2,6-二[(4S)-4-苯基-2-恶唑啉基]吡啶 | 174500-20-0

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2,6-二[(4S)-4-苯基-2-恶唑啉基]吡啶
• 中文别名: (S,S)-2,6-双(4-苯基-2-恶唑啉-2-基)吡啶；(S,S)-2,2'-(2,6-吡啶二基)双(4-苯基-2-恶唑啉；2,6-二[(4S)-4-苯基-2-噁唑啉基]吡啶；2,6-二[(4S)-4-苯基-2-恶唑啉基；2,6-双[(4S)-4-苯基-2-恶唑啉]吡啶；2,6-双[(4S)-4-苯基-2-噁唑啉基]吡啶；(S,S)-2,6-双(4,5-二氢-4-苯基-2-噁唑基)吡啶；(S,S)-2,6-双(4-苯基-2-噁唑啉基)吡啶；(-)-2,6-双((4S)-4-苯基-2-恶唑啉)吡啶；2,6-二((4S)-4-苯基-2-恶唑啉基)吡啶
• 英文名称: (S,S)-2,6-bis(4-phenyl-2-oxazolinyl)pyridine
• 英文别名: 2,6-bis[(4S)-4-phenyl-2-oxazolinyl]pyridine；(S,S)-Ph-PyBox；(S,S)-2,6-bis(4-phenyl-2-oxazolin-2-yl)pyridine；(4S)-4-phenyl-2-[6-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl]-4,5-dihydro-1,3-oxazole
• CAS: 174500-20-0
• 化学式: C₂₃H₁₉N₃O₂
• 分子量: 369.423
• InChiKey: HLHBIMJNCKZZQO-NHCUHLMSSA-N

物化性质

• 熔点：
  171-175 °C(lit.)
• 比旋光度：
  -224 º (c=1, chloroform)
• 沸点：
  600.4±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  29349990
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Name:	2 6-bis[(4s)-phenyl-2-oxazolin-2-yl]pyridine Material Safety Data Sheet
Synonym:
CAS:	174500-20-0

Section 1 - Chemical Product MSDS Name:2 6-bis[(4s)-phenyl-2-oxazolin-2-yl]pyridine Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
174500-20-0	2,6-bis[(4s)-phenyl-2-oxazolin-2-yl]py		unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Avoid generating dusty conditions.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 174500-20-0: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystals
Color: white
Odor: odorless
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 171 - 175 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C23H19N3O2
Molecular Weight: 369.42

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 174500-20-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,6-bis[(4s)-phenyl-2-oxazolin-2-yl]pyridine - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 174500-20-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 174500-20-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 174500-20-0 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  copper(II) bis(trifluoromethanesulfonate) 、 2,6-二[(4S)-4-苯基-2-恶唑啉基]吡啶 以 二氯甲烷 为溶剂， 生成 copper;(4S)-4-phenyl-2-[6-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl]-4,5-dihydro-1,3-oxazole;trifluoromethanesulfonate
  参考文献：
  名称：

  双（恶唑啉）和双（恶唑啉基）吡啶铜配合物作为对映选择性 Diels-Alder 催化剂：反应范围和合成应用

  摘要：

  已经研究了由双（恶唑啉）铜配合物催化的 Diels-Alder 反应的范围。特别是，[Cu((S,S)-t-Bu-box)](SbF6)2 (1b) 已被证明可以催化 3-propenoyl-2-oxazolidinone (2) 和一系列的 Diels-Alder 反应。具有高对映选择性的取代二烯。这种阳离子复合物也已成功用于类似分子内过程的催化。描述了 ent-Δ1-四氢大麻酚、ent-莽草酸和 isopulo'upone 的全合成，其特点是在更复杂的 Diels-Alder 过程中使用这种手性催化剂。类似地，阳离子铜配合物 9a，[Cu((S,S)-t-Bu-pybox)](SbF6)2，在单齿丙烯醛亲二烯体的 Diels-Alder 反应中是有效的，而密切相关的配合物 9d [Cu ((S,S)-Bn-pybox)](SbF6)2,

  DOI：

  10.1021/ja991191c
• 作为产物：
  描述：

  2,6-吡啶二甲腈 在 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 84.0h， 生成 2,6-二[(4S)-4-苯基-2-恶唑啉基]吡啶
  参考文献：
  名称：

  Kinetic resolution by copper-catalyzed azide–alkyne cycloaddition

  摘要：

  The use of chiral pybox ligands imparts enantioselectivity to the Cu-I-catalyzed azide-alkyne cycloaddition reaction, in the form of kinetic resolution of alpha-chiral azides and desymmetrization of gem-diazides. While levels of selectivity are modest, the results show unequivocally that the process benefits from ligand-accelerated catalysis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.019
• 作为试剂：
  描述：

  4-ethynyl-1-tosyl-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one 、 1,3-bis-(4-methoxy-benzyl)-imidazolidine 在 copper(l) iodide 、 2,6-二[(4S)-4-苯基-2-恶唑啉基]吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 以77 %的产率得到
  参考文献：
  名称：

  一种合成吲哚并1,4-二氮八元杂环类化合物的方法

  摘要：

  本发明属于有机合成领域，公开了一种合成吲哚并1,4‑二氮八元杂环类化合物的方法。具体来说是通过铜催化剂和噁唑啉配体组合，催化4‑乙炔基‑3,1‑苯并噁嗪‑2‑酮类化合物和咪唑类化合物反应制备一系列吲哚并1,4‑二氮八元杂环类化合物的方法。具体操作步骤为：在氩气保护下，向反应管中加入铜催化剂和噁唑啉配体，随后加入4‑乙炔基‑3,1‑苯并噁嗪‑2‑酮类化合物和咪唑烷类化合物，然后升温反应，待反应完全。向反应液中加入DBU，继续升温反应，反应完全后，纯化分离得到吲哚并1,4‑二氮八元杂环化合物。该方法具有底物适用性好，反应条件温和，合成效率高的优点。#imgabs0#

  公开号：

  CN118373826A

文献信息

• Synthetic, spectral and catalytic activity studies of ruthenium bipyridine and terpyridine complexes: Implications in the mechanism of the ruthenium(pyridine-2,6-bisoxazoline)(pyridine-2,6-dicarboxylate)-catalyzed asymmetric epoxidation of olefins utilizing H2O2
  作者：Man Kin Tse、Haijun Jiao、Gopinathan Anilkumar、Bianca Bitterlich、Feyissa Gadissa Gelalcha、Matthias Beller

  DOI：10.1016/j.jorganchem.2005.12.069

  日期：2006.10

  6-[(4S)-4-phenyl-4,5-dihydro-oxazol-2-yl]-[2,2′]bipyridinyl new insights on the reaction intermediates and reaction pathway of the ruthenium-catalyzed enantioselective epoxidation are proposed. In addition, a simplified protocol for epoxidation of olefins using urea hydrogen peroxide complex as oxidizing agent has been developed.

  各种Ru（L 1）（L 2）（1）配合物（L 1  = 2,2'-联吡啶，2,2'：6'，2''-吡啶，6-（4 S）-4-苯基-4 ，5-二氢-恶唑-2-基-2,2'-联吡啶基或2,2'-联吡啶基-6-羧酸酯； L 2  =吡啶-2,6-二羧酸酯，吡啶-2-羧酸吡啶或2,2' -联吡啶基-6-羧酸盐）（已合成（或原位生成）），并使用30％的H 2 O 2水溶液对烯烃进行环氧化测试。含有2，6-二羧酸吡啶的配合物显示出极高的催化活性。基于包含非外消旋2,2'-联吡啶（包括6-[（4 S）-4-苯基-4,5-二氢-恶唑-2-基]-[2,2']联吡啶基对钌催化的对映选择性环氧化反应的中间体和反应途径提出了新的见解。另外，已经开发出使用过氧化氢脲配合物作为氧化剂的烯烃环氧化的简化方案。
• Cobalt-Catalyzed Alkyne Hydrosilylation and Sequential Vinylsilane Hydroboration with Markovnikov Selectivity
  作者：Ziqing Zuo、Ji Yang、Zheng Huang

  DOI：10.1002/anie.201605615

  日期：2016.8.26

  pyridinebis(oxazoline) cobalt complex is a very efficient precatalyst for the hydrosilylation of terminal alkynes with Ph2SiH2, providing α‐vinylsilanes with high (Markovnikov) regioselectivity and broad functional‐group tolerance. The vinylsilane products can be further converted into geminal borosilanes through Markovnikov hydroboration with pinacolborane and a bis(imino)pyridine cobalt catalyst.

  吡啶双（恶唑啉）钴配合物是用于末端炔烃与Ph 2 SiH 2氢化硅烷化的非常有效的预催化剂，可提供具有高（Markovnikov）区域选择性和宽泛的官能团耐受性的α-乙烯基硅烷。乙烯基硅烷产物可以通过与频哪醇硼烷和双（亚氨基）吡啶钴催化剂一起进行的马尔可夫尼科夫硼氢化反应进一步转化为双硼硅硅烷。
• [EN] ANTIFUNGAL COMPOUNDS AND PROCESSES FOR MAKING<br/>[FR] COMPOSÉS ANTIFONGIQUES ET PROCÉDÉS DE PRÉPARATION
  申请人：VIAMET PHARMACEUTICALS INC

  公开号：WO2017049196A1

  公开（公告）日：2017-03-23

  Provided are polymorphic forms of compound 5 or 5*, or mixtures thereof, and polymorph forms of compound 14 or 14*, or mixtures thereof. Also provided are methods of preparing compound 5 or 5*, or mixtures thereof, and methods of preparing compound of 14 or 14*, or mixtures thereof, which are useful as antifungal agents. In particular, provided is new methodology for preparing polymorphs of the compounds described and substituted derivatives thereof.

  提供了化合物5或5*的多态形式，或二者的混合物，以及化合物14或14*的多形式，或二者的混合物。还提供了制备化合物5或5*，或二者的混合物的方法，以及制备化合物14或14*，或二者的混合物的方法，这些方法可用作抗真菌剂。特别提供了制备所述化合物及其取代衍生物的多形式的新方法。
• Copper-Catalyzed Enantioselective Propargylic Etherification of Propargylic Esters with Alcohols
  作者：Kazunari Nakajima、Masashi Shibata、Yoshiaki Nishibayashi

  DOI：10.1021/jacs.5b00004

  日期：2015.2.25

  Enantioselective propargylic etherification of propargylic esters with not only aliphatic alcohols but also phenols in the presence of a catalytic amount of copper-Pybox complex gives the corresponding propargylic ethers in good to high yields with a high to excellent enantioselectivity (up to 99% ee). The result described here provides the first successful example of enantioselective propargylic etherification

  在催化量的铜-Pybox 络合物存在下，炔丙酯与脂肪醇和酚的对映选择性炔丙醚化反应得到相应的炔丙醚，产率良好至高，对映选择性高至极好（高达 99% ee）。这里描述的结果提供了对映选择性炔丙醚化的第一个成功例子。
• Complementing Pyridine‐2,6‐bis(oxazoline) with Cyclometalated N‐Heterocyclic Carbene for Asymmetric Ruthenium Catalysis
  作者：Long Li、Feng Han、Xin Nie、Yubiao Hong、Sergei Ivlev、Eric Meggers

  DOI：10.1002/anie.202004243

  日期：2020.7.20

  6‐bis(oxazoline) (pybox) ligands for asymmetric transition metal catalysis is introduced by adding a bidentate ligand to modulate the electronic properties and asymmetric induction. Specifically, a ruthenium(II) pybox fragment is combined with a cyclometalated N‐heterocyclic carbene (NHC) ligand to generate catalysts for enantioselective transition metal nitrenoid chemistry, including ring contraction

  通过添加双齿配体来调节电子性质和不对称诱导，提出了扩大手性吡啶-2,6-双（恶唑啉）（pybox）配体在不对称过渡金属催化中的应用的策略。具体来说，钌 (II) pybox 片段与环金属化 N-杂环卡宾 (NHC) 配体结合，生成用于对映选择性过渡金属氮烯化学的催化剂，包括环收缩为手性 2H-氮丙啶（2000 TON 时高达 97% ee）和对映选择性 C(sp 3 )−H 胺化（50 TON 时高达 97 % ee）。