D-樟脑肟 | 13559-66-5

• 物质功能分类: 生物 - 生化试剂盒
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: D-樟脑肟
• 中文别名: 1,7,7-三甲基双环[2.2.1]-2-庚酮肟
• 英文名称: (+/-)-camphor oxime
• 英文别名: Camphor oxime；N-(1,7,7-trimethyl-2-bicyclo[2.2.1]heptanylidene)hydroxylamine
• CAS: 13559-66-5
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: OVFDEGGJFJECAT-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• LogP：
  2.038 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

SDS

Name:	1 7 7-Trimethylbicyclo[2.2.1]heptan-2-one oxime 97% Material Safety Data Sheet
Synonym:
CAS:	13559-66-5

Section 1 - Chemical Product MSDS Name:1 7 7-Trimethylbicyclo[2.2.1]heptan-2-one oxime 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13559-66-5	1,7,7-Trimethylbicyclo[2.2.1]heptan-2-	97%	236-945-2

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
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. May be harmful if swallowed.
Inhalation:
May cause 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.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 13559-66-5: 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: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 110 - 112 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: C10H17NO
Molecular Weight: 167

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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.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13559-66-5: ED6850000 LD50/LC50:
Not available.
Carcinogenicity:
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-one oxime - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 13559-66-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13559-66-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13559-66-5 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：

  D-樟脑肟 在 vanadyl acetylacetonate 双氧水 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以81%的产率得到樟脑
  参考文献：
  名称：

  VO(acac)2 催化氧化去保护肟、腙和缩氨基脲

  摘要：

  在室温下，在丙酮中存在催化量的乙酰丙酮氧钒和过氧化氢的情况下，肟、腙和缩氨基脲容易脱保护。

  DOI：

  10.1081/scc-200039490
• 作为产物：
  描述：

  樟脑 在 吡啶 、 盐酸羟胺 作用下， 反应 2.0h， 以98%的产率得到D-樟脑肟
  参考文献：
  名称：

  (+)-ryanodol的全合成。第三部分。由关键的五环中间体制备 (+)-anhydroryanodol

  摘要：

  本文报告了几项研究，这些研究旨在了解如何将右旋五环关键中间体 5 转化为 (+)-脱水ryanodol (6)。该转化需要 24 个步骤，并通过以下中间体进行：5 → 11 → 19 → 34 → 36 → 39 → 144 → 150 → 6。 关键五环中间体 5 的制备在本系列的第一部分和第二部分报道. 关键词：脱水林根醇，林根醇，二萜，有机合成，策略。

  DOI：

  10.1139/v90-023

文献信息

• Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions
  作者：Zhongzhi Zhu、Xiaodong Tang、Jinghe Cen、Jianxiao Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c8cc00445e

  日期：——

  acetates and xanthates for the synthesis of thiazol-2-yl ethers with remarkable regioselectivity has been developed. Various oxime acetates, whether derived from aryl ketones or alkyl ketones, or natural product cores are suitable for this conversion. Unique dihydrothiazoles were also obtained when both reaction sites were methine. Mechanistic studies indicated that imino copper(III) intermediates were involved

  新型的铜催化的肟肟酸酯和黄药酸酯的环化反应用于合成噻唑-2-基醚，具有显着的区域选择性。各种衍生自芳基酮或烷基酮的乙酸肟酯，或天然产物核均适用于该转化。当两个反应位点均为次甲基时，也获得了独特的二氢噻唑。机理研究表明，涉及亚氨基铜（III）中间体。另外，该方案在氧化还原中性条件下进行，不需要添加剂或配体。
• Pyrazine-based polymeric complex of oxodiperoxochromium (VI) compound as a new stable, mild, efficient and versatile oxidant in organic synthesis
  作者：Bahman Tamami、Hamid Yeganeh

  DOI：10.1016/s0040-4020(97)00461-4

  日期：1997.6

  this reagent alcohols are converted to the corresponding carbonyl compounds. With 1,2-dioles CC bond cleavage occurs. Decarboxylation of α-hydroxy acids proceeds quantitatively. Also thiols are converted to disulfides, hydroxy phenols to quinones, benzylamines to carbonyl compounds, tertiaryamines to the N-oxides, phosphines to phosphine oxides, sulfides to sulfoxides, and anthracene and phenanthrene

  通过常规方法制备并表征标题化合物。描述了其用作多种有机化合物的化学计量氧化剂的用途。用这种试剂将醇转化为相应的羰基化合物。对于1,2-二醇，CC键发生裂解。α-羟基酸的脱羧定量地进行。硫醇也被转化为二硫化物，羟基苯酚被转化为醌，苄胺被转化为羰基化合物，叔胺被转化为N-氧化物，膦被转化为氧化膦，硫化物被转化为亚砜，蒽和菲被转化为醌。肟的脱保护和甲硅烷基醚的氧化脱保护很容易进行。
• Regeneration of carbonyl compounds by cleavage of CN bonds under mild and completely heterogeneous conditions
  作者：F Shirini、M.A Zolfigol、A Safari、I Mohammadpoor-Baltork、B.F Mirjalili

  DOI：10.1016/j.tetlet.2003.08.031

  日期：2003.9

  Oximes, hydrazones, semicarbazones and azines are converted to the corresponding carbonyl compounds using a combination of Zr(HSO4)4 and wet SiO2 in good to high yields under completely heterogeneous conditions.

  使用Zr（HSO 4）4和湿SiO 2的组合，可以在完全非均质条件下以高至高收率将肟、,、半咔唑和嗪转化为相应的羰基化合物。
• ALANINE/CHLOROCHROMIC ACID/SILICA GEL: AN EFFICIENT AND SELECTIVE REAGENT FOR THE OXIDATION OF ORGANIC FUNCTIONAL GROUPS
  作者：Peyman Salehi、Mohammad Mehdi Khodaei、Amin Rostami

  DOI：10.1080/10426500490475102

  日期：2004.11.1

  Alanine/chlorochromic acid/silica gel is a new and selective reagent for the efficient oxidation of sulfides, thiols, oximes, and alcohols. Oxidation of sulfides is solvent dependent. In chloroform at room temperature sulfoxides are formed as the major products, while in carbon tetrachloride or under solvent-free conditions solfones are produced in good-to-excellent yields.

  丙氨酸/氯铬酸/硅胶是一种用于有效氧化硫化物、硫醇、肟和醇的新型选择性试剂。硫化物的氧化取决于溶剂。在室温下在氯仿中形成亚砜作为主要产物，而在四氯化碳或无溶剂条件下，以良好至极好的收率生产四氢呋喃。
• Beckmann Rearrangement of Oximes Catalyzed with Tetrabutylammonium Perrhenate and Trifluoromethanesulfonic Acid
  作者：Hiroyuki Kusama、Yuko Yamashita、Koichi Narasaka

  DOI：10.1246/bcsj.68.373

  日期：1995.1

  The Beckmann rearrangement of oximes is catalyzed by a combined use of tetrabutylammonium perrhenate (Bu4NReO4) and trifluoromethanesulfonic acid in nitromethane under azeotropic conditions, giving amides in high yield. By employing this catalytic system, amides can be prepared directly from ketones and hydroxylamine hydrochloride.

  肟的贝克曼重排由高铼酸四丁基铵 (Bu4NReO4) 和三氟甲磺酸在共沸条件下在硝基甲烷中的组合使用催化，得到高产率的酰胺。通过使用这种催化体系，可以直接从酮和盐酸羟胺制备酰胺。

表征谱图