ethyl (1SR,2RS,3SR,4RS)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate hydrochloride | 95630-74-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (1SR,2RS,3SR,4RS)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate hydrochloride
• 英文别名: ethyl 2-endo-aminobicyclo<2.2.1>hept-5-ene-1-endo-carboxylate hydrochloride；ethyl diendo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate hydrochloride；ethyl endo-3-aminobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate hydrochloride；ethyl endo-3-aminobicyclo<2.2.1>hept-5-ene-endo-2-carboxylate hydrochloride；(rac-di-endo)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester hydrochloride；Ethyl endo-aminobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate；ethyl (1R,2S,3R,4S)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate;hydrochloride
• CAS: 95630-74-3
• 化学式: C₁₀H₁₅NO₂*ClH
• 分子量: 217.696
• InChiKey: PBLUKJJZYDTALO-NPPHLGRCSA-N

物化性质

• 熔点：
  191-192 °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)：
  1.12
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  53.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 储存条件：
  存放在阴凉干燥处即可。

SDS

Name:	Ethyl 3-Endo-Aminobicyclo[2.2.1]Hept-5-ene -2-Endo-Carboxylate Material Safety Data Sheet
Synonym:	None
CAS:	95630-74-3

Section 1 - Chemical Product MSDS Name:Ethyl 3-Endo-Aminobicyclo[2.2.1]Hept-5-ene -2-Endo-Carboxylate Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
95630-74-3	Ethyl 3-endo-aminobicyclo (2,2,1) hept	98	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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 immediately.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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:

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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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 95630-74-3: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 191 - 192 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water: soluble
Specific Gravity/Density:
Molecular Formula: C10H15NO2.HCl
Molecular Weight: 217.69

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 95630-74-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 3-endo-aminobicyclo (2,2,1) hept-5-e ne-2-endo-carbox - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 95630-74-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 95630-74-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 95630-74-3 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：

  ethyl (1SR,2RS,3SR,4RS)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate hydrochloride 在 platinum on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以95%的产率得到ethyl 2-endo-aminobicyclo<2.2.1>heptane-1-endo-carboxylate hydrochloride
  参考文献：
  名称：

  Stajer, Geza; Szabo, Angela E.; Fueloep, Ferenc, Chemische Berichte, 1987, vol. 120, p. 259 - 264

  摘要：

  DOI：
• 作为产物：
  描述：

  乙醇 、 di-endo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid 在 氯化亚砜 作用下， 反应 3.0h， 以75%的产率得到ethyl (1SR,2RS,3SR,4RS)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate hydrochloride
  参考文献：
  名称：

  具有多个立体中心的新型氮杂杂环β-氨基酯立体异构体的立体控制合成

  摘要：

  通过涉及 N-烯丙基化/炔丙基化、开环复分解和化学分化选择性闭环的立体控制合成方案，从容易获得的不饱和双环 β-氨基酸中实现了一些具有多个立体中心的新型功能化氮杂杂环 β-氨基酯的合成。闭环复分解（RCM）。在各种实验条件下研究了RCM转化，分析了催化剂的范围、产率、转化率和底物效应。起始（氧杂）降冰片烯 β-氨基酸的结构预先确定了新的氮杂杂环衍生物的结构；合成过程继续保持立体中心的构型。

  DOI：

  10.1055/a-1877-3822

文献信息

• Chemoselective, Substrate-directed Fluorination of Functionalized Cyclopentane β-Amino Acids
  作者：Loránd Kiss、Melinda Nonn、Reijo Sillanpää、Matti Haukka、Santos Fustero、Ferenc Fülöp

  DOI：10.1002/asia.201601046

  日期：2016.12.6

  cyclopentane derivatives. The cyclic products incorporating CH2F or CHF2 moieties in their structure have been synthesized from diexo‐ or diendo‐norbornene β‐amino acids following a stereocontrolled strategy. The synthetic study was based on an oxidative transformation of the ring carbon–carbon double bond of the norbornene β‐amino acids, followed by transformation of the resulted „all cis“ and „trans“ diformyl

  这项工作描述了一些高度官能化的环戊烷衍生物的底物定向氟化。遵循立体控制策略，由二氧-或二endo-降冰片烯β-氨基酸合成了结构中包含CH 2 F或CHF 2部分的环状产物。合成研究基于降冰片烯β-氨基酸的环碳-碳双键的氧化转化，然后是通过氟化和“化学增差”转化所得的“所有顺式”和“反式”二甲酰基中间体。
• Synthesis of fluorinated piperidine and azepane β-amino acid derivatives
  作者：Renáta Anita Ábrahámi、Loránd Kiss、Pablo Barrio、Ferenc Fülöp

  DOI：10.1016/j.tet.2016.10.005

  日期：2016.11

  A convenient and robust stereocontrolled procedure has been developed for the synthesis of novel trifluoromethyl-containing piperidine and azepane β-amino ester stereoisomers. The synthesis started from readily available unsaturated bicyclic β-lactams and was based on oxidative cleavage of the ring CC double bond followed by ring closure of the diformyl intermediates in the presence of 2,2,2-trifluoroethylamine

  已经开发了方便且鲁棒的立体控制方法，用于合成新型的含三氟甲基的哌啶和氮杂环庚烷β-氨基酯立体异构体。合成从容易获得的不饱和双环β-内酰胺开始，并且基于环CC双键的氧化裂解，然后在2,2,2-三氟乙胺盐酸盐存在下通过还原胺化对二甲酰基中间体进行闭环。合成方法已有效地扩展到单氟化和二氟化类似物的合成。
• Synthesis of conformationally constrained, orthogonally protected 3-azabicyclo[3.2.1]octane β-amino esters
  作者：Ferenc Fülöp、Brigitta Kazi、Lorand Kiss、Eniko Forro、Istvan Mandity

  DOI：10.3998/ark.5550190.0011.904

  日期：——

  Novel azabicyclic β-amino acid derivatives were readily prepared from diexo or diendo norbornene β-amino acids. The 3-azabicyclo[3.2.1]octane skeleton was obtained by NaIO4mediated cleavage of the dihydroxylated β-amino ester intermediates, followed by reductive amination. Lipase-catalyzed enantioselective ring opening of racemic exo-norbornene β-lactam allowed preparation of the corresponding azabicyclic

  新的氮杂双环 β-氨基酸衍生物很容易从二外或二内降冰片烯 β-氨基酸制备。3-氮杂双环[3.2.1]辛烷骨架是通过NaIO4介导的二羟基化β-氨基酯中间体裂解，然后还原胺化获得的。脂肪酶催化的外消旋外降冰片烯β-内酰胺的对映选择性开环允许以对映体纯形式制备相应的氮杂双环外β-氨基酸。
• Stereochemical studies 87saturated heterdcycles 82
  作者：Ferenc Fülöp、Géza Stájer、Gábor Bernáth、Pál Sohár

  DOI：10.1016/s0040-4020(01)96760-2

  日期：1985.1

  diexo-2-Methylamino and 2-benzylamino-3-hydroxymethylbicyclo [2.2.1]heptanes and the corresponding bicycio [2.2.1] heptenes (5a -d, 7a -d) were synthesized from β-amino acid esters containing the norbornane or norbornene skeleton (3a-d). The aminoalcohols were converted to 5,8- methano -3,1-benzoxazines by reaction with formaldehyde. As established by 1H and 13C NMR spectroscopy, the predominant conformation

  由包含降冰片烷或降冰片烯骨架（3a-d）。通过与甲醛反应将氨基醇转化为5,8-甲醇-3,1-苯并恶嗪。如1 H和13 C NMR光谱所确定的，主要构象是二叉基的内-船形（B），二叉基衍生物的是外-船形（E）。
• Preparation of uracil by cycloreversion. Structure of cycloalkane/ene- and norbornane/ene-fused dihydrouracils
  作者：Samuel Frimpong-Manso、Katalin Nagy、Géza Stájer、Gábor Bernáth、Pál Sohár

  DOI：10.1002/jhet.5570290140

  日期：1992.1

  formed from trans-4-cyclohexene-1-carboxylate, furnished the cis-fused 5,6-dihydropyrimidine-2,4(1H,3H)-dione. On heating, the norbornene-diexo-fused dihydrouracil 16 yielded 2,4-pyrimidinedione through the splitting-off of cyclopentadiene. The structures of the compounds were proved by 1H and 13C nmr spectroscopy.

  2-氨基-1-环烷烃，环烯烃，降冰片烷和降冰片烯羧酸酯1–9与氰酸钾的反应生成脲酯，然后将其酯化成环烷烃，环烯，降冰片烷和降冰片烯稠合的5,6-。二氢尿嘧啶10-17。在环化中，由反式-4-环己烯-1-羧酸酯形成的脲酯提供了顺式稠合的5,6-二氢嘧啶-2,4（1 H，3 H）-二酮。加热时，降冰片烯-二烯基稠合的二氢尿嘧啶16通过环戊二烯的分解产生2，4-嘧啶二酮。化合物的结构由1 H和13证明C nmr光谱。