(S,S)-dicyclohexylbut-2-yne-1,4-diol | 188533-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S,S)-dicyclohexylbut-2-yne-1,4-diol
• 英文别名: (1S,4S)-1,4-dicyclohexylbut-2-yne-1,4-diol
• CAS: 188533-48-4
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: XPFSGHNYNKITHN-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S,S)-dicyclohexylbut-2-yne-1,4-diol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 [(E,1S,4S)-1,4-dicyclohexyl-4-[(4-methylphenyl)sulfonylcarbamoyloxy]but-2-enyl] N-(4-methylphenyl)sulfonylcarbamate
  参考文献：
  名称：

  Stereodivergent Approach to β-Hydroxy α-Amino Acids from C₂-Symmetrical Alk-2-yne-1,4-diols

  摘要：

  [GRAPHICS]A new stereodivergent route to erythro- and threo-beta-substituted serines from a common G-symmetrical alk-2-yne-1,4-diol is described. Stereocontrol in such an acyclic system is achieved by taking advantage of symmetry. Stereoselective alkyne reduction to either (Z)- or (E)-olefin allows selection of the stereochemistry of cc-carbon in the final amino acid by using a Pd(0)-catalyzed process. This strategy has been applied to the synthesis of (2S,3S)-3-hydroxyleucine.

  DOI：

  10.1021/ol0270428
• 作为产物：
  描述：

  1,4-dicyclohexylbut-2-yne-1,4-diol 在 chromium(VI) oxide 、 dicobalt octacarbonyl 、 硫酸 作用下， 以 二氯甲烷 、 水 、 丙酮 、 正戊烷 为溶剂， 反应 1.0h， 生成 (S,S)-dicyclohexylbut-2-yne-1,4-diol
  参考文献：
  名称：

  恶唑硼烷介导的Alk-2-yne-1,4-二酮的还原对Alk-2-yne-1,4-二醇的立体选择性方法†

  摘要：

  我们在恶唑硼烷（R）-6存在下进行了硼烷介导的一系列对称的alk-2-yne-1,4-diones（5）的硼烷介导还原反应，得到（R，R）-alk-2-yne -1,4-二醇（（R，R）-1）收率高，立体选择性高（ee高达99.9％）。在某些情况下，可通过两步过程提高1的立体化学纯度：（i）将1暂时转化为其vic -dibromo衍生物9，这使我们能够除去次要内消旋体通过色谱分离异构体，和（ii）用SmI 2再生对映体富集的二醇1。由5衍生的六羰基二钴络合物8的还原也是成功的。

  DOI：

  10.1021/jo0495687

文献信息

• Stereoselective reduction of unsaturated 1,4-diketones. A practical route to chiral 1,4-diols
  作者：Jordi Bach、Ramon Berenguer、Jordi Garcia、Teresa Loscertales、Judith Manzanal、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(96)02476-8

  日期：1997.2

  synthetic route to C2-symmetric chiral 1,4-diols based on the borane-mediated oxazaborolidine-catalysed reduction of 2-ene-1,4-diones (2), of 2-yne-1,4-diones (3), and/or of Co-complexed diketones 4 is described. Good to excellent enantio- and diastereoselectivities have been obtained in the reduction of diketones 3 and 4, catalysed by oxazaborolidines 6 and 5, respectively.

  基于硼烷介导的恶唑硼烷催化的2-烯-1,4-二酮（2），2-炔-1,4-二酮（2）还原反应的合成C 2对称手性1,4-二醇的新合成路线描述3）和/或共络二酮4。对二酮3和4的还原分别获得了良好或优异的对映异构和非对映异构选择性，分别由恶唑硼烷6和5催化。
• Stereoselective approach to alk-2-yne-1,4-diols. Application to the synthesis of musclide B
  作者：Marta Amador、Xavier Ariza、Jordi Garcia、Jordi Ortiz

  DOI：10.1016/s0040-4039(02)00395-7

  日期：2002.4

  An expedient method for the stereoselective preparation of alk-2-yne-1,4-diols has been achieved, based on the addition of chiral alk-1-yn-3-ols (or their protected derivatives) to aldehydes mediated by zinc triflate, Et3N, and (+)- or (–)-N-methylephedrine. In general, the configuration observed at the emergent stereocenter depends on the N-methylephedrine employed resulting in good to excellent

  基于将手性烷基-1-yn-3-醇（或其受保护的衍生物）添加到由三氟甲磺酸锌介导的醛中，已经实现了一种立体选择性制备alk-2-yne-1,4-二醇的简便方法，Et 3 N和（+）-或（–）- N-甲基麻黄碱。通常，在新兴的立体中心观察到的构型取决于所使用的N-甲基麻黄碱，从而导致良好的非对映选择性。该策略已应用于对麝香的生物活性代谢产物B的对映选择性合成。
• Preparation and use of diols
  申请人：——

  公开号：US20040143143A1

  公开（公告）日：2004-07-22

  A process for the preparation of diols by a Lewis acid-catalysed aldehyde addition reaction on hydroxyalkynes followed by hydrogenation is described. The process provides a wide range of diols from simple, readily available starting materials. In particular the process is suitable for preparing chiral 1,4-diols suitable for the preparation of chiral phospholane ligands for use in asymmetric catalysis.

  本文介绍了一种通过路易斯酸催化的羟基炔醛加成反应制备二元醇，然后进行氢化的工艺。该工艺可利用简单易得的起始原料制备多种二元醇。该工艺尤其适用于制备手性 1,4 二醇，适合制备用于不对称催化的手性磷烷配体。
• Regio- and stereoselective microwave-assisted synthesis of 5-alkyl-4-alkenyl-4-phenyl-1,3-oxazolidin-2-ones
  作者：Marta Amador、Xavier Ariza、Jérémie Boyer、Lucia D’Andrea、Jordi Garcia、Jaume Granell

  DOI：10.1016/j.tetlet.2009.12.036

  日期：2010.2

  Chiral symmetrical alk-2-yne-1,4-diols have been stereoselectively transformed into 5-alkyl-4-alkenyl-4-phenyl-1,3-oxazolidin-2-ones, which are precursors of quaternary alpha-amino beta-hydroxy acids. The key step was the cyclization of the bis(tosylcarbamates) of 2-phenylalk-2-yne-1,4-diols, easily obtained from the starting chiral diols. These cyclizations were accomplished with complete regioselectivity and up to 92:8 dr in the presence of catalytic amounts of Ni(0) or Pd (II) derivatives under microwave heating. (C) 2009 Elsevier Ltd. All rights reserved.
• PREPARATION AND USE OF DIOLS
  申请人：JOHNSON MATTHEY PUBLIC LIMITED COMPANY

  公开号：EP1389174A1

  公开（公告）日：2004-02-18