(R)-(-)-1-(Alpha-氨基苄基)-2-萘酚 | 219897-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (R)-(-)-1-(Alpha-氨基苄基)-2-萘酚
• 中文别名: (R)-(-)-1-(氨基苯甲酰基)-2-奈酚；(R)-(-)-1-(ALPHA-氨基苄基)-2-萘酚；R)-(-)-1-(ALPHA-氨基苄基)-2-萘酚；(R)-(-)-1-(α-氨基苄基)-2-萘酚
• 英文名称: (R)-1-[amino(phenyl)methyl]naphthalen-2-ol
• 英文别名: (R)-1-(α-aminobenzyl)-2-naphthol；R(-)-1-(α-aminobenzyl)-2-napthol；(R)-Betti base；R(-)-Betti base；(R)-(-)-1-(alpha-Aminobenzyl)-2-naphthol；1-[(R)-amino(phenyl)methyl]naphthalen-2-ol
• CAS: 219897-35-5
• 化学式: C₁₇H₁₅NO
• mdl: MFCD04972352
• 分子量: 249.312
• InChiKey: PZMIGEOOGFFCNT-QGZVFWFLSA-N

物化性质

• 熔点：
  131-132 °C
• 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)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.058
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2922299090
• 安全说明：
  S26,S37/39
• 储存条件：
  存放于4℃阴凉干燥处

SDS

Name:	(R)-(-)-1-(alpha-Aminobenzyl)-2-naphthol 99% Material Safety Data Sheet
Synonym:	(R)-Betti bas
CAS:	219897-35-5

Section 1 - Chemical Product MSDS Name:(R)-(-)-1-(alpha-Aminobenzyl)-2-naphthol 99% Material Safety Data Sheet
Synonym:(R)-Betti bas

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
219897-35-5	(R)-(-)-1-(alpha-Aminobenzyl)-2-naphth	99%	unlisted

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

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.Moisture sensitive.
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.

---

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.

---

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.

---

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.

---

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Keep refrigerated. (Store below 4C/39F.) Store in a tightly closed container. Store in a dry area.

---

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# 219897-35-5: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 131 - 132 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: 259 deg C
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C17H15NO
Molecular Weight: 249.31

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong reducing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 219897-35-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(R)-(-)-1-(alpha-Aminobenzyl)-2-naphthol - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

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

---

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.

---

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 36 Wear suitable protective clothing.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 219897-35-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 219897-35-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 219897-35-5 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (R)-(-)-1-(Alpha-氨基苄基)-2-萘酚 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  手性（硫代）磷二酰胺是出色的氢键供体催化剂，用于将2-羟基-1,4-萘醌酮不对称迈克尔加成到硝基烯烃中。

  摘要：

  已经开发出了一种新型的基于（硫代）磷二酰胺基阴极的双齿氢键供体催化剂，用于将2-羟基-1,4-萘并醌不对称地迈克尔加成到硝基烯烃中，从而以高收率提供相应的加合物，同时具有出色的对映选择性（ 97-> 99％ee）。

  DOI：

  10.1039/c1cc10797f
• 作为产物：
  描述：

  (R)-3,3-dimethyl-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine 在 D-酒石酸 、 sodium carbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 (R)-(-)-1-(Alpha-氨基苄基)-2-萘酚
  参考文献：
  名称：

  柔性自折叠空腔中的对映选择性分子识别

  摘要：

  我们报告了一种基于杯 [5] 芳烃的手性深腔受体，该受体通过氢键协同网络稳定并具有高度灵活的结构。cavitand 显示出对一系列手性季铵盐的对映选择性分子识别，在相应的非对映体主客体复合物之间提供前所未有的稳定性比。分子动力学模拟证实了新宿主的更高灵活性以及与间苯二酚 [4] 芳烃衍生的自折叠腔体有关的优异诱导拟合行为的出现。

  DOI：

  10.1021/acs.orglett.3c00463
• 作为试剂：
  描述：

  tert-butyl 4-methylbenzoperoxoate 、 环己烯 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 (R)-(-)-1-(Alpha-氨基苄基)-2-萘酚 作用下， 以 乙腈 为溶剂， 以46%的产率得到
  参考文献：
  名称：

  手性 Betti 碱-铜络合物在烯烃对映选择性烯丙基氧化中的应用、Betti 碱的计算研究以及所得手性烯丙基酯的对接

  摘要：

  手性( R )-和( S )-Betti碱通过非对映异构重结晶法使用l -(+)-酒石酸拆分相应的外消旋混合物初步合成，然后研究了Betti碱的铜配合物烯烃的对映选择性烯丙基 C H 键氧化。这种配体在优化条件下产生了具有良好到高产率和令人满意的对映选择性的对映体富集的烯丙基酯。此外，使用M06–2X方法和6–311 ++ G ( d ,p）基组。此外，已使用 AutoDock Vina 研究了合成的手性烯丙基酯对 PI3Kα 酶的生物活性。

  DOI：

  10.1016/j.mcat.2023.113011

文献信息

• A Chiral Amino-Naphthalene-Derived Prolinamide Catalyst for the Enantioselective Michael Addition of Ketones to Nitroolefins
  作者：Chuanming Yu、Ke Zhang、Xiangjun Shi

  DOI：10.3184/174751912x13332916163195

  日期：2012.5

  An enantioselective Michael addition of ketones to nitroolefins has been accomplished using a novel chiral amino-naphthalene-derived prolinamides catalyst 1. The desired Michael adducts were obtained in high yields (up to 93%) as well as good diastereoselectivities (>99:1) and enantioselectivities (48%-99% ee).

  使用新型手性氨基萘衍生的脯氨酰胺催化剂 1 实现了酮与硝基烯烃的对映选择性迈克尔加成。 以高产率（高达 93%）和良好的非对映选择性（>99:1）获得了所需的迈克尔加合物和对映选择性 (48%-99% ee)。
• Processes for the Preparation of Tasimelteon and Intermediates Thereof
  申请人：Apotex Inc.

  公开号：US20170355688A1

  公开（公告）日：2017-12-14

  The present invention provides processes for the preparation of Tasimelteon (1), as well as processes for the preparation of intermediates of Formulas (2), (3) and (4) useful in the preparation of Tasimelteon (1).

  本发明提供了制备Tasimelteon（1）的工艺，以及制备用于制备Tasimelteon（1）的中间体Formula（2）、（3）和（4）的工艺。
• Asymmetric Aza-Friedel-Crafts Reaction of 2-Naphthol with Tosylimines Catalyzed by a Dinuclear Zinc Complex
  作者：Xin-Ping Hui、Liang-Feng Niu、Yang-Chun Xin、Ren-Lin Wang、Fan Jiang、Peng-Fei Xu

  DOI：10.1055/s-0029-1219390

  日期：2010.3

  The first asymmetric aza-Friedel-Crafts reaction of 2-naphthol with tosylimines was developed via a dinuclear zinc catalyst (up to 98% ee). It provided a new method for the asymmetric synthesis of Betti base derivatives.

  首个通过二核锌催化剂实现的2-萘醇与托西亚胺的不对称亚弗里德尔-克拉夫茨反应被开发出来（最高可达98%外消旋度）。该方法为Betti碱衍生物的不对称合成提供了一种新途径。
• A New Method for the Synthesis of Enantiomerically Pure Betti Base
  作者：Ling Song、Guangling Bian、Shiwei Yang、Huayin Huang

  DOI：10.1055/s-0032-1318272

  日期：——

  using recyclable (R)-1,1′-binaphthalene-2,2′-diyl sodium phosphate to provide enantiomerically pure (S)-Betti base in 95% yield with up to 99% ee and (R)-Betti base in 93% yield with 90% ee in one resolution step. We have developed a new method for the synthesis of enantiomerically pure Betti base. By using trifluoroacetic acid to replace the more traditionally used hydrochloride acid, the hydrolysis

  摘要 我们已经开发了一种合成对映体纯的Betti碱的新方法。通过使用三氟乙酸代替更常用的盐酸盐，在温和的条件下进行了经典的外消旋贝蒂碱合成中使用的水解步骤，提高了收率（高达96％），随后是一种新的高效方法。使用可回收的（R）-1,1'-联萘-2,2'-二烷基磷酸钠进行拆分以提供对映体纯的（S）-Betti碱，收率95％，ee和（R）-Betti碱最高达99％一步分离得到93％的收率和90％的ee。 我们已经开发了一种合成对映体纯的Betti碱的新方法。通过使用三氟乙酸代替更常用的盐酸盐，在温和的条件下进行了经典的外消旋贝蒂碱合成中使用的水解步骤，提高了收率（高达96％），随后是一种新的高效方法。使用可回收的（R）-1,1'-联萘-2,2'-二烷基磷酸钠进行拆分以提供对映体纯的（S）-Betti碱，收率95％，ee和（R）-Betti碱最高达99％一步分离得到93％的收率和90％的ee。
• Enantioselective Synthesis of Highly Functionalized Trifluoromethyl-Bearing Cyclopentenes: Asymmetric [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Trifluoroethylidenemalonates Catalyzed by Multifunctional Thiourea-Phosphines
  作者：Hong-Ping Deng、Yin Wei、Min Shi

  DOI：10.1002/adsc.201101012

  日期：2012.3.16

  synthesis of multifunctional thiourea‐phosphines, a catalytic method for the asymmetric [3+2] annulation of Morita–Baylis–Hillman carbonates with trifluoroethylidenemalonates has been developed, affording highly functionalized trifluoromethyl‐bearing cyclopentenes in excellent yields, high diastereoselectivities and enantioselectivities under mild conditions.

  在设计和合成多功能硫脲膦的基础上，开发了一种催化方法，用于森田-贝利斯-希尔曼碳酸盐与三氟亚乙基丙二酸酯的不对称[3 + 2]环合，提供了具有高收率的高度官能化的含三氟甲基的环戊烯，在温和条件下具有较高的非对映选择性和对映选择性。