ethyl exo-3-aminobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate hydrochloride | 104770-18-5

• 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 exo-3-aminobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate hydrochloride
• 英文别名: ethyl diexo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate hydrochloride；Ethyl exo-aminobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate；ethyl exo-3-aminobicyclo<2.2.1>hept-5-ene-exo-2-carboxylate hydrochloride；3-ethoxycarbonylbicyclo[2.2.1]hept-5-en-2-yl-ammonium chloride；Ethyl 3-exo-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate hydrochloride；ethyl (1S,2S,3R,4R)-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate;hydrochloride
• CAS: 104770-18-5
• 化学式: C₁₀H₁₅NO₂*ClH
• 分子量: 217.696
• InChiKey: PBLUKJJZYDTALO-WZSOELRKSA-N

物化性质

• 熔点：
  129-132 °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)：
  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：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2922499990

SDS

Name:	Ethyl 3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylate Material Safety Data Sheet
Synonym:	None
CAS:	104770-18-5

Section 1 - Chemical Product MSDS Name:Ethyl 3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylate Material Safety Data Sheet
Synonym:None

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
104770-18-5	Ethyl 3-exo-aminobicyclo[2.2.1]hept-5-	99	unlisted

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

---

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.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. 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.

---

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. 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.
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:

---

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 appropriate foam.

---

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

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 104770-18-5: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 130 - 132 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Soluble.
Specific Gravity/Density: Not available.
Molecular Formula: C10H15NO2.HCl
Molecular Weight: 217.69

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
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

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 104770-18-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 3-exo-aminobicyclo[2.2.1]hept-5-ene-2-exo-carboxylate hydrochloride - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 104770-18-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 104770-18-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 104770-18-5 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：

  ethyl exo-3-aminobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate hydrochloride 在 四氧化锇 、 N-甲基吗啉氧化物 、 三乙胺 、 叔丁醇 作用下， 以 四氢呋喃 、 丙酮 、 甲苯 为溶剂， 反应 10.0h， 生成 ethyl (1S*,2R*,3S*,4R*,5R*,6S*)-3-(((benzyloxy)carbonyl)amino)-5,6-dihydroxybicyclo[2.2.1]heptane-2-carboxylate
  参考文献：
  名称：

  官能化的环戊烷β-氨基酸的化学选择性，底物导向的氟化

  摘要：

  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。

  DOI：

  10.1002/asia.201601046
• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 叠氮基三甲基硅烷 、 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 1.0h， 以50%的产率得到ethyl exo-3-aminobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate hydrochloride
  参考文献：
  名称：

  Selective mGAT2 (BGT-1) GABA Uptake Inhibitors: Design, Synthesis, and Pharmacological Characterization

  摘要：

  beta-Amino acids sharing a lipophilic diaromatic side chain were synthesized and characterized pharmacologically on mouse GABA transporter subtypes mGAT1-4. The parent amino acids were also characterized. Compounds 13a, 13b, and 17b displayed more than 6-fold selectivity for mGAT2 over mGAT1. Compound 17b displayed anticonvulsive properties inferring a role of mGAT2 in epileptic disorders. These results provide new neuropharmacological tools and a strategy for designing subtype selective GABA transport inhibitors.

  DOI：

  10.1021/jm301872x

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。
• Stereocontrolled One-Step Synthesis of Difunctionalised Cispentacin Derivatives through Ring-Opening Metathesis of Norbornene β-Amino Acids
  作者：Loránd Kiss、Márton Kardos、Enikő Forró、Ferenc Fülöp

  DOI：10.1002/ejoc.201403493

  日期：2015.2

  Through the ring-opening metathesis of norbornene or oxanorbornene β-amino acids with ethylene in the presence of certain Ru catalysts, a facile and convenient stereocontrolled one-step method was devised for the preparation of divinylated cispentacins and oxacyclic cispentacin stereoisomers with four chiral centres. The products are interesting scaffolds for peptide chemistry and for the synthesis of novel

  通过在某些Ru催化剂存在下降冰片烯或氧杂降冰片烯β-氨基酸与乙烯的开环复分解反应，设计了一种简便的立体控制一步法制备具有四个手性中心的二乙烯基顺喷素和氧杂环戊烯酸立体异构体。这些产品是用于肽化学和通过烯键转换合成新型功能化材料的有趣支架。开环复分解不影响起始分子的手性中心，因此它们的立体化学是保守的，并决定了产物中手性中心的构型。
• 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。