3,3'-二(9-菲基)-1,1'-联萘-2,2'-二醇 | 957111-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 3,3'-二(9-菲基)-1,1'-联萘-2,2'-二醇
• 中文别名: (S)-3,3-二-9-菲基-1,1-联萘酚
• 英文名称: (R)-dianthracenylbinol
• 英文别名: (R)-3,3'-bis(9-phenanthryl)-1,1'-binaphthalene-2,2'-diol；(R)-3,3′-di-9-phenanthrenyl-1,1′-bi-2-naphthol；(R)-3,3'-di(phenanthren-9-yl)-1,1'-binaphthalene-2,2'-diol；(R)-3,3'-bis(9-phenanthryl)-2,2'-dihydroxy-1,1'-binaphthyl；(1S)-3,3'-Di(phenanthren-9-yl)-1,1'-binaphthyl-2,2'-diol；1-(2-hydroxy-3-phenanthren-9-ylnaphthalen-1-yl)-3-phenanthren-9-ylnaphthalen-2-ol
• CAS: 957111-25-0
• 化学式: C₄₈H₃₀O₂
• 分子量: 638.765
• InChiKey: XYUOTCUHTHQCNC-UHFFFAOYSA-N

物化性质

• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  50
• 可旋转键数：
  3
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (1S)-3,3’-Di(phenanthren-9-yl)-1,1’-binaphthyl-2,2’-diol
Synonyms: (1S)-3,3’-Di(phenanthren-9-yl)-1,1’-binaphthalene-2,2’-diol

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: (1S)-3,3’-Di(phenanthren-9-yl)-1,1’-binaphthyl-2,2’-diol
CAS number: 957111-25-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C48H30O2
Molecular weight: 638.8

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,3'-二(9-菲基)-1,1'-联萘-2,2'-二醇 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以95%的产率得到C₄₈H₂₈ClO₃P
  参考文献：
  名称：

  手性N-Triflyl磷酰胺和TiCl4催化未活化烯烃的不对称分子内氢烷氧基化反应

  摘要：

  通过使用手性N- triflyl磷酰胺和TiCl 4的组合，开发了一种新的未活化烯烃不对称分子内氢烷氧基化的新工艺，以51％-99％的收率和30％-71％ee的产率生产了各种手性四氢呋喃衍生物。 。

  DOI：

  10.1002/cjoc.201900544
• 作为产物：
  描述：

  (R)-(+)-2,2’-双(甲氧基甲氧基)-1,1’-联萘 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 苯 为溶剂， 反应 70.12h， 生成 3,3'-二(9-菲基)-1,1'-联萘-2,2'-二醇
  参考文献：
  名称：

  Chiral BINOL-based borate counterions: from cautionary tale on anion stability to enantioselective Cu-catalyzed cyclopropanation

  摘要：

  对一种新型手性BINOL基硼对离子的研究表明，它能够在反应条件下重排，生成可用于铜催化的烯烃环丙基化反应的配体。

  DOI：

  10.1039/d2cc05924j

文献信息

• Synthesis and application of bulky phosphoramidites: highly effective monophosphorus ligands for asymmetric hydrosilylation of styrenes
  作者：Feng Zhang、Qing-Hua Fan

  DOI：10.1039/b909334f

  日期：——

  A series of bulky monodentate phosphoramidite ligands were synthesized from chiral 3,3′-diaryl substituted BINOL derivatives and achiral or dendritic amines in good yields. Asymmetric hydrosilylation of styrenes with trichlorosilane in the presence of palladium complexes of these bulky ligands gave chiral silanes in high yields with excellent activity and productivity. Oxidation of these chiral silanes

  从手性3,3'-二芳基取代的BINOL衍生物和非手性或树枝状胺合成了一系列庞大的单齿亚磷酰胺配体，收率很高。苯乙烯与硅的不对称氢化硅烷化三氯硅烷在这些庞大的配体的钯配合物存在下，以高产率得到具有优异活性和生产率的手性硅烷。这些手性硅烷的氧化过氧化氢 得到了最高96％ee的相应手性仲醇。
• <i>Pyro</i>-Borates, <i>Spiro</i>-Borates, and Boroxinates of BINOL—Assembly, Structures, and Reactivity
  作者：Gang Hu、Anil K. Gupta、Li Huang、Wenjun Zhao、Xiaopeng Yin、Wynter E. G. Osminski、Rui H. Huang、William D. Wulff、Joseph A. Izzo、Mathew J. Vetticatt

  DOI：10.1021/jacs.7b02317

  日期：2017.8.2

  VANOL or VAPOL. Borate esters of BINOL have been investigated as chiral catalysts, and these include meso-borates, spiro-borates, and diborabicyclo-borate esters. Borate esters are often in equilibrium, and their structures can be determined by stoichiometry and/or thermodynamics, especially in the presence of a base. The present study examines the structures of borate esters of BINOL that are produced

  已知 VANOL 和 VAPOL 配体与三当量的 B(OPh)3 反应形成一种催化物质，该物质包含具有三个硼原子的硼酸核，这些已被证明是许多反应的有效催化剂。然而，不知道密切相关的 BINOL 配体是否同样会形成硼酸物质。简单地观察到，与具有 VANOL 或 VAPOL 的相同混合物相比，BINOL 和 B(OPh)3 的混合物是非常差的催化剂。BINOL 的硼酸酯已被研究作为手性催化剂，其中包括内消旋硼酸酯、螺硼酸酯和二硼双环硼酸酯。硼酸酯通常处于平衡状态，它们的结构可以通过化学计量和/或热力学来确定，尤其是在碱的存在下。本研究检查了 BINOL 的硼酸酯的结构，这些 BINOL 的硼酸酯在碱存在和不存在的情况下由 BINOL 与 B(OPh)3 的不同化学计量组合产生。根据条件，可以生成焦硼酸盐、螺硼酸盐和硼酸盐物质，并评估它们在催化不对称氮丙啶化反应中的有效性。发现是 BINOL 硼酸盐物质不一定比
• [EN] NOVEL PROCESSES FOR MAKING SUBSTITUTED QUINAZOLINE COMPOUNDS USING HYDROGEN BONDING CATALYSTS<br/>[FR] NOUVEAUX PROCÉDÉS DE PRODUCTION DE COMPOSÉS DE QUINAZOLINE SUBSTITUÉS À L'AIDE DE CATALYSEURS DE LIAISON HYDROGÈNE
  申请人：MERCK SHARP & DOHME

  公开号：WO2017091453A1

  公开（公告）日：2017-06-01

  Disclosed herein is a novel process for preparing substituted quinazoline compounds of formula (I) using a hydrogen bonding catalyst.

  本文披露了一种使用氢键催化剂制备式（I）取代喹唑啉化合物的新工艺。
• N-Triflylphosphorimidoyl Trichloride: A Versatile Reagent for the Synthesis of Strong Chiral Brønsted Acids
  作者：Benjamin List、Sunggi Lee、Philip Kaib

  DOI：10.1055/s-0036-1588782

  日期：2017.7

  A series of strong Bronsted acids has been synthesized in high yields using N-triflylphosphorimidoyl trichloride as reagent. The syntheses proceed efficiently with electron-rich, electron-deficient, and sterically hindered substrates.

  使用N-三氟甲酰基磷酰亚胺酰三氯化物作为试剂以高产率合成了一系列强布朗斯台德酸。合成在富电子、缺电子和空间位阻底物下有效进行。
• Photochemical Organocatalytic Functionalization of Pyridines via Pyridinyl Radicals
  作者：Emilien Le Saux、Eleni Georgiou、Igor A. Dmitriev、Will C. Hartley、Paolo Melchiorre

  DOI：10.1021/jacs.2c12466

  日期：2023.1.11

  We report a photochemical method for the functionalization of pyridines with radicals derived from allylic C–H bonds. Overall, two substrates undergo C–H functionalization to form a new C(sp2)–C(sp3) bond. The chemistry harnesses the unique reactivity of pyridinyl radicals, generated upon single-electron reduction of pyridinium ions, which undergo effective coupling with allylic radicals. This novel

  我们报告了一种用源自烯丙基 C-H 键的自由基对吡啶进行功能化的光化学方法。总体而言，两种底物进行 C–H 功能化以形成新的 C(sp 2 )–C(sp 3） 纽带。该化学利用了吡啶基自由基的独特反应性，吡啶基离子在单电子还原时产生，与烯丙基自由基有效偶联。这种新颖的机制使吡啶功能化具有明显的位置选择性，这与经典的 Minisci 化学不同。关键是确定了一种二硫代磷酸，它掌握了三个催化任务，依次充当用于吡啶质子化的布朗斯台德酸、用于吡啶离子还原的单电子转移 (SET) 还原剂和用于激活烯丙基 C(sp 3 )–H键。生成的吡啶基和烯丙基自由基然后以高区域选择性偶联。