(S)-2,2'-dihydroxy-3,3'-dimethyl-5,5',6,6',7,7',8,8'-octahydro-1,1'-dinaphthyl | 1018785-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (S)-2,2'-dihydroxy-3,3'-dimethyl-5,5',6,6',7,7',8,8'-octahydro-1,1'-dinaphthyl
• 英文别名: (S)-3,3'-dimethyl-5,5',6,6',7,7',8,8'-octahydro-[1,1'-binaphthalene]-2,2'-diol；(S)-3,3'-dimethyl-5,6,7,8,5',6,',7',8'-octahydro[1,1']binaphthalenyl-2,2'-diol；1-(2-Hydroxy-3-methyl-5,6,7,8-tetrahydronaphthalen-1-yl)-3-methyl-5,6,7,8-tetrahydronaphthalen-2-ol
• CAS: 1018785-59-5
• 化学式: C₂₂H₂₆O₂
• 分子量: 322.447
• InChiKey: ZKAPPWYNZSKUFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 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)-2,2'-dihydroxy-3,3'-dimethyl-5,5',6,6',7,7',8,8'-octahydro-1,1'-dinaphthyl 以70%的产率得到
  参考文献：
  名称：

  CRAM D. J.; HELGESON R. C.; PEACOCK S. C.; KAPLAN L. J.; DOMEIER L. A.; M+, J. ORG. CHEM., 1978, 43, NO 10, 1930-1946

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-3,3'-dimethyl-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 在 盐酸 、 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 70.0~90.0 ℃ 、9.0 MPa 条件下， 反应 15.0h， 生成 (S)-2,2'-dihydroxy-3,3'-dimethyl-5,5',6,6',7,7',8,8'-octahydro-1,1'-dinaphthyl
  参考文献：
  名称：

  手性BINOLs的镁配合物催化的格氏试剂对醛的对映选择性乙烯基化。

  摘要：

  醛类的直接催化不对称格氏反应和乙烯基格林纳德试剂对醛的对映选择性乙烯基化是一个长期的挑战。这项工作表明，（S）-3,3'-二甲基双酚镁对映体选择性地通过双（2- [ N，N'-二甲基氨基]乙基）醚（BDMAEE）与失活的乙烯基溴化镁对醛进行直接乙烯基化。添加正丁基氯化镁。迄今为止，达到了63％的最高ee。

  DOI：

  10.1002/chir.23038

文献信息

• Copper-catalyzed enantioselective conjugate addition of Grignard reagents to acyclic enones using monodentate phosphoramidite ligands
  作者：Beatriz Maciá、M. Ángeles Fernández-Ibáñez、Nataša Mršić、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1016/j.tetlet.2008.01.019

  日期：2008.3

  Herein, we report efficient catalysts based on phosphoramidites for the asymmetric copper-catalyzed conjugate addition of Grignard reagents to acyclic α,β-unsaturated ketones. A variety of Grignard reagents can be added to aliphatic and aromatic acyclic enones with good yields and moderate to good enantioselectivities.

  在此，我们报道了基于亚磷酰胺的高效催化剂，用于将格氏试剂不对称铜催化的共轭加成到无环α，β-不饱和酮上。可以将各种格氏试剂以良好的产率和中等至良好的对映选择性加入脂族和芳族无环烯酮中。
• PROCESS FOR PREPARING TETRAHYDROQUINOLINE DERIVATIVES
  申请人：Okamoto Masaki

  公开号：US20090292125A1

  公开（公告）日：2009-11-26

  The present invention is to provide a process for preparing optically active tetrahydroquinoline derivatives which can be used for the treatment and/or prevention of diseases such as arteriosclerotic diseases, dyslipidemia and the like, and a process for preparing synthetic intermediates thereof. Specifically, (2R,4S)-2-ethyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinolin-4-ylamine or a salt thereof is prepared with fewer steps without using an optical resolution, and the optically active tetrahydroquinoline derivatives are obtained from the amine compound.

  本发明提供了一种制备光学活性四氢喹啉衍生物的方法，该方法可用于治疗和/或预防动脉硬化性疾病、血脂异常等疾病，以及其合成中间体的制备方法。具体而言，本发明通过少量步骤制备(2R,4S)-2-乙基-6-三氟甲基-1,2,3,4-四氢喹啉-4-胺或其盐，而不使用光学分辨，并从胺化合物中获得光学活性四氢喹啉衍生物。
• Cobalt-Catalyzed Enantioselective Directed C–H Alkylation of Indole with Styrenes
  作者：Pin-Sheng Lee、Naohiko Yoshikai

  DOI：10.1021/ol503119z

  日期：2015.1.2

  A cobalt-chiral phosphoramidite catalyst promotes enantioselective imine-directed C2-alkylation of Boc-protected indoles with styrenes. The reaction affords 1,1-diarylethane products in moderate to good yields with good enantioselectivities under mild conditions. A deuterium-labeling experiment suggests that the enantioselectivity is controlled by both the styrene insertion and the C-C reductive elimination steps.
• A simple and highly effective method for hydrogenation of arenes by [Rh(COD)Cl]2
  作者：Da-Wei Wang、Sheng-Mei Lu、Yong-Gui Zhou

  DOI：10.1016/j.tetlet.2008.12.108

  日期：2009.3

  Hydrogenation of arenes, including chiral BINOLs and the lignin model compounds, has been achieved efficiently by using the simple complex [Rh(COD)Cl](2) as catalyst precursor. (C) 2009 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Desymmetrization of Silacyclobutanes with Alkynes: Enantioselective Synthesis of Silicon-Stereogenic 1-Sila-2-cyclohexenes and Mechanistic Considerations
  作者：Ryo Shintani、Kohei Moriya、Tamio Hayashi

  DOI：10.1021/ol301191u

  日期：2012.6.1

  A palladium-catalyzed enantioselective desymmetrization of silacyclobutanes with alkynes has been developed to give silicon-stereogenic 1-sila-2-cyclohexenes with high enantioselectivity. The products thus obtained undergo further derivatizations with complete stereoselectivity, and a new catalytic cycle involving alkyne coordination (oxidative cyclization)-transmetalation (sigma-bond metathesis)-reductive elimination has also been proposed.