N-萘酰2-氨基-3-丁烯-1-醇 | 174810-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: N-萘酰2-氨基-3-丁烯-1-醇
• 中文别名: (R)-N-萘酰2-氨基-3-丁烯-1-醇
• 英文名称: (+)-2-[(1R)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione
• 英文别名: (R)-2-(1-hydroxybut-3-en-2-yl)isoindoline-1,3-dione；(R)-N-(1-hydroxymethyl-2-propenyl)phthalimide；(R)-2-(isoindolin-2-yl)but-3-en-1-ol；(R)-N-phthalimidovinylglycinol；(R)-phthalimidovinylglycinol；2-N-phthalimido-3-buten-1-ol；2-[(2R)-1-hydroxybut-3-en-2-yl]isoindole-1,3-dione
• CAS: 174810-06-1
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: XWARCKJYBAUGMZ-MRVPVSSYSA-N

物化性质

• 熔点：
  62.2 °C
• 沸点：
  382.2±35.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  29251995
• 安全说明：
  S26,S37/39
• 储存条件：
  存储于阴凉干燥处。

SDS

Name:	(R)-N-Phthaloyl-2-Aminobut-3-en-1-ol 95% (98% E.E.) Material Safety Data Sheet
Synonym:	None Known
CAS:	174810-06-1

Section 1 - Chemical Product MSDS Name:(R)-N-Phthaloyl-2-Aminobut-3-en-1-ol 95% (98% E.E.) Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
174810-06-1	(R)-N-Phthaloyl-2-Aminobut-3-en-1-ol	95%	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. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. Do NOT use mouth-to-mouth resuscitation.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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# 174810-06-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 62.2 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:
Specific Gravity/Density:
Molecular Formula: C12H11NO3
Molecular Weight: 217.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 174810-06-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-N-Phthaloyl-2-Aminobut-3-en-1-ol - 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# 174810-06-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 174810-06-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 174810-06-1 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：

  N-萘酰2-氨基-3-丁烯-1-醇 在 (acetylacetonato)dicarbonylrhodium (l) 、 C₆₀H₈₈O₇P₂Si₄ 、 氢气 、 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 80.0 ℃ 、1.0 MPa 条件下， 反应 17.0h， 生成 C₂₀H₂₂N₂O₃
  参考文献：
  名称：

  A highly regioselective hydroformylation of an α-chiral olefin to produce a versatile trifunctionalised orthogonally protected C5 synthon

  摘要：

  This paper describes a highly regioselective hydroformylation of (R)-N-phthalimido-vinylglycinol, [(R)-PVG]. By judicious choice of the reaction conditions, catalyst-controlled preferential formation of the linear regioisomer could be achieved in excellent yield. The hydroformylation product cyclised to a hemi-acetal, which is an orthogonally protected trifunctionalised enantio-enriched C5 synthon. The value of this versatile intermediate was demonstrated by the ready formation of enantio-enriched amino-diols, diamino-alcohols and differentially protected (R)-3-aminopiperidine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.062
• 作为产物：
  描述：

  环氧丁烯 、 邻苯二甲酸亚胺 在 bis(η3-allyl-μ-chloropalladium(II)) 、 N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide] 、 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 14.17h， 以99%的产率得到N-萘酰2-氨基-3-丁烯-1-醇
  参考文献：
  名称：

  （+）-丝氨酰胺A † ‡的对映选择性全合成

  摘要：

  描述了一种由外消旋的丁二烯单环氧化物作为起始原料制备（+）-丝氨酰胺A 1的短而高效的对映选择性合成方法。该合成利用钯催化的Trost的动态动力学不对称转化（DYKAT）和交叉复分解（CM）作为关键步骤。

  DOI：

  10.1039/c5ra06609c

文献信息

• 手性β-取代-α,β-不饱和氨基醇类化合物的制 备方法
  申请人：上海交通大学

  公开号：CN104447495B

  公开（公告）日：2017-08-01

  本发明公开了一种手性β‑取代‑α，β‑不饱和氨基醇类化合物的制备方法；在氮气气氛下，在溶剂和钯的手性催化剂存在的条件下，β‑取代‑α，β‑不饱和碳酸酯类化合物(I)发生不对称烯丙基取代反应，生成手性β‑取代‑α，β‑不饱和氨基醇类化合物(II)。本发明的制备方法条件温和、操作简便且能实现良好的反应收率以及对映选择性，具有较好的应用前景。
• Enantioselective Iridium-Catalyzed Allylic Aminations of Allylic Carbonates with Functionalized Side Chains. Asymmetric Total Synthesis of (<i>S</i>)-Vigabatrin
  作者：Günter Helmchen、Christian Gnamm、Géraldine Franck、Nicole Miller、Timon Stork、Kerstin Brödner

  DOI：10.1055/s-0028-1083158

  日期：——

  Iridium-catalyzed aminations of allylic carbonates containing a variety of O-functional groups have been explored. High degrees of regio- as well as enantioselectivity were achieved with diacylamides under salt-free conditions and with arylamines. The results allowed the antiepilepsy drug (S)-vigabatrin to be prepared via a very short route.

  已经探索了含有多种O-官能团的烯丙基碳酸酯的铱催化胺化。在无盐条件下使用二酰胺和芳胺可实现高度的区域选择性和对映选择性。结果使抗癫痫药（S）-氨己烯酸可以通过非常短的路线制备。
• Discovery of 4,7-Diamino-5-(4-phenoxyphenyl)-6-methylene-pyrimido[5,4-<i>b</i>]pyrrolizines as Novel Bruton’s Tyrosine Kinase Inhibitors
  作者：Yu Xue、Peiran Song、Zilan Song、Aoli Wang、Linjiang Tong、Meiyu Geng、Jian Ding、Qingsong Liu、Liping Sun、Hua Xie、Ao Zhang

  DOI：10.1021/acs.jmedchem.8b00441

  日期：2018.5.24

  An alternative medicinal chemistry approach was conducted on Bruton’s tyrosine kinase (BTK) inhibitor 1 (ibrutinib) by merging the pyrazolo[3,4-d]pyrimidine component into a tricyclic skeleton. Two types of compounds were prepared, and their biochemical activities on BTK as well as stereochemistry effects were determined. Structural optimization focusing on the reactive binding group to BTK Cys481

  通过将吡唑并[3,4- d ]嘧啶组分合并成三环骨架，对布鲁顿酪氨酸激酶（BTK）抑制剂1（依鲁替尼）进行了另一种药物化学处理。制备了两种类型的化合物，并确定了它们对BTK的生化活性以及立体化学作用。进行了结构优化，重点是与BTK Cys481的反应性结合基团和以代谢研究为指导的代谢位点。7S被认为是最有效的，对BTK的IC 50值为0.4 nM，对BTK依赖的TMD8细胞的IC 50为16 nM。相比1，7S对B细胞受体信号通路的抑制作用强一些。在源自TMD8细胞的动物异种移植模型中，7S在15 mg / kg QD剂量下显示出5.3的相对肿瘤体积，在25 mg / kg QD较高剂量下比1（RTV 6.6）更有效。所有这些结果表明7S是一种值得进一步分析的新型BTK抑制剂。
• Enantioselective Synthesis of Jaspine B (Pachastrissamine) and Its C-2 and/or C-3 Epimers
  作者：Josep Llaveria、Yolanda Díaz、M. Isabel Matheu、Sergio Castillón

  DOI：10.1002/ejoc.201001477

  日期：2011.3

  Jaspine B and its C-2 and/or C3 epimers have been enantio-selectively prepared from butadiene monoepoxide through a synthetic procedure consisting of allylic amination by palladium-catalyzed dynamic kinetic asymmetric transformation, cross metathesis, and stereoselective dihydroxylation as key steps.

  Jaspine B 及其 C-2 和/或 C3 差向异构体已经从丁二烯单环氧化物通过合成程序对映选择性制备，该合成程序包括通过钯催化的动态动力学不对称转化、交叉复分解和立体选择性二羟基化的烯丙基胺化作为关键步骤。
• [EN] EFFICIENT METHODS FOR Z- OR CIS-SELECTIVE CROSS-METATHESIS<br/>[FR] PROCÉDÉS EFFICACES DE MÉTATHÈSE CROISÉE Z-SÉLECTIVE OU CIS-SÉLECTIVE
  申请人：TRUSTEES BOSTON COLLEGE

  公开号：WO2011097642A1

  公开（公告）日：2011-08-11

  The present invention generally relates to methods for performing metathesis reactions, including cross-metathesis reactions. Methods described herein exhibit enhanced activity and stereoselectivity, relative to known methods, and are useful in the synthesis of a large assortment of biologically and therapeutically significant agents.

  本发明通常涉及进行重要反应的方法，包括交叉重要反应。本文描述的方法相对于已知方法表现出增强的活性和立体选择性，并且在合成大量生物学和治疗上重要的药物方面非常有用。