(R)-(+)-1,1'-binaphthalene-2,2'-diyl O,O-bis(N,N-dimethylthiocarbamate) | 189084-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-(+)-1,1'-binaphthalene-2,2'-diyl O,O-bis(N,N-dimethylthiocarbamate)
• 英文别名: <1,1'-Binaphthalene>-2,2'-diyl O,O-bis(N,N-dimethylthiocarbamate)；2,2'-bis-O-(N,N-dimethylthiocarbamato)-1,1'-binaphthalene；1,1'-binaphthyl-2,2'-diyl O,O-bis(N,N-dimethylthiocarbamate)；2,2'-bis(N,N-dimethylthiocarbamoyloxy)-1,1'-binaphthalene；rac-O,O'-([1,1'-binaphthalene]-2,2'-diyl) bis(dimethylcarbamothioate)；[1,1'-binaphthalene]-2,2'-diyl bis (dimethylcarbamothioate)；binaphthyl-2,2'-diyl O,O-bis(N,N-dimethylthiocarbamate)；2,2'-Bis(N,N-Dimethylthiocarbamoyloxy)-1,1'-binaphtyl；O-[1-[2-(dimethylcarbamothioyloxy)naphthalen-1-yl]naphthalen-2-yl] N,N-dimethylcarbamothioate
• CAS: 189084-88-6
• 化学式: C₂₆H₂₄N₂O₂S₂
• 分子量: 460.621
• InChiKey: FDLOYPFCRZKQAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1,1'-binaphthalene-2,2'-diyl O,O-bis(N,N-dimethylthiocarbamate) 在 nickel/molybdenum on alumina 、 氢气 作用下， 以 萘烷 为溶剂， 300.0~400.0 ℃ 、5.07 MPa 条件下， 反应 7.0h， 生成 1,1'-联萘
  参考文献：
  名称：

  多相加氢脱硫催化剂快速发现和优化的平行比色法

  摘要：

  已经开发了一种基于分光光度法的平行方法来筛选用于加氢脱硫的多相催化剂。该方法利用由 1,1'-联萘噻吩加氢脱硫为 1,1'-联萘产生的光学变化来确定催化剂活性。1,1'-联萘噻吩加氢脱硫为 1,1'-联萘导致联萘环系统中的共轭损失。这导致紫外-可见光谱中超过 60 nm 的蓝移。由于只需要少量的 HDS 催化剂和 1,1'-联萘噻吩，因此可以同时筛选大量催化剂。描述了 1,1'-联萘噻吩的合成和 HDS 催化剂筛选条件。

  DOI：

  10.1021/ja034222j
• 作为产物：
  描述：

  (+)-1,1'-binaphthyl-2,2'-diyl N-<(S)-α-methylbenzyl>thiophosphoroamidate 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (R)-(+)-1,1'-binaphthalene-2,2'-diyl O,O-bis(N,N-dimethylthiocarbamate)
  参考文献：
  名称：

  Preparation of enantiomerically pure 1,1'-binaphthalene-2,2'-diol and 1,1'-binaphthalene-2,2'-dithiol

  摘要：

  A practical preparation of enantiomerically pure 1,1'-binaphthalene-2,2'-diol (1) and 1,1'-binaphthalene-2,2'-dithiol (2) is reported. Enantiopure 2 is obtained from enantiopure 1 via Newman-Kwart rearrangement of the thiocarbamoyl derivative 5 under controlled reaction conditions. The enantiopure starting diol 1 was obtained by a simple and inexpensive method engaging condensation of thiophosphoryl chloride and (S)-(-)-alpha-methylbenzylamine in pyridine and reaction of the resulting phosphoramidate a with racemic binaphthol 1 to give quantitatively a 1:1 mixture of diastereoisomers 4 that were cleanly separated by a single recrystallization from a chloroform-ethanol mixture in very high yield. The procedures can be scaled up easily.

  DOI：

  10.1021/jo00059a025

文献信息

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  DOI：10.1002/anie.202102518

  日期：2021.6.7

  A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric

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  作者：Yong-Hwan Cho、Asato Kina、Toyoshi Shimada、Tamio Hayashi

  DOI：10.1021/jo035880p

  日期：2004.5.1

  2-mercapto-2‘-substituted-1,1‘-biphenyls (8a−c) and 2-mercapto-2‘-substituted-1,1‘-binaphthyls (8d) in high yields. The mercapto group in the axially chiral cross-coupling products was converted into several functional groups by way of the methylsulfinyl group. The rate of flipping in dinaphthothiophene was measured by variable-temperature 31P NMR analysis of methylphenylphosphinyldinaphthothiophene derivative (21)

  1,9-二取代的二苯并噻吩（6a - c）和二萘并噻吩（6d）与芳基和烷基格利雅试剂（7）的催化不对称格利雅交叉反应在存在a的情况下以高对映选择性（高达ee的95％）进行在THF中与2-二苯基膦-1,1'-联萘基（H-MOP）或恶唑啉-膦配体（i -Pr-phox）配位的镍催化剂（3-6 mol％）得到2-巯基-2'-取代的-1,1'-联苯（8a - c）和2-巯基-2'-取代的1,1'-联萘基（8d）高产。轴向手性交叉偶联产物中的巯基通过甲基亚磺酰基基团转化为几个官能团。通过对甲基苯基膦基二萘并噻吩衍生物（21）的可变温度31 P NMR分析来测量二萘并噻吩的翻转速率。
• Pyridinium 1,1′-Binaphthyl-2,2′-disulfonates as Highly Effective Chiral Brønsted Acid−Base Combined Salt Catalysts for Enantioselective Mannich-Type Reaction
  作者：Manabu Hatano、Toshikatsu Maki、Katsuhiko Moriyama、Manabu Arinobe、Kazuaki Ishihara

  DOI：10.1021/ja806875c

  日期：2008.12.17

  established, for the first time, a practical synthesis of chiral 1,1'-binaphthyl-2,2'-disulfonic acid (BINSA 1) from inexpensive BINOL. An efficient enantioselective catalysis in the Mannich-type reactions of diketones and ketoester equivalents with aldimines was developed using chiral 1-achiral 2,6-diarylpyridine (2) combined salts, which acted as convenient chiral tailor-made Brønsted acid-base organocatalysts

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• Highly Practical BINOL-Derived Acid-Base Combined Salt Catalysts for the Asymmetric Direct Mannich-Type Reaction
  作者：Kazuaki Ishihara、Manabu Hatano

  DOI：10.1055/s-0030-1258296

  日期：2010.11

  salt catalysts for asymmetric reactions, we developed a series of simple, practical, chiral BINOL-derived salt catalysts, such as chiral pyridinium 1,1′-binaphthyl-2,2′-disulfonates 1, chiral lithium(I) binaphtholate 2, chiral magnesium(II) binaphtholate (3), chiral calcium(II) phosphate 4, and chiral phosphoric acid 5, which were particularly effective for direct Mannich-type reactions. 1 Introduction

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• Photocatalyzed <i>E</i> → <i>Z</i> Contra‐thermodynamic Isomerization of Vinyl Boronates with Binaphthol
  作者：Thibaud Brégent、Jean‐Philippe Bouillon、Thomas Poisson

  DOI：10.1002/chem.202102536

  日期：2021.10.7

  The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was

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