2-异丁吲哚丁醇 | 13574-84-0

• 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: 2-异丁吲哚丁醇
• 中文别名: Na-叔丁氧羰基-L-谷氨酸γ-苄酯二环乙胺盐
• 英文名称: Boc-Glu(OBzl)-OH*DCHA
• 英文别名: Boc-Glu(OBzl)*DCHA；Boc-glu(obzl)-oh dcha；N-cyclohexylcyclohexanamine;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-phenylmethoxypentanoic acid
• CAS: 13574-84-0
• 化学式: C₁₂H₂₃N*C₁₇H₂₃NO₆
• 分子量: 518.694
• InChiKey: PLGYLOMCRIZGSY-ZOWNYOTGSA-N

物化性质

• 熔点：
  140-142 °C

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 海关编码：
  2924299090
• 安全说明：
  S22,S24/25

SDS

Name:	BOC-L-Glutamic Acid-5-Benzylester DCHA 99.5+% Material Safety Data Sheet
Synonym:	None known
CAS:	13574-84-0

Section 1 - Chemical Product MSDS Name:BOC-L-Glutamic Acid-5-Benzylester DCHA 99.5+% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13574-84-0	BOC-L-Glutamic Acid-5-Benzylester DCHA	99.5+	237-008-0

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. Keep refrigerated. (Store below 4C/39F.)

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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# 13574-84-0: 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: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 141.00 - 143.00 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:
Specific Gravity/Density:
Molecular Formula: C17H23NO6.C12H23N
Molecular Weight: 518.69

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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:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13574-84-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
BOC-L-Glutamic Acid-5-Benzylester DCHA - 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# 13574-84-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13574-84-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13574-84-0 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：

  2-异丁吲哚丁醇 在 盐酸 、 1-羟基苯并三唑 、 对甲苯磺酸 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 Boc-Glu(OBzl)3-OBzl
  参考文献：
  名称：

  单个 α-螺旋多肽链上的光诱导电子转移

  摘要：

  在 etudie le transfert d'electron intramoleculaire le long de l'helice α dupeptide 上的固定组发色团 sur des 多肽（contenant surtout des glutamates）。练习曲 est effectuee sur le肽模型 Boc-dmaPhe-Ala-pyr Ala-OMe

  DOI：

  10.1021/ja00199a044
• 作为产物：
  描述：

  L-谷氨酸 在 硫酸 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 23.0h， 生成 2-异丁吲哚丁醇
  参考文献：
  名称：

  Leibfritz, Dieter; Brunne, Roger M.; Weihrauch, Thomas, Liebigs Annalen der Chemie, 1989, p. 1017 - 1028

  摘要：

  DOI：

文献信息

• Synthesis of .ALPHA.- and .GAMMA.-(N-carbobenzoxy- and N-tert-butyloxycarbonyl-L-glutamyl)cholines.
  作者：MATAO KANAOKA、YUJI HORIKAWA、HARUHIKO KUGO、YOSHITO NISHIZAWA

  DOI：10.1248/cpb.33.5062

  日期：——

  In order to examine the lipotropic and hypotensive effects of glutamylcholines, α-and γ-(Z-and Boc-glutamyl) cholines (4a, 4'a, 4b and 4'b) were synthesized by the removal of the tert-butyl and benzyl groups of the corresponding tert-butyl (3a and 3'a) and benzyl (3b and 3'b) choline esters which were obtained by the esterification of tert-butyl Z-glutamates (1a and 1'a) and benzyl Boc-glutamate dicyclohexylamine salts (1b and 1'b) with N, N-dimethylaminoethyl chloride, followed by methylation with methyl halide.

  为了研究谷氨酰胆碱的利胆和降压作用，通过去除相应的叔丁基（3a和3'a）和苄基（3b和3'b）胆碱酯中的叔丁基和苄基，合成了α-和γ-（Z-和Boc-谷氨酰）胆碱（4a, 4'a, 4b和4'b）。这些胆碱酯是通过叔丁基Z-谷氨酸盐（1a和1'a）和苄基Boc-谷氨酰二环己胺盐（1b和1'b）与N,N-二甲氨基乙基氯化物的酯化反应制备的，随后用甲基卤进行甲基化。
• The hydrolysis of primary amide groups in Asn/Gln-containing peptides
  作者：V. V. Onoprienko、E. A. Yelin、A. I. Miroshnikov

  DOI：10.1007/bf02758662

  日期：2000.6

  Peptides Boc-Ala-Asn/Gln-OH and Boc-Asn/Gln-Ala-OH were saponified with barium hydroxide to corresponding Asp/Glu-containing peptides. Under the conditions of saponification, Boc-Asn-Ala-OH additionally afforded Boc-Asp-OH, isopeptide Boc-Asp(Ala)-OH, and Boc-NHSuc>Ala-OH, with the third being the key intermediate in these transformations. Boc-Asp(OMe)-Ala-OMe underwent similar transformations under

  肽 Boc-Ala-Asn/Gln-OH 和 Boc-Asn/Gln-Ala-OH 用氢氧化钡皂化成相应的含 Asp/Glu 的肽。在皂化条件下，Boc-Asn-Ala-OH额外得到Boc-Asp-OH、异肽Boc-Asp(Ala)-OH和Boc-NHSuc>Ala-OH，其中第三个是这些转化的关键中间体. Boc-Asp(OMe)-Ala-OMe 在用重氮甲烷或三乙胺处理下经历了类似的转化。氢氧化钡皂化伴随着 N 端氨基酸残基的高度差向异构化，而 Boc-Asp(OMe)-Ala-OMe 重氮甲烷处理的产物具有低度差向异构化。
• Synthesis of Peptides Containing ?,?-Disubstituted ?-Amino Acids by the Azirine/Oxazolone Method: The (12-20)-Nonapeptide of the Ionophore Alamethicin
  作者：Peter Wipf、Heinz Heimgartner

  DOI：10.1002/hlca.19900730103

  日期：1990.1.31

  The (12–20)-nonapeptide Z-Leu-Aib-Pro-Val-Aib-Aib-Glu (OBzl)-Gln-Pheol (10) of the ionophor alamethicin was synthesized by a new strategy, using 3-amino-2,2-dimethyl-2H-azirines 2 as synthons for the α-aminoisobutyric acid (Aib) moieties.

  用新的策略，使用3-氨基-2合成了ionophor alamethicin的（12–20）-九肽Z-Leu-Aib-Pro-Val-Aib-Aib-Glu（OBzl）-Gln-苯酚（10）作为α-氨基异丁酸（Aib）部分的合成子，2-2-二甲基-2 H -azirines 2。
• Synthese eines membranmodifizierenden Alamethicin-analogen Nonadekapeptids
  作者：Raymond Oekonomopulos、Günther Jung

  DOI：10.1002/jlac.197919790811

  日期：1979.8.29

  Vorstellungen über die Wirkungsweise von Alamethicin und dessen Konformation wurde das Nonadekapeptid 14a aus den kristallinen, analytisch reinen und durch 13C-NMR- sowie CD-Spektroskopie untersuchten Fragmenten A bis D wie folgt aufgebaut: Boc-Gly11-Ala-Aib-Ala-Aib5-OH (A, 8b) wurde mit H-Ala6-Aib-Ala-Aib-Ala10-OMe (B, 9c) und Boc-Gly11-Ala-Aib13-OH (C, 5b) mit H-Pro14-Ala-Aib-Aib-Glu(OBzl)-Gln19-OMe (D, 10c)

  九肽Boc-（Aib-L-Ala）5 -Gly-Ala-Ala-Pro-Ala-Aib-Aib-Glu（OBzl）-Gln-OMe（14a），其衍生物14b中带有游离谷氨酸羧基18位和六肽Boc-（Aib-L-Ala）5-Pro-Ala-Aib-Aib-Glu（OBzl）-Gln-OMe（13a）通过片段缩合合成。对于二肽和三肽片段的制备，与氯碳酸异丁酯混合酸酐的偶联被证明特别有用，而较大的片段通过二环己基碳二亚胺/ 1-羟基苯并三唑偶联而连接。基于关于乐果霉素的作用方式及其构象的想法，由13 C-NMR和CD光谱法分析的结晶纯净片段A至D构成了九肽14a，如下所示：Boc-Gly 11 -Ala-Aib -将Ala-Aib 5 -OH（A，8b）与H-Ala 6 -Aib-Ala-Aib-Ala 10 -OMe（B，9c）和与H-Pro 14 -Ala-Aib-Aib-Glu（OBzl）-Gln
• Novel amino acid derivatives
  申请人：Ono Pharmaceutical Co., Ltd.

  公开号：US05017589A1

  公开（公告）日：1991-05-21

  The compounds of the formula: ##STR1## (wherein R.sup.1 is hydrogen or alkyl; R.sup.2 is carbocyclic or heterocyclic ring, unsubstituted or substituted by R.sup.3 S; R.sup.3 is halogen, trihalomethyl, hydroxy, alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfornyl, cyano, nitro, or group of the formula: --C.sub.6 H.sub.4 --R.sup.4, --NR.sup.5 R.sup.6, --CO--R.sup.7, --COOR.sup.8, --CONR.sup.5 R.sup.6, --SO.sub.2 NR.sup.5 R.sup.6 or --NHCO--R.sup.7, in which R.sup.4 is hydrogen, halogen, trihalomethyl, hydroxy, alkyl or alkoxy, R.sup.5 and R.sup.6 are each hydrogen or alkyl, R.sup.7 is alkyl or phenyl substituted by R.sup.4 and R.sup.8 is hydrogen or alkyl; Z is hydrogen or group of the formula: --COR.sup.9, ##STR2## in which R.sup.9 is alkyl or phenyl substituted by R.sup.10, in which R.sup.10 is hydrogen, halogen, trihalomethyl, alkyl or alkoxy, R.sup.11 and R.sup.12 are each hydrogen, alkyl or phenyl substituted by R.sup.10, or R.sup.11 and R.sup.12 together represent alkylene and p is 1 or 2; .circle. is phenyl or cycloalkyl substituted by R.sup.13 in which R.sup.13 is hydrogen, halogen, trihalomethyl, alkyl or alkoxy; and m is zero and n is 1 to 4 or n is zero and m is 1 to 4; and non-toxic salts thereof have inhibitory effect on enkephalinase, and therefore, are useful as analgesic, antianxiety and anticonvulsant.

  该式化合物的结构为：##STR1##（其中R.sup.1为氢或烷基；R.sup.2为碳环或杂环，未取代或被R.sup.3 S取代；R.sup.3为卤素、三卤甲基、羟基、烷基、烷氧基、烷硫基、烷基亚砜基、烷基磺酰基、氰基、硝基，或者为--C.sub.6 H.sub.4 --R.sup.4、--NR.sup.5 R.sup.6、--CO--R.sup.7、--COOR.sup.8、--CONR.sup.5 R.sup.6、--SO.sub.2 NR.sup.5 R.sup.6或--NHCO--R.sup.7的基团，在其中R.sup.4为氢、卤素、三卤甲基、羟基、烷基或烷氧基，R.sup.5和R.sup.6均为氢或烷基，R.sup.7为烷基或被R.sup.4取代的苯基，R.sup.8为氢或烷基；Z为氢或者--COR.sup.9的基团，##STR2##其中R.sup.9为烷基或被R.sup.10取代的苯基，其中R.sup.10为氢、卤素、三卤甲基、烷基或烷氧基，R.sup.11和R.sup.12均为氢、烷基或被R.sup.10取代的苯基，或者R.sup.11和R.sup.12一起表示亚烷基，p为1或2；.circle.为被R.sup.13取代的苯基或环烷基，其中R.sup.13为氢、卤素、三卤甲基、烷基或烷氧基；m为零，n为1至4，或者n为零，m为1至4；其无毒盐具有对脑啡肽酶的抑制作用，因此，可用作镇痛剂、抗焦虑剂和抗抽搐剂。