsuda、Masahiro Yoshimura、Masato Kitamura

  DOI：10.1021/ja062451a

  日期：2006.7.1

  Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R'-Py possessing a C2 axis binaphthyl skeleton have been designed and synthesized. Combination of the new non-phosphine ligand with Ru(pi-CH2C(CH3)CH2)2(cod) has been revealed to catalyze the hydrogenation of aromatic ketones with high enantioselectivity of up to 99% ee. The reaction proceeds essentially without the need for any bases, but the reactivity is enhanced by the addition of KOt-C4H9 attaining an S/C ratio of up to 10 000. The success should expand the range of possibilities in designing catalysts not only for hydrogenation but also for many other reactions.
• Synthesis of homochiral β-hydroxy-α-aminoacids [(2S,3R,4R)-3,4-dihydroxyproline and (2S,3R,4R)-3,4-dihydroxypipecolic aicd] and of 1,4-dideoxy-1,4-imino-D-arabinitol [DAB1] and fagomine [1,5-imino-1,2,5-trideoxy-D-arabino-hexitol]
  作者：George W.J. Fleet、David R. Witty

  DOI：10.1016/s0957-4166(00)86337-5

  日期：1990.1