3-甲酰基-1H-吲哚-7-羧酸 | 73282-11-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲酰基-1H-吲哚-7-羧酸
• 英文名称: <1-(phenylsulfonyl)indol-2-yl>methanol
• 英文别名: 1-(benzenesulfonyl)-2-(hydroxymethyl)indole；(1-benzenesulfonyl-1H-indol-2-yl)methanol；(1-benzenesulfonyl-indol-2-yl)-methanol；[1-(Phenylsulfonyl)-1H-indol-2-yl]methanol；[1-(benzenesulfonyl)indol-2-yl]methanol
• CAS: 73282-11-8
• 化学式: C₁₅H₁₃NO₃S
• 分子量: 287.339
• InChiKey: LRYLVFIUTJMZBY-UHFFFAOYSA-N

物化性质

• 沸点：
  529.5±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S37/39

SDS

Name:	[1-(Phenylsulfonyl)-1h-indol-2-yl]methanol 95+% Material Safety Data Sheet
Synonym:
CAS:	73282-11-8

Section 1 - Chemical Product MSDS Name:[1-(Phenylsulfonyl)-1h-indol-2-yl]methanol 95+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
73282-11-8	[1-(Phenylsulfonyl)-1H-indol-2-yl]meth	95+%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. 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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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# 73282-11-8: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 76 - 78 deg C
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: C15H13NO3S
Molecular Weight: 287.34

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 73282-11-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
[1-(Phenylsulfonyl)-1H-indol-2-yl]methanol - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 73282-11-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 73282-11-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 73282-11-8 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：

  3-甲酰基-1H-吲哚-7-羧酸 在 sodium hydroxide 、 硫酸 、 氢溴酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 (2R,4R)-2-amino-4-(2-indolyl)methyl pentanedioic acid hydrochloride
  参考文献：
  名称：

  4-取代的D-谷氨酸类似物：具有抗菌活性的第一种有效的谷氨酸消旋酶（MurI）抑制剂。

  摘要：

  描述了显示全细胞抗菌活性的第一种有效的谷氨酸消旋酶（MurI）抑制剂。具有（2R，4S）立体化学并且带有芳基，杂芳基，肉桂基或联芳基甲基取代基的光学纯的4-取代的D-谷氨酸类似物代表一类新型的谷氨酸消旋酶抑制剂。对D-Glu核心的探索导致了对铅化合物（-）-8和10的鉴定。发现2-萘基甲基衍生物10是有效的竞争性谷氨酸消旋酶活性抑制剂（K（i）= 16 nM，圆二色性）分析; IC（50）= 0.1 microg / mL高效液相色谱（HPLC）分析）。彻底的结构-活性关系（SAR）研究导致苯并噻吩衍生物（例如69和74）具有更高的效价（HPLC法分别测定IC（50）= 0.036和0.01 microg / mL）。这些化合物对肺炎链球菌PN-R6表现出强大的全细胞抗菌活性，并且与酶法测定具有良好的相关性。化合物69、74和联芳基衍生物52在体内鼠大腿感染模型中显示抗肺炎链球菌的功效。本

  DOI：

  10.1021/jm020901d
• 作为产物：
  描述：

  N-苯磺酸吲哚 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 3-甲酰基-1H-吲哚-7-羧酸
  参考文献：
  名称：

  4-取代的D-谷氨酸类似物：具有抗菌活性的第一种有效的谷氨酸消旋酶（MurI）抑制剂。

  摘要：

  描述了显示全细胞抗菌活性的第一种有效的谷氨酸消旋酶（MurI）抑制剂。具有（2R，4S）立体化学并且带有芳基，杂芳基，肉桂基或联芳基甲基取代基的光学纯的4-取代的D-谷氨酸类似物代表一类新型的谷氨酸消旋酶抑制剂。对D-Glu核心的探索导致了对铅化合物（-）-8和10的鉴定。发现2-萘基甲基衍生物10是有效的竞争性谷氨酸消旋酶活性抑制剂（K（i）= 16 nM，圆二色性）分析; IC（50）= 0.1 microg / mL高效液相色谱（HPLC）分析）。彻底的结构-活性关系（SAR）研究导致苯并噻吩衍生物（例如69和74）具有更高的效价（HPLC法分别测定IC（50）= 0.036和0.01 microg / mL）。这些化合物对肺炎链球菌PN-R6表现出强大的全细胞抗菌活性，并且与酶法测定具有良好的相关性。化合物69、74和联芳基衍生物52在体内鼠大腿感染模型中显示抗肺炎链球菌的功效。本

  DOI：

  10.1021/jm020901d

文献信息

• Rhodium(II)-Catalyzed Aziridination of Allyl-Substituted Sulfonamides and Carbamates
  作者：Albert Padwa、Andrew C. Flick、Carolyn A. Leverett、Thomas Stengel

  DOI：10.1021/jo048990k

  日期：2004.9.1

  products in high yield. In contrast, the intramolecular aziridination of several cycloalkenyl-substituted carbamates did not require a Rh(II) catalyst and proceeded via an iminoiodinane intermediate. The resulting tricyclic aziridines underwent ring opening when treated with various nucleophiles to give anti-derived products as expected for nucleophilic attack at the three-membered ring. The iodine(III)-mediated

  当用PhI（OAc）2，MgO和催化Rh 2（OAc）4处理时，几种不饱和磺酰胺经过分子内叠氮化，以极好的收率得到双环氮丙啶。在对-TsOH存在下在甲醇中处理所得的氮杂双环磺酰胺，导致氮丙啶环在最取代的位置排他性开放，从而以高收率提供六元和七元环产物。相反，几种环烯基取代的氨基甲酸酯的分子内叠氮化不需要Rh（II）催化剂，而是通过亚氨基碘烷中间体进行的。当用各种亲核试剂处理时，生成的三环氮丙啶类化合物开环，得到抗预期在三元环发生亲核攻击的衍生产物。然而，碘（III）介导的3-吲哚基取代的氨基甲酸酯的反应需要Rh（II）催化剂。预期的氮丙啶中没有观察到，但是C的同时，而螺环3和立体选择性合成中C酰化2发生，得到化合物41，其结构明确地通过X射线结晶研究建立。该反应通过无金属的两性离子中间体以分步方式进行，该中间体被酰胺阴离子同一侧的亲核试剂攻击。2-吲哚基和3-苯并呋喃基取代的氨基甲酸酯均发生相关反应，但立体选择性较低。
• Chiral Anion-Mediated Asymmetric Ring Opening of <i>meso</i>-Aziridinium and Episulfonium Ions
  作者：Gregory L. Hamilton、Toshio Kanai、F. Dean Toste

  DOI：10.1021/ja806431d

  日期：2008.11.12

  traditional asymmetric catalysis based on chiral metals or organocatalysts. We present an enantioselective ring opening of tetrasubstituted meso-aziridinium ions with alcohol nucleophiles proceeding through a chiral ion pair with a binaphthol-phosphate anion. The reaction is initiated by silver-induced ring closure of beta-chloroamines using the Ag salt of the chiral anion as in situ generated catalyst. Use

  通过缺乏路易斯或布朗斯台德碱性位点的阳离子中间体进行的反应对基于手性金属或有机催化剂的传统不对称催化提出了挑战。我们提出了四取代的内消旋氮丙啶离子与醇亲核试剂的对映选择性开环，通过手性离子对与联萘酚-磷酸盐阴离子进行。使用手性阴离子的银盐作为原位生成的催化剂，通过银诱导的 β-氯胺闭环引发反应。使用不溶性 Ag2CO3 作为银源对于获得高对映选择性至关重要；我们相信手性磷酸盐作为“手性阴离子相转移催化剂”将银离子带入有机相。
• 10.1021/acs.joc.4c00571
  作者：Agneswaran, Rudrasenan、Mohanakrishnan, Arasambattu K.

  DOI：10.1021/acs.joc.4c00571

  日期：——

  In this study, we present our findings on the synthesis of α-, β-, γ-carbolines via PIFA/BF3·OEt2-mediated intramolecular cyclization of isomeric azidomethyl(indolyl)acrylates. Alternately, 1,5,7-triazabicyclo[4.4.0]dec-5-ene/1,8-diazabicyclo(5.4.0)undec-7-ene (TBD/DBU)-mediated Michael addition followed by intramolecular cyclization of isomeric 2/3-(azidomethyl)indol-3/2-yl)acrylates also furnished

  在本研究中，我们展示了通过 PIFA/BF 3 ·OEt 2介导的异构叠氮甲基（吲哚基）丙烯酸酯的分子内环化合成 α-、β-、γ-咔啉的研究结果。或者，1,5,7-三氮杂双环[4.4.0]dec-5-ene/1,8-二氮杂双环(5.4.0)十一碳-7-烯 (TBD/DBU) 介导的迈克尔加成，然后进行异构体的分子内环化2/3-(叠氮甲基)吲哚-3/2-基)丙烯酸酯还提供了各自的β-和γ-咔啉衍生物。出乎意料的是，2-(叠氮基甲基)-3-(吲哚-3-基)丙烯酸酯的热解导致通过氮宾插入和重排形成5-(2-(苯基磺酰胺基)芳基)烟酸乙酯以及γ-咔啉和环化。异构2-(叠氮基甲基)-3-(吲哚-2-基)丙烯酸酯热解后产生预期的δ-咔啉。热分子内氮烯插入反应也可以扩展到获得吡啶并苯并噻吩、吡啶并噻吩和喹啉。
• Halogen-Magnesium Exchange Reaction of Iodoindole Derivatives
  作者：Takao Sakamoto、Yoshinori Kondo、Akihiro Yoshida、Shuichiro Sato

  DOI：10.3987/com-95-s31

  日期：——
• Syntheses and Diels-Alder cycloaddition reactions of 4H-furo[3,4-b]indoles. A regiospecific Diels-Alder synthesis of ellipticine
  作者：Gordon W. Gribble、Daniel J. Keavy、Deborah A. Davis、Mark G. Saulnier、Benjamin Pelcman、Timothy C. Barden、Mukund P. Sibi、Erik R. Olson、Joseph J. BelBruno

  DOI：10.1021/jo00048a021

  日期：1992.10

  Seven examples of the novel 4H-furo[3,4-b]indole ring system (3-9)-a stable, synthetic analogue of indole-2,3-quinodimethane-have been synthesized in 6-8 steps from simple indoles in overall yields of 21-28%. These 4H-furo[3,4-b]indoles undergo Diels-Alder reactions with several dienophiles (dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne), including ethyl acrylate, which reacts regiospecifically with furoindole 4 to afford a single carbazole ester (59). This result, predicted by molecular orbital calculations, was used to design and execute a regiospecific Diels-Alder synthesis of the antitumor alkaloid ellipticine (63). Thus, the trimethylsilyl triflate-induced reaction between furoindole 4 and dihydropyridone 68b is greater-than-or-equal-to 99% regioselective and affords lactam 70b in 89% yield. Further manipulation gives ellipticine (63) with no detectable (<1%) isoellipticine (64) in the crude product.