(1S,2S,4S)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯 | 321744-19-8

• 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
• 中文名称: (1S,2S,4S)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯
• 中文别名: (1S,2S,4S)-N-1-氨基-2-羟基环戊烷-4-羧酸甲酯
• 英文名称: (1S,2S,4S)-1-(tert-butoxycarbonylamino)-2-hydroxycyclopentane-4-carboxylic acid methyl ester
• 英文别名: (1S,3S,4S)-3-tert-butoxycarbonylamino-4-hydroxycyclopentanecarboxylic acid methyl ester；methyl (1S,3S,4S)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentane-1-carboxylate
• CAS: 321744-19-8
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: SSATZBUCOTXXGA-CIUDSAMLSA-N

物化性质

• 熔点：
  71.2 °C
• 沸点：
  402.56°C (rough estimate)
• 密度：
  1.1623 (rough estimate)
• 稳定性/保质期：
  <p>遵照规定使用和储存，则不会分解。</p>

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25

SDS

Name:	(1S 2S 4S)-N-BOC-1-Amino-2-Hydroxycyclopentane-4-Carboxylic Acid Material Safety Data Sheet
Synonym:	Methyl (1S,3S,4S)-N-BOC-3-Amino-4-Hydroxycyclopentanecarboxylate
CAS:	321744-19-8

Section 1 - Chemical Product MSDS Name:(1S 2S 4S)-N-BOC-1-Amino-2-Hydroxycyclopentane-4-Carboxylic Acid Material Safety Data Sheet
Synonym:Methyl (1S,3S,4S)-N-BOC-3-Amino-4-Hydroxycyclopentanecarboxylate

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
321744-19-8	(1S,2S,4S)-N-BOC-1-Amino-2-Hydroxycycl	95%	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. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
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. 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.

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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:
Wash thoroughly after handling. Use with adequate ventilation.
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.
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# 321744-19-8: 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: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C12H21NO5
Molecular Weight: 259.3

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Incompatible materials, dust generation.
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# 321744-19-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1S,2S,4S)-N-BOC-1-Amino-2-Hydroxycyclopentane-4-Carboxylic - 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.
WGK (Water Danger/Protection)
CAS# 321744-19-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 321744-19-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 321744-19-8 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：

  (1S,2S,4S)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯 在 盐酸 作用下， 反应 5.0h， 生成 (1S,3S,4S)-3-Amino-4-hydroxy-cyclopentanecarboxylic acid
  参考文献：
  名称：

  将氨基环戊烷羧酸接枝到RGD三肽序列上会产生低纳摩尔浓度的alphaVbeta3 / alphaVbeta5整联蛋白双结合剂。

  摘要：

  以手性非外消旋形式制备了11个γ-氨基环戊烷羧酸（Acpca）平台，包括四个二羟基代表分子（19-22），三个羟基类似物（34-36）和四个脱氧衍生物（30-33）。然后通过混合固相/溶液方案将这些简单的单元嫁接到Arg-Gly-Asp（RGD）三肽构架上，从而提供11种环-[-Arg-Gly-Asp-Acpca-]型大环类似物的集合体-11。评价各个化合物对αVbeta3和αVbeta5整联蛋白受体的结合亲和力。与参考化合物EMD121974和ST1646相比，类似物10表现出非常有趣的活性谱（IC50 / alphaVbeta3 = 1.5 nM； IC50 / alphaVbeta5 = 0.59 nM）。密切相关的同类物6、8 和9也被证明是出色的双重粘合剂，其活性水平在低纳摩尔范围内。确定了三维（3D）NMR溶液结构，并在选定的类似物上与参照化合物EMD121974进行了整合素α

  DOI：

  10.1021/jm050698x
• 作为产物：
  描述：

  2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 4-二甲氨基吡啶 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene(cyclooctadiene)rhodium(I) tetrafluoroborate 、 lactamase 、 TEA 、 氢气 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、517.11 kPa 条件下， 反应 4.0h， 生成 (1S,2S,4S)-N-Boc-1-氨基-2-羟基环戊烷-4-羧酸甲酯
  参考文献：
  名称：

  An efficient route to all eight stereoisomers of a tri-functionalised cyclopentane scaffold for drug discovery

  摘要：

  A route to all eight stereoisomers of 3-(tert-butoxycarbonylamino)-4-hydroxycyclopentanecarboxylic acid methyl ester is presented; these products should prove to be valuable scaffolds in pharmaceutical discovery. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00108-2

文献信息

• Use of hydrolases for the synthesis of cyclic amino acids
  作者：Richard C Lloyd、Michael C Lloyd、Mark E.B Smith、Karen E Holt、Jonathan P Swift、Philip A Keene、Stephen J.C Taylor、Raymond McCague

  DOI：10.1016/j.tet.2003.10.116

  日期：2004.1

  The synthesis of several cyclic amino acids that have all the necessary structural features to make them ideal scaffolds for use in medicinal chemistry is described. A key step in each synthesis is the use of hydrolase enzymes to define a chiral centre. In order to elaborate these building blocks into more complex molecules, crystallization and asymmetric hydrogenation were used to define further stereocentres

  描述了具有所有必要结构特征以使其成为用于药物化学的理想支架的几种环状氨基酸的合成。每个合成过程中的关键步骤是使用水解酶来定义手性中心。为了将这些结构单元详细化为更复杂的分子，使用了结晶和不对称氢化来定义进一步的立体中心。
• Factor Xa inhibitors
  申请人：Zbinden Groebke Katrin

  公开号：US20070049587A1

  公开（公告）日：2007-03-01

  The invention is concerned with novel cycloalkane carboxamides of formula (I) wherein X, X 1 , Y, Y 1 , R 1′ , R 1″ , R 2 , R 3 , m and n are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit the coagulation factor Xa and can be used as medicaments.

  这项发明涉及一种新颖的环烷基羧酰胺，其化学式为（I），其中X、X1、Y、Y1、R1'、R1"、R2、R3、m和n如说明书和权利要求中所定义，并且其生理上可接受的盐。这些化合物抑制凝血因子Xa，并可用作药物。
• NOVEL CYCLOALKANE CARBOXAMIDES AS FACTOR XA INHIBITORS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1928864A1

  公开（公告）日：2008-06-11
• US7678917B2
  申请人：——

  公开号：US7678917B2

  公开（公告）日：2010-03-16
• [EN] NOVEL CYCLOALKANE CARBOXAMIDES AS FACTOR XA INHIBITORS<br/>[FR] NOUVEAUX CYCLOALCANECARBOXAMIDES EN TANT QU'INHIBITEURS DU FACTEUR XA
  申请人：HOFFMANN LA ROCHE

  公开号：WO2007025949A1

  公开（公告）日：2007-03-08

  [EN] The invention is concerned with novel cycloalkane carboxamides of Formula (I) wherein X, X¹, Y, Y^1', R^1'', R¹, R², R³, m and n are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds inhibit the coagulation factor Xa and can be used as medicaments.
  [FR] La présente invention concerne de nouveaux cycloalcanecarboxamides de Formule (I) où X, X¹, Y, Y^1', R^1'', R¹, R², R³, m et n sont tels que définis dans la description et dans les revendications, de même que des sels de qualité physiologique desdits composés. Ces composés inhibent le facteur de coagulation Xa et peuvent être employés en tant que médicaments.