diacetone galactose | 4064-06-6

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: diacetone galactose
• 英文别名: 1,2:3,4-Di-O-isopropylidene-D-galactopyranose；(4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl)methanol
• CAS: 4064-06-6
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: POORJMIIHXHXAV-UHFFFAOYSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  117 °C/0.015 mmHg (lit.)
• 比旋光度：
  -57.5 º (c=3, CHCl3)
• 密度：
  1.143 g/mL at 25 °C (lit.)
• 溶解度：
  溶于丙酮、氯仿和甲醇。
• 稳定性/保质期：
  **在常温常压下保持稳定**

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2914400090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将产品存放在避光、通风且干燥的地方，并密封保存。

SDS

Name:	1 2:3 4-Di-O-isopropylidene-D-galactopyranose 97% Material Safety Data Sheet
Synonym:	None
CAS:	4064-06-6

Section 1 - Chemical Product MSDS Name:1 2:3 4-Di-O-isopropylidene-D-galactopyranose 97% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4064-06-6	1,2:3,4-Di-O-isopropylidene-D-galactop	97	223-771-7

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: Immediately 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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
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:
Cover with sand, dry lime or soda ash and place in a closed container for disposal. 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. 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# 4064-06-6: 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: Clear liquid
Color: clear, colorless
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 117 deg C @ .01mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: 1.1430g/cm3
Molecular Formula: C12H20O6
Molecular Weight: 260.28

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
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# 4064-06-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,2:3,4-Di-O-isopropylidene-D-galactopyranose - 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# 4064-06-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4064-06-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4064-06-6 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

制备方法与用途

化学性质

双丙酮半乳糖结构中含有一个端位羟基单元和两个缩酮单元，具有较好的化学稳定性。虽然它对碱性物质较为稳定，但对酸性物质相对敏感。其主要的化学性质集中于末端的羟基结构上，可以很容易地通过酯化、加成等反应将糖基单元引入到目标分子中。

应用

双丙酮半乳糖是一种由D-半乳糖和丙酮在酸性物质催化下缩合制备得到的半乳糖衍生物。它常被用作生物化学合成试剂，用于合成糖类有机功能分子。

制备方法

在一个干燥的反应烧瓶中加入36 M H2SO4（16毫升），并将其缓慢滴加到新蒸馏的丙酮（1600毫升）中。需保持反应体系温度在0 °C，然后将溶液升温至室温，并搅拌10分钟。接着，将D-半乳糖（20克，111毫摩尔）加入溶液中并剧烈搅拌18小时。

反应结束后，用无水Na2CO3中和深黄色的溶液，过滤后加入活性炭和Na2CO3（各20克），加热至回流。再次过滤混合物，在旋转蒸发器中浓缩至干燥。通过硅胶柱层析法分离纯化残余物，即可得到目标产物——双丙酮半乳糖。

反应信息

• 作为反应物：
  描述：

  diacetone galactose 以84的产率得到1,2:3,4-Di-O-isopropylidene-6-deoxy-6-tosyl-alpha-D-galactopyranose
  参考文献：
  名称：

  J. Pharm. Sci. 1989, 78, 918-921

  摘要：

  DOI：

文献信息

• Regio‐ and Enantioselective Ni‐Catalyzed Formal Hydroalkylation, Hydrobenzylation, and Hydropropargylation of Acrylamides to α‐Tertiary Amides
  作者：Lou Shi、Ling‐Ling Xing、Wen‐Bo Hu、Wei Shu

  DOI：10.1002/anie.202011339

  日期：2021.1.18

  The development of enantioselective alkyl–alkyl cross‐couplings with coinstantaneous formation of a stereogenic center without the use of sensitive organometallic species is attractive yet challenging. Herein, we report the intermolecular regio‐ and enantioselective formal hydrofunctionalizations of acrylamides, forging a stereogenic center α‐position to the newly formed Csp3–Csp3 bond for the first

  在不使用敏感的有机金属物质的情况下，对映选择性烷基-烷基交叉偶联的发展，即同时形成立体异构中心，这很有吸引力。在此，我们报道了丙烯酰胺的分子间区域和对映体选择性氢官能化，将立体中心α-位置锻造为新形成的C sp3 –C sp3第一次绑定。使用新开发的手性配体可以进行电子逆式形式的加氢官能​​化反应，包括加氢烷基化，加氢苄基化和加氢炔丙基化，从而提供了一种有效的途径，可通过具有易于消旋作用的叔α-立体异构碳中心来获得各种对映体富集的酰胺。这种操作简单的方案可以进行反马尔科夫尼科夫的对映选择性加氢烷基化反应，以及前所未有的加氢苄基化，温和条件下的氢化炔丙基化，具有出色的官能团相容性，可提供多种具有出色对映选择性的酰胺。
• Metal-free visible-light-promoted C(sp³)–H functionalization of aliphatic cyclic ethers using trace O₂
  作者：Ben Niu、Bryan G. Blackburn、Krishnakumar Sachidanandan、Maria Victoria Cooke、Sébastien Laulhé

  DOI：10.1039/d1gc03482k

  日期：——

  Presented is a light-promoted C–C bond forming reaction yielding sulfone and phosphate derivatives at room temperature in the absence of metals or photoredox catalyst. This transformation proceeds in neat conditions through an auto-oxidation mechanism which is maintained through the leaching of trace amounts of O2 as sole green oxidant.

  提出了一种光促进的 C-C 键形成反应，在室温下、在没有金属或光氧化还原催化剂的情况下产生砜和磷酸盐衍生物。这种转化通过自动氧化机制在纯净的条件下进行，该机制通过浸出痕量的O 2作为唯一的绿色氧化剂来维持。
• Facile and selective deprotection of PMB ethers and esters using oxalyl chloride
  作者：Andivelu Ilangovan、Karnambaram Anandhan、Mahabir Prasad Kaushik

  DOI：10.1016/j.tetlet.2015.01.061

  日期：2015.2

  Oxalyl chloride, (0.5 equiv) was found to cleave the PMB group from alkyl, aryl PMB ethers, and esters to give corresponding alcohol and acid in good yields. This method offers simple and efficient protocol for the selective deprotection of PMB ether and ester in DCE at ambient temperature.

  发现草酰氯（0.5当量）可将PMB基团从烷基，芳基PMB醚和酯中裂解出来，从而以高收率得到相应的醇和酸。该方法为环境温度下DCE中PMB醚和酯的选择性脱保护提供了简单有效的方案。
• [EN] MOFEZOLAC DERIVATIVES AS MULTI-FUNCTIONS SELECTIVE COX-1 INHIBITORS<br/>[FR] DÉRIVÉS DE MOFÉZOLAC EN TANT QU'INHIBITEURS SÉLECTIFS À FONCTIONS MULTIPLES DE COX-1
  申请人：UNIVERSITA' DEGLI STUDI DI BARI ALDO MORO

  公开号：WO2017187352A1

  公开（公告）日：2017-11-02

  The invention relates to a new class of compounds of formula (I) targeting COX-1. The invention also relates to the use of some of such compounds as a tool to investigate the structure and function of the enzyme, in the treatment targeting COX-1 or detection of COX-1 in relating disorders or diseases such as cancer and neuroinflammation, in particular in neurological (e.g. autism spectrum disorders) and neurodegenerative diseases (e.g. Alzheimer's diseases, Parkinson's diseases, amyotrophic lateral sclerosis (ALS), multiple sclerosis (MS), traumatic brain injury (TBI), HIV dementia and prion diseases), and in gynecological tumour (e.g. ovarian cancer), neck and head tumor, and haematological tumours (e.g. multiple myeloma) and in the detection of COX-1 in "in vitro" (cells and tissues) and in "in vivo".

  本发明涉及一类新的化合物，其化学式为（I），用于靶向COX-1。本发明还涉及使用其中一些化合物作为研究该酶的结构和功能的工具，在治疗靶向COX-1或检测与癌症和神经炎症等相关的疾病或疾病中的COX-1，特别是在神经学（例如自闭症谱系障碍）和神经退行性疾病（例如阿尔茨海默病，帕金森病，肌萎缩性侧索硬化症（ALS），多发性硬化症（MS），创伤性脑损伤（TBI），HIV痴呆和朊病）以及妇科肿瘤（例如卵巢癌），颈部和头部肿瘤和血液系统肿瘤（例如多发性骨髓瘤）和检测“体外”（细胞和组织）和“体内”的COX-1。
• Tumor-targeted optical contrast agents
  申请人：MALLINCKRODT INC.

  公开号：US20040141920A1

  公开（公告）日：2004-07-22

  Cyanine dye bioconjugates useful for diagnostic imaging and therapy are disclosed. The conjugates include several cyanine dyes with a variety of bis- and tetrakis (carboxylic acid) homologs. The compounds may be conjugated to bioactive peptides, carbohydrates, hormones, drugs, or other bioactive agents. The small size of the compounds allows more favorable delivery to tumor cells as compared to larger molecular weight imaging agents. The various dyes are useful over the range of 350 to 1300 nm, the exact range being dependent upon the particular dye. The use of dimethylsulfoxide helps to maintain the fluorescence of the compounds. The inventive compounds are useful for diagnostic imaging and therapy, in endoscopic applications for the detection of tumors and other abnormalities, for localized therapy, for photoacoustic tumor imaging, detection and therapy, and for sonofluoresence tumor imaging, detection and therapy.

  揭示了用于诊断成像和治疗的青菁染料生物共轭物。这些共轭物包括几种青菁染料，具有各种双和四(羧酸)同系物。这些化合物可以与生物活性肽、碳水化合物、激素、药物或其他生物活性剂结合。与分子量较大的成像试剂相比，这些化合物的小尺寸使其更有利于输送到肿瘤细胞。各种染料在350到1300纳米范围内是有用的，确切范围取决于特定的染料。二甲基亚砜的使用有助于保持化合物的荧光。这些创新的化合物在诊断成像和治疗中很有用，用于内窥镜应用以检测肿瘤和其他异常，用于局部治疗，用于光声肿瘤成像、检测和治疗，以及用于声荧光肿瘤成像、检测和治疗。