2-三甲基甲硅烷基-N-叔丁基乙酰胺 | 73198-78-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-三甲基甲硅烷基-N-叔丁基乙酰胺
• 英文名称: trimethylsilylacetaldehyde tert-butylimine
• 英文别名: N-tert-Butyl-2-(trimethylsilyl)acetaldimine；2-(trimethylsilyl)acetaldehyde tert-butylimine；2-Trimethylsilyl-N-tert-butylacetaldimine；N-tert-butyl-2-trimethylsilylethanimine
• CAS: 73198-78-4
• 化学式: C₉H₂₁NSi
• 分子量: 171.358
• InChiKey: FBKXKUUGFCDLGG-UHFFFAOYSA-N

物化性质

• 沸点：
  54 °C (12 mmHg)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 安全说明：
  S24/25

SDS

Name:	2-TRIMETHYLSILYL-N-TERT-BUTYLACETALDIMINE Material Safety Data Sheet
Synonym:
CAS:	73198-78-4

Section 1 - Chemical Product MSDS Name:2-TRIMETHYLSILYL-N-TERT-BUTYLACETALDIMINE Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
73198-78-4	2-TRIMETHYLSILYL-N-TERT-BUTYLACETALDIM		unlisted

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.
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.
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 extinguishing media most appropriate for the surrounding fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable 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 tightly closed container. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 73198-78-4: 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: Liquid
Color: light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 54 deg C @ 12.00mm
Freezing/Melting Point: Not available.
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:
Molecular Weight: 171.36

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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:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 73198-78-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-TRIMETHYLSILYL-N-TERT-BUTYLACETALDIMINE - 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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 73198-78-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 73198-78-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 73198-78-4 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：

  2-三甲基甲硅烷基-N-叔丁基乙酰胺 在 zinc dibromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 8.75h， 生成 (2E)-N-tert-butyl-5-methylhexa-2,4-dien-1-imine
  参考文献：
  名称：

  A simple and highly stereoselective route to E-.alpha.,.beta.-unsaturated aldehydes

  摘要：

  Zinc bromide mediated reaction of alpha,alpha-bis(trimethylsilyl)-tert-butylacetaldimine (3) with a wide range of aldehydes takes place under mild conditions and affords the corresponding alpha,beta-unsaturated aldehydes in good yields and with very high E stereoselectivity (>98%). This procedure is successfully applied to the preparation of intermediates for retinoid and natural product synthesis.

  DOI：

  10.1021/jo00061a027
• 作为产物：
  描述：

  叔丁胺 、 三甲基乙炔基硅 在 bis(diethylamido)[N-(2,6-diisopropylphenyl)benzamidato]Ti 1,3,5-三甲氧基苯 作用下， 以 氘代苯 为溶剂， 反应 24.0h， 以78%的产率得到2-三甲基甲硅烷基-N-叔丁基乙酰胺
  参考文献：
  名称：

  抗马尔科夫尼科夫分子间加氢胺化反应：一种双（氨基甲酸酯）钛预催化剂，用于制备反应性醛亚胺。

  摘要：

  [反应：见正文]大量的双（N-2'，6'-二异丙基苯基（苯基）-氨基甲酸酯）钛-双（二乙基酰胺基）配合物被确定为一种高活性和区域选择性的催化剂，可用于广泛的抗马尔可夫尼科夫加氢胺化反应范围的末端烷基炔烃与烷基胺。该钛配合物已得到充分表征，包括其X射线晶体结构。使用一锅法进一步精制了生成的反应性醛亚胺产品，以提供取代的胺，醛和异喹啉骨架。

  DOI：

  10.1021/ol0359214

文献信息

• Total Synthesis of the Novel Immunosuppressant Sanglifehrin A
  作者：K. C. Nicolaou、F. Murphy、S. Barluenga、T. Ohshima、H. Wei、J. Xu、D. L. F. Gray、O. Baudoin

  DOI：10.1021/ja994285v

  日期：2000.4.1

  The total synthesis of the novel immunosuppressant sanglifehrin A (SFA, 1) is described. The approach is flexible, convergent, and stereoselective. The use of Paterson's aldol methodology was pivotal for the preparation of the novel, highly substituted spirolactam fragment of SFA. The 22-membered macrocyclic core of the molecule and the coupling of this fragment to the spirolactam moiety were successfully

  描述了新型免疫抑制剂 sanglifehrin A (SFA, 1) 的全合成。该方法是灵活的、收敛的和立体选择性的。Paterson 的羟醛方法的使用对于制备新型的、高度取代的 SFA 螺内酰胺片段至关重要。分别使用选择性分子内和分子间 Stille 反应成功实现了分子的 22 元大环核心以及该片段与螺内酰胺部分的偶联。基于碳二亚胺的方案被用于合成三肽骨架。
• Application of stereocontrolled aldol coupling to synthesis of segments of immunosuppressants FK-506 and rapamycin
  作者：James D. White、Jörg Deerberg、Steven G. Toske、Takayuki Yakura

  DOI：10.1016/j.tet.2009.06.030

  日期：2009.8

  The sector comprising C24–C34 of FK-506 containing five of the stereogenic centers in this macrolide was synthesized from (−)-quinic acid. Aldol coupling of the C24–C34 unit with a methyl ketone representing C20–C23 of FK-506 proceeded with complete Felkin stereoselectivity to afford the C20–C34 portion of the immunosuppressant. A chelate transition state invoking coordination of a lithium enolate

  由（-）-奎尼酸合成了包含FK-506的C24-C34的区域，该区域在该大环内酯中包含五个立体异构中心。将C24–C34单元与代表FK-506的C20–C23的甲基酮进行Aldol偶联，以完全的Felkin立体选择性进行，得到免疫抑制剂的C20–C34​​部分。提出了一种使烯醇酸锂与三苯甲基醚配位的螯合过渡态来解释这种立体选择性。FK-506的C26-C34部分构建所采用的策略已扩展到雷帕霉素的C34-C42亚基。使用Mukaiyama不对称抗醛醇偶合剂将大环内酯C26-C33片段中C27,28处的邻二醇功能固定到位。
• Retinoic acid analogs. Synthesis and potential as cancer chemopreventive agents
  作者：Marcia I. Dawson、Peter D. Hobbs、Karl Kuhlmann、Victor A. Fung、C. Tucker Helmes、Wan-Ru Chao

  DOI：10.1021/jm00183a010

  日期：1980.9

  Analogues of retinoic acid have been synthesized as potential chemopreventive agents against epithelial cancer. Ethyl (E)-9-(2-norbornenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate (9), (E)-3,7-dimethyl-9-(2-ethyl-6,6-dimethyl-1-cyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid (25), and 2-(2'-methoxyethoxy)ethyl retinoate (26) displayed good activity in the inhibition of tumor promoter-induced mouse epidermal

  视黄酸的类似物已被合成为潜在的针对上皮癌的化学预防剂。（E）-9-（2-降冰片烯基）-3,7-二甲基壬娜-2,4,6,8-四烯酸酯（9），（E）-3,7-二甲基-9-（2-乙基-6） 1,6-二甲基-1-环己烯-1-基）壬二-2,4,6,8-丁烯酸（25）和2-（2'-甲氧基乙氧基）视黄酸乙酯（26）在抑制甲壳素方面表现出良好的活性。肿瘤启动子诱导的小鼠表皮鸟氨酸脱羧酶测定。（E）-1-（3-乙酰氧基苯基）-4-甲基-6-（2,6,6-三甲基-1-环己烯-1-基）hexa1,3,5-三烯（34）的活性低。（E）-5- [2,6-二甲基-8-（2,6,6-三甲基-1-环己烯-1-基）辛基-1,3,5,7-四烯-1-基]四唑（ 40）不活跃。
• Design, Synthesis, and Biological Evaluation of a 1α,25-Dihydroxy-19-norvitamin D₃ Analogue with a Frozen A-Ring Conformation
  作者：Rafal R. Sicinski、Agnieszka Glebocka、Lori A. Plum、Hector F. DeLuca

  DOI：10.1021/jm070635+

  日期：2007.11.1

  reduced activity compared to the natural hormone 1, but the binding, differentiation, and transcriptional activities of analogue 5 are markedly higher than that of 4 constrained in the alpha-chair conformation. Surprisingly, in vivo tests in mice showed that the analogue 4 significantly increases serum calcium at dose levels similar to 1alpha,25-(OH)2D3. These seemingly discordant results are discussed

  为了建立负责生物活性的维生素D化合物的构象，合成了具有沿轴向固定的1α-羟基（β椅子形式）的1alpha，25-二羟基-19-降钙素D类似物4。起始化合物为衍生自奎宁酸内酯的双环内酯6、7a和7b，它们被转化为双环酮13。该化合物与砜15的Julia偶联生成了19-norvitamin D类似物4，具有一个额外的环。连接3beta-氧和C-2，以及异构体3beta-羟基化合物5。在体外，与天然激素1相比，类似物4和5的活性都降低了，但是类似物5的结合，分化和转录活性却很高。明显高于受alpha-chair构象约束的4个。出奇，小鼠体内试验显示，类似物4以与1alpha，25-（OH）2D3相似的剂量水平显着增加血清钙。讨论了这些看似不一致的结果。
• Synthesis and binding studies of a photoaffinity label for bovine rhodopsin
  作者：Ranjan Sen、John D. Carriker、Valeria Balogh-Nair、Koji Nakanishi

  DOI：10.1021/ja00375a048

  日期：1982.6