di-endo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid | 88330-29-4

• 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: di-endo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• 英文别名: (1R,2S,3R,4S)-3-azaniumylbicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 88330-29-4
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: FCYFJGGJCJDCPB-BNHYGAARSA-N

物化性质

• 熔点：
  265-267 °C
• 沸点：
  276.1°C (rough estimate)
• 密度：
  1.294
• 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)：
  -2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990
• 安全说明：
  S24/25

SDS

Name:	3-Endo-Aminobicyclo2.2.1Hept-5-ene-2- Endo-Carboxylic Acid 98% Material Safety Data Sheet
Synonym:	None known
CAS:	88330-29-4

Section 1 - Chemical Product MSDS Name:3-Endo-Aminobicyclo2.2.1Hept-5-ene-2- Endo-Carboxylic Acid 98% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
88330-29-4	3-Endo-Aminobicyclo2.2.1Hept-5-ene-2	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.
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.

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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. 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:

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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 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:
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:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
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:
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# 88330-29-4: 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: slightly beige
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 265.00 - 267.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble
Specific Gravity/Density:
Molecular Formula: C8H11NO2
Molecular Weight: 153.18

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
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# 88330-29-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Endo-Aminobicyclo2.2.1Hept-5-ene-2- Endo-Carboxylic Acid - 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# 88330-29-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 88330-29-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 88330-29-4 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：

  di-endo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid 在 氢氧化钾 、 lithium aluminium tetrahydride 、 lead(II) nitrate 作用下， 以 四氢呋喃 为溶剂， 反应 20.25h， 生成 5,8-methano-4ar,5t,8t,8ac-tetrahydro-4H-3,1-benzoxazine-2(1H)-thione
  参考文献：
  名称：

  立体化学研究。58。饱和杂环。39 †。与降冰片烷和降冰片烯融合的二氢-1,3-恶嗪，1,3-恶嗪-2-酮和1,3-恶嗪-2-硫酮的制备和空间结构

  摘要：

  3-内氨基双环[2.2.1]庚-5-烯-2-内羧酸（1），由内降冰片烯5-烯-2,3-二羧酸酐和类似的饱和顺式-外氨基酸（3）用氢化铝锂还原成氨基醇2和4 ; 后者通过芳胺基醚环化成亚甲基桥连的四氢-（6a-c）和六氢-3,1-苯并恶嗪（7b-d）。的内（2）和外（4）用氯甲酸乙酯和甲醇钠将氨基醇转化为亚甲基桥连的四氢-3,1-苯并恶嗪-2-酮（9）和六氢-3,1-苯并恶嗪-2-酮（12）；用二硫化碳对醇进行处理，通过二硫代氨基甲酸酯得到相应的2-硫酮（11、13）。结构通过红外光谱和核磁共振谱证实。

  DOI：

  10.1002/jhet.5570200509
• 作为产物：
  描述：

  3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 ammonium hydroxide 、 sodium hydroxide 、 sodium hypochlorite 作用下， 生成 di-endo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid
  参考文献：
  名称：

  立体化学研究。58。饱和杂环。39 †。与降冰片烷和降冰片烯融合的二氢-1,3-恶嗪，1,3-恶嗪-2-酮和1,3-恶嗪-2-硫酮的制备和空间结构

  摘要：

  3-内氨基双环[2.2.1]庚-5-烯-2-内羧酸（1），由内降冰片烯5-烯-2,3-二羧酸酐和类似的饱和顺式-外氨基酸（3）用氢化铝锂还原成氨基醇2和4 ; 后者通过芳胺基醚环化成亚甲基桥连的四氢-（6a-c）和六氢-3,1-苯并恶嗪（7b-d）。的内（2）和外（4）用氯甲酸乙酯和甲醇钠将氨基醇转化为亚甲基桥连的四氢-3,1-苯并恶嗪-2-酮（9）和六氢-3,1-苯并恶嗪-2-酮（12）；用二硫化碳对醇进行处理，通过二硫代氨基甲酸酯得到相应的2-硫酮（11、13）。结构通过红外光谱和核磁共振谱证实。

  DOI：

  10.1002/jhet.5570200509

文献信息

• Synthesis of Novel N-Heterocyclic Compounds Containing 1,2,3-Triazole Ring System via Domino, “Click” and RDA Reactions
  作者：Márta Palkó、Mohamed El Haimer、Zsanett Kormányos、Ferenc Fülöp

  DOI：10.3390/molecules24040772

  日期：——

  synthesized with domino ring closure. A click reaction was performed to create the 1,2,3-triazole heterocyclic ring, followed by an RDA reaction resulting in dihydropyrimido[2,1-a]isoindole-2,6-diones. The absolute configuration, concluded by the norbornene structure that served as a chiral source, remained constant throughout the transformations. The structure of the synthesized compounds was examined by

  已经开发出一种简单、高产的合成路线来构成复杂的杂环，应用多米诺骨牌、点击和逆狄尔斯-阿尔德 (RDA) 反应序列。从 2-氨基甲酰胺开始，合成了一组具有多米诺环闭合的新异吲哚并[2,1-a]喹唑啉酮。进行点击反应以产生 1,2,3-三唑杂环，然后进行 RDA 反应，产生二氢嘧啶并 [2,1-a] 异吲哚-2,6-二酮。由作为手性来源的降冰片烯结构得出的绝对构型在整个转化过程中保持不变。通过 1H 和 13C 核磁共振 (NMR) 方法检查合成化合物的结构。
• Reactions of Levulinic Acid with Norbornane/ene Amino Acids and Diamines
  作者：Géza Stájer、Angela E. Szabó、Antal Csámpai、Pál Sohár

  DOI：10.1002/ejoc.200300604

  日期：2004.3

  Whereas the cyclizations of di-endo-3-aminobicyclo[2.2.1]heptane-2-carboxylic acid (2) and di-endo-3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylic acid (3) with 4-oxopentanoic acid (1) yield methanodioxopyrrolo[1,2-a][3,1]benzoxazines 6 and 7, the di-exo analogues give either the pyrrolo[1,2-a]pyridine 8 as sole product (in the case of 4), or 10 together with the methyl-substituted derivative 9 (in the

  而二-内-3-氨基双环[2.2.1]庚烷-2-羧酸(2)和二-内-3-氨基双环[2.2.1]庚-5-烯-2-羧酸(3 ) 与 4-氧代戊酸 (1) 产生甲二氧代吡咯并 [1,2-a][3,1] 苯并恶嗪 6 和 7，双外类似物得到吡咯并[1,2-a]吡啶 8 作为唯一产物（在4)的情况下，或10连同甲基取代衍生物9(在5的情况下)。化合物 1 与 di-exo-3-aminobicyclo[2.2.1]heptane-2-methanamine (11) 和 di-exo-3-aminobicyclo[2.2.1]hept-5-ene-2-methanamine (12) 反应生成分别得到亚甲基桥连的吡咯并[2,1-b]喹唑啉酮13和14；还分离了含有二吡咯并二氮杂15部分的五环产物。结构和立体化学通过 IR 和 NMR 光谱阐明，包括 COSY、DIFFNOE、DEPT、
• Indoloquinolines, Indolobenzoxazines and Quinazolophthalazines Prepared from Norbornane/eneamino Acids and Hydrazides
  作者：Géza Stájer、Angela E. Szabó、György Túrós、Pál Sohár、Reijo Sillanpää

  DOI：10.1002/ejoc.200500155

  日期：2005.10

  di-exo-aminonorbornane/enecarboxylic acids 1–4 with ethyl 2-(2-oxocyclohexyl)acetate afforded methanoindoloquinolines 5, 6, 8, and 9, the oxo ester participating as a two-membered sp2 building block. In the cases of di-exo- and di-endo-aminonorbornenecarboxylic acids 2 and 4, methanoindolobenzoxazinediones 7 and 10 were also formed; compound 7 was also isolated from the mother liquor of 10. The reactions

  二-内-和双-外-氨基降冰片烷/烯羧酸 1-4 与 2-(2-氧代环己基)乙酸乙酯的反应得到了 methanoindoloquinolines 5、6、8 和 9，氧代酯作为二元 sp2 参与积木。在二外-和双-内-氨基降冰片烯羧酸 2 和 4 的情况下，还形成了 methanoindolobenzoxazinediones 7 和 10；化合物 7 也从 10 的母液中分离出来。 2-(2-氧代环己基)乙酸乙酯与氨基降冰片烷/烯碳酰肼 11-14 的反应产生了 methanoquinazolophthalazines 15-18。化合物的结构通过核磁共振光谱阐明，对于 6、7、8 和 10 也通过 X 射线晶体学阐明。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• The synthesis of pharmacologically important oxindoles <i>via</i> the asymmetric aldol reaction of isatin and the investigation of the organocatalytic activity of new alicyclic β-amino acid derivatives
  作者：Tünde Faragó、Attila M. Remete、István Szatmári、Rita Ambrus、Márta Palkó

  DOI：10.1039/d3ra03528j

  日期：——

  number of novel organocatalysts generated from β-amino acids bearing diendo and diexo norbornene skeletons to improve their catalytic characteristics. The aldol reaction between isatin and acetone selected as the model reaction, was used to test and study enantioselectivities. The potential impact on enantioselectivity control regarding enantiomeric excess (ee%) was probed by varying the reaction parameters

  这项工作涉及由带有二端和二外降冰片烯骨架的β-氨基酸生成的许多新型有机催化剂的合成和后续开发，以改善其催化特性。选择靛红和丙酮之间的羟醛反应作为模型反应，用于测试和研究对映选择性。通过改变反应参数，如添加剂、溶剂、催化剂负载、温度和底物范围，探讨了对映体过量 (ee%) 对对映选择性控制的潜在影响。有机催化剂7生成相应的3-羟基-3-烷基-2-羟吲哚衍生物在 LiOH 存在下具有高达 57% ee 的良好对映选择性。底物筛选用于研究多种取代靛红，结果优异，ee 高达 99%。这项工作的另一个方面涉及采用高速球磨设备进行机械化学研究，以使该模型反应更加环境友好和可持续。
• Stereocontrolled Synthesis of Some Novel Azaheterocyclic β-Amino Ester Stereoisomers with Multiple Stereogenic Centers
  作者：Loránd Kiss、Anas Semghouli、Attila M. Remete、Tamás T. Novák

  DOI：10.1055/a-1877-3822

  日期：2022.10

  The synthesis of some new functionalized azaheterocyclic β-amino esters with multiple stereocenters has been achieved from readily available unsaturated bicyclic β-amino acids by a stereocontrolled synthetic protocol involving N-allylation/propargylation, ring-opening metathesis, and selective ring closure with chemodifferentiation through ring-closing metathesis (RCM). The RCM transformation was investigated

  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。