螺[1,3-二氧戊环-2,3'-[3H]吲哚]-2'(1'H)-酮 | 6714-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 螺[1,3-二氧戊环-2,3'-[3H]吲哚]-2'(1'H)-酮
• 中文别名: 吲哚-2(3H)-酮,3,3-伸乙二氧基-
• 英文名称: spiro[1,3-dioxolane-2,3'-indolin]-2'-one
• 英文别名: spiro[indoline-3,2’-[1,3]dioxolan]-2-one；isatin β-ethylene acetal；spiro[[1, 3]dioxolane-2,3′-indolin]-2′-one；spiro[1,3-dioxolane-2,3'-indol]-2'(1'H)-one；spiro[1,3-dioxolane-2,3'-1H-indole]-2'-one
• CAS: 6714-68-7
• 化学式: C₁₀H₉NO₃
• mdl: MFCD00173689
• 分子量: 191.186
• InChiKey: PRMHWSVVQZVDGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R20/21/22
• 海关编码：
  2933990090
• 储存条件：
  2-8℃

SDS

Name:	Spiro-(1 3-dioxolane-2 3 indolin)-2 -one 97% Material Safety Data Sheet
Synonym:
CAS:	6714-68-7

Section 1 - Chemical Product MSDS Name:Spiro-(1 3-dioxolane-2 3 indolin)-2 -one 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
6714-68-7	Spiro-(1,3-dioxolane-2,3'indolin)-2'-o	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
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:

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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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 6714-68-7: 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: tan
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 125 - 128 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: C10H9NO3
Molecular Weight: 191

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 6714-68-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Spiro-(1,3-dioxolane-2,3'indolin)-2'-one - 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
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 6714-68-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 6714-68-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 6714-68-7 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：

  螺[1,3-二氧戊环-2,3'-[3H]吲哚]-2'(1'H)-酮 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 2-(2-tert-Butoxycarbonylamino-phenyl)-[1,3]dioxolane-2-carboxylic acid
  参考文献：
  名称：

  叠氮基叠氮烷的对映选择性合成和关键中间体的选择性官能化。

  摘要：

  已经实现了对映体选择性合成米托烷核（-）-1。关键步骤包括采用闭环复分解快速组装关键的八元环中间体。然后通过使用基于肽的不对称酰基转移催化剂（从候选催化剂的平行筛选中发现）来实现高级仲醇的动力学拆分。然后将光学纯的材料转化为三聚氰胺核，这是选择性修饰的进一步研究的主题，以生产几种含有三聚硅氧烷环系统的取代化合物。

  DOI：

  10.1021/jo0269013
• 作为产物：
  描述：

  2-羟基亚氨基-n-苯乙酰胺 在 硫酸 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.5h， 生成 螺[1,3-二氧戊环-2,3'-[3H]吲哚]-2'(1'H)-酮
  参考文献：
  名称：

  Novel indoline-2,3-dione derivatives as inhibitors of aminopeptidase N (APN)

  摘要：

  Aminopeptidase N (APN/CD13), as a zinc-containing ectoenzyme, plays a critical role in the process of tumor angiogenesis, invasion and metastasis. Through the docking-based virtual screening of chemical databases and the further activity assay, we discovered that compound 10c exhibits potent and selective inhibitory ability towards APN. In addition, a series of indoline-2,3-dione derivates have been designed and synthesized as APN inhibitors. The results of preliminary activity evaluation showed that compound 12a (IC50 = 0.074 +/- 0.0026 mu M) exhibited the best inhibitory activity against APN, which could be used for further anticancer agent research. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.06.024

文献信息

• Strategic synthesis and in vitro antimicrobial evaluation of novel difluoromethylated 1-(1, 3-diphenyl-1H-pyrazol-4-yl)-3, 3-difluoro-1, 3-dihydro-indol-2-ones
  作者：Tejpal Singh Chundawat、Poonam Kumari、Nutan Sharma、Sunita Bhagat

  DOI：10.1007/s00044-016-1658-z

  日期：2016.10

  antifungal activities. Direct fluorination using diethylaminosulfur trifluoride as a nucleophilic fluorinating reagent was carried out in the present paper. Undoubtedly this methodology gives a facile and straightforward pathway to construct 1-(1,3-diphenyl-1H-pyrazol-4-yl)-3,3-difluoro-1,3-dihydro-indol-2-ones in good yields. The structure of new fluorinated 1-(1,3-diphenyl-1H-pyrazol-4-yl)-3,3-difluoro-1

  通过吲哚-2的反应已实现了1-（1,3-二苯基-1 H-吡唑-4-基）-3,3-二氟-1,3-二氢吲哚-2-酮的战略合成。，3-二酮（异丁二烯）和取代的溴乙酰苯，然后环化反应，并评价其体外抗菌和抗真菌活性。本文采用三氟化二乙氨基硫作为亲核氟化剂进行直接氟化。无疑，这种方法为构建1-（1,3-diphenyl-1 H -pyrazol-4-yl）-3,3-difluoro-1,3-dihydro-indol-2-ones高产提供了简便而直接的途径。。基于1 H表征了新的氟化1-（1,3-二苯基-1 H-吡唑-4-基）-3,3-二氟-1,3-二氢-吲哚-2-酮的结构，13 C和19 F核磁共振波谱和质谱数据。通过核Overhauser效应光谱确认目标化合物的结构。一些合成的化合物对细菌和真菌显示出良好的抗菌活性。
• Enantioselective N-alkylation of isatins and synthesis of chiral N-alkylated indoles
  作者：Xiaowei Dou、Weijun Yao、Chunhui Jiang、Yixin Lu

  DOI：10.1039/c4cc04586f

  日期：——

  Asymmetric N-alkylations of isatins with enals were shown to be feasible via a prolinol-catalyzed iminium activation, and N-alkylated isatins and indoles were obtained in good yields and with excellent enantioselectivity.

  通过脯氨醇催化的亚胺活化，显示了使用烯醛对异喹啉进行不对称N-烷基化是可行的，得到了产率较高且具有优异对映选择性的N-烷基化异喹啉和吲哚。
• Synthesis of 2‐(Arylthio)indolenines via Chemoselective Arylation of Thio‐Oxindoles with Arynes
  作者：Adi Saputra、Rong Fan、Tuanli Yao、Jian Chen、Jiajing Tan

  DOI：10.1002/adsc.202000308

  日期：2020.7.16

  A chemoselective S‐ arylation reaction of thio‐oxindoles with arynes is presented. The reaction was performed under mild conditions and provided a straightforward synthesis of 2‐(arylthio)indolenines in good to excellent yields. Besides, this simple operational protocol is not only scalable but also has good functional group compatibilities and substrate scope. Thus, our protocol should allow for the

  化学选择性S-硫代羟吲哚与arynes的芳基化反应被呈现。该反应在温和的条件下进行，可直接合成2-（芳硫基）吲哚胺，收率良好。此外，这种简单的操作协议不仅可扩展，而且具有良好的功能组兼容性和基板范围。因此，我们的方案应允许通过开发硫代亚氨酸酯的新支架来扩展化学空间，而这些支架否则很难合成。
• Synthesis of 1,2,3-benzotriazin-4-one derivatives containing spirocyclic indoline-2-one moieties and their nematicidal evaluation
  作者：Gao-Lei Wang、Xi Chen、Ya-Ning Chang、Dan Du、Zhong Li、Xiao-Yong Xu

  DOI：10.1016/j.cclet.2015.10.024

  日期：2015.12

  Abstract To discover new chemotypes of nematicides with proper toxicological profiles, a series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized and further bioevaluated. The bioassay results showed that most of the synthesized compounds were endowed with moderate to good control efficacy against Meloidogyne incognita at 10.0 mg/L in vivo . Among them, compounds 6k and 6p displayed 100%

  摘要为发现具有适当毒理学特征的杀线虫剂的新化学型，合成了一系列新的1,2,3-苯并三嗪-4-酮衍生物，并对其进行了生物评价。生物测定结果表明，在10.0 mg / L的体内，大多数合成化合物对根结线虫有中等到良好的防治作用。其中，化合物6k和6p在此浓度下表现出100％的抑制活性，这意味着它们可用作潜在的杀线虫剂的先导化合物。
• Environmental Friendly Synthesis of Novel Isatin Ketal and Isatin Schiff Base Derivatives Using Michael Addition Reaction under Solvent-Free Conditions
  作者：Gholamhassan Imanzadeh、Zahra Soltanizadeh、Ali Khodayari、Mohammadreza Zamanloo、Yagoub Mansoori、Jaber Salehzadeh

  DOI：10.1002/cjoc.201100351

  日期：2012.4

  efficient and simple procedure for the synthesis of novel isatin derivatives is described. Michael addition of aniline Schiff bases of isatin or p‐toluidine Schiff bases of isatin to fumaric esters affords the Michael adduct compounds in good to high yields in the presence of K2CO3 and tetrabutylammonium bromide (TBAB) under solvent‐free conditions. Repeating of this reaction about spiro[1,3‐dioxolane‐2,3′‐indol]‐2′(1′H)‐one

  描述了一种合成新的靛红衍生物的有效且简单的方法。在无溶剂条件下，在K 2 CO 3和四丁基溴化铵（TBAB）的存在下，将靛红的苯胺希夫（Schiff）碱或靛蓝的对甲苯胺的席夫（Schiff）碱加至富马酸酯，可使迈克尔加合物以高收率获得高至高收率。重复约螺[1,3-二氧戊环-2,3'-吲哚] -2' - （1'该反应的ħ） -酮，为迈克尔供体，在1,4-二氮杂双环的存在[2.2.2]辛烷（DABCO）在相同条件下以高收率获得迈克尔加合物。