苄氧基乙醛二甲基乙缩醛 | 127657-97-0

• 物质功能分类: 有机原料 - 醛类化合物
• 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: 苄氧基乙醛二甲基乙缩醛
• 英文名称: 2-benzyloxy-1,1-dimethoxyethane
• 英文别名: benzyloxyacetaldehyde dimethyl acetal；2,2-dimethoxyethoxymethylbenzene
• CAS: 127657-97-0
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: QITBBLPNYKECAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  80-82°C 0,5mm
• 密度：
  1,035 g/cm3
• 闪点：
  80-82°C/0.5mm
• 稳定性/保质期：

  如果按照规格使用和储存，就不会分解，也未有已知危险反应。请避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S24/25
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉、干燥处。同时，确保工作环境有良好的通风或排气设施。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Benzyloxyacetaldehyde dimethyl acetal
Synonyms: (2,2-dimethoxyethoxymethyl)benzene

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Benzyloxyacetaldehyde dimethyl acetal
CAS number: 127657-97-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H16O3
Molecular weight: 196.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  苄氧基乙醛二甲基乙缩醛 在 lithium aluminium tetrahydride 、 正丁基锂 、 三氟化硼乙醚 、 三乙胺 、 二异丙胺 、 lithium diisopropyl amide 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 15.0h， 生成 ethyl (E)-4-benzyloxy-2-isocyano-3-butenoate
  参考文献：
  名称：

  (E)-4-烷氧基-2-氨基-3-丁烯酸衍生物的简便合成

  摘要：

  (E)-4-烷氧基-2-甲酰氨基-3-丁烯酸酯已由 3-烷氧基-1-异氰基丙烯分两步制备。该方法基于 3-alkoxy-1-isocyano-1-lithiopropenes 的反应，3-alkoxy-1-isocyano-1-lithiopropenes 可以通过在 -78 °C 的 THF 中用 LDA 处理 3-alkoxy-1-isocyanopropenes 与氯代碳酸烷基酯的反应，得到4-烷氧基-2-异氰基-3-丁烯酸酯。通过在-20 °C 的 Et2O 中用浓 HCl 处理，这些异氰酯很容易转化为相应的甲酰氨基酯。随后，通过用氯碳酸乙酯进行乙氧基羰基化，然后使用六甲基磷酰三胺 (HMPA) 作为共溶剂，用烷基卤化物进行烷基化，将取代基引入 2-位。

  DOI：

  10.1246/bcsj.72.2307
• 作为产物：
  描述：

  2-氯乙醛缩二甲醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 甲苯 、 苯甲醇 作用下， 生成 苄氧基乙醛二甲基乙缩醛
  参考文献：
  名称：

  Heterocyclic Vinyl Ethers. X. Dialkoxy 1,4-Dioxanes and Alkoxy 1,4-Dioxenes¹

  摘要：

  DOI：

  10.1021/ja01628a108
• 作为试剂：
  描述：

  苯甲醇 、 sodium methylate 、 2-氯乙醛缩二甲醇 在 甲醇 、 氯化钠 、 水 、 phase 、 苄氧基乙醛二甲基乙缩醛 、 2-氯乙醛缩二甲醇 作用下， 70.0~135.0 ℃ 、173.32 kPa 条件下， 反应 4.0h， 生成 苄氧基乙醛二甲基乙缩醛
  参考文献：
  名称：

  Process for preparing alkyl- or aryloxyacetaldehydes

  摘要：

  一种制备式1中R为未取代或单取代或多取代的烷基、芳基、杂芳基、烷基芳基、烷基杂芳基或芳基烷基基团或未取代或单取代或多取代的杂环或烷基杂环的烷基或芳氧基乙醛的方法，包括将式R—OM（II）的化合物与式2的化合物反应，其中R如上所定义，M可以是碱金属原子或碱土金属原子，以形成相应的式3的二烷基缩醛，其中R、R1和R2如上所定义，然后进行缩醛断裂以得到所需的式（I）的烷基或芳氧基乙醛。其中，式2中，R1和R2独立地是C1-C6烷基基团或一起是C2-C6-亚烷基基团，X是卤素原子。

  公开号：

  US20010053852A1

文献信息

• Catalytic Asymmetric Epoxidation of Aldehydes. Optimization, Mechanism, and Discovery of Stereoelectronic Control Involving a Combination of Anomeric and Cieplak Effects in Sulfur Ylide Epoxidations with Chiral 1,3-Oxathianes
  作者：Varinder K. Aggarwal、J. Gair Ford、Sílvia Fonquerna、Harry Adams、Ray V. H. Jones、Robin Fieldhouse

  DOI：10.1021/ja9812150

  日期：1998.8.1

  A range of 1,3-oxathianes based on camphorsulfonic acid have been prepared and tested in the catalytic asymmetric epoxidation of carbonyl compounds. It was found that the 1,3-oxathiane derived from acetaldehyde 5b gave the highest yield and enantioselectivity in the epoxidation process. The enantioselectivity was independent of the solvent and metal catalyst used (although yields were dependent on

  已经制备了一系列基于樟脑磺酸的 1,3-氧杂环己烷并在羰基化合物的催化不对称环氧化中进行了测试。发现衍生自乙醛 5b 的 1,3-氧杂环己烷在环氧化过程中具有最高的产率和对映选择性。对映选择性与所使用的溶剂和金属催化剂无关（尽管产率取决于两者）。将最佳条件应用于一系列醛，并观察到良好的对映选择性和非对映选择性。探索了对映选择性的起源，特别是研究了 1,3-氧杂环己烷的氧的作用。因此，制备了基于樟脑磺酸的1,3-氧杂噻吩（衍生自甲醛）的硫和碳类似物（即，1,3-二噻烷和噻烷类似物）。使用这一系列类似物，空间效应被最小化，以便可以研究电子效应。该系列化合物在催化循环中与...
• [EN] DIOXOLANE ANALOGUES OF URIDINE FOR THE TREATMENT OF CANCER<br/>[FR] ANALOGUES DIOXOLANE D'URIDINE POUR LE TRAITEMENT DU CANCER
  申请人：MEDIVIR AB

  公开号：WO2016030335A1

  公开（公告）日：2016-03-03

  The invention provides compounds of formula (I), wherein: R1 is OR11, or NR5R5'; R2 is H or F; R5 is H, C1-C6alkyl, OH, C(=O)R6, O(C=O)R6 or O(C=O)OR6; R5´ is H or C1-C6alkyl; R6 is C1-C6alkyl or C3-C7cycloalkyl; R13 is H, phenyl, pyridyl, benzyl, indolyl or naphthyl wherein the phenyl, pyridyl, benzyl, indolyl and naphthyl is optionally substituted with 1, 2 or 3 R22; and the other variables are as defined in the claims, which are of use in the treatment of cancer, and related aspects.

  这项发明提供了式(I)的化合物，其中：R1为OR11或NR5R5'；R2为H或F；R5为H、C1-C6烷基、OH、C(=O)R6、O(C=O)R6或O(C=O)OR6；R5´为H或C1-C6烷基；R6为C1-C6烷基或C3-C7环烷基；R13为H、苯基、吡啶基、苄基、吲哚基或萘基，其中苯基、吡啶基、苄基、吲哚基和萘基可选择地被1、2或3个R22取代；其他变量如索权中所定义，用于癌症治疗及相关方面。
• Chemoselective (Trans)thioacetalization of Carbonyl Compounds with a Reusable Lewis Acid-Surfactant-Combined Copper Bis(dodecyl sulfate) Catalyst in Water
  作者：Shiue-Shien Weng、Shen-Chun Chang、Tsuan-Hao Chang、Jong-Pyng Chyn、Shu-Wei Lee、Chao-An Lin、Fong-kuang Chen

  DOI：10.1055/s-0029-1218693

  日期：2010.5

  A Lewis acid-surfactant-combined copper bis(dodecyl sulfate) [Cu(DS)2] catalyst served as an efficient and reusable catalyst for the thioacetalization and transthioacetalization of carbonyl compounds and O,O-acetals in water at room temperature. Some of the major advantages of this procedure are high chemoselectivity, ease of operation and purification without any organic solvent, and high yields.

  路易斯酸表面活性剂复合物铜双(十二烷基硫酸) [Cu(DS)2] 催化剂是一种高效且可重复使用的催化剂，在室温下水中催化羰基化合物和O,O-缩醛的硫缩醛化和硫缩醛转移反应。该方法的主要优点包括高化学选择性、操作和纯化简便且无需任何有机溶剂、高产率。
• Supramolecular Catalysis of the oxa‐Pictet–Spengler Reaction with an Endohedrally Functionalized Self‐Assembled Cage Complex
  作者：Courtney Ngai、Colomba M. Sanchez‐Marsetti、W. Hill Harman、Richard J. Hooley

  DOI：10.1002/anie.202009553

  日期：2020.12.21

  An endohedrally functionalized self‐assembled Fe4L6 cage complex can catalyze oxa‐Pictet—Spengler cyclizations of tryptophols and various aldehyde derivatives, showing strong rate accelerations and size‐selectivity. Selective molecular recognition of substrates controls the reactivity, and the cage is capable of binding and activating multiple different species along the multistep reaction pathway

  内膜功能化的自组装Fe 4 L 6笼状复合物可以催化色酚和各种醛衍生物的Oxa-Pictet-Spengler环化反应，显示出较强的速率加速和尺寸选择性。底物的选择性分子识别控制反应性，并且笼子能够沿着多步反应路径结合并激活多个不同的物种。来自单个宿主分子的功能化活性位点，大小选择性反应性和多步激活的组合说明了催化的仿生性质。
• Inter- and Intramolecular Crotyltitanation of Acetals: A Novel and Effective Route to Three- to Five-Membered Vinylcycloalkanes and Bicyclic Fused Compounds
  作者：Nadine Thery、Jan Szymoniak、Claude Moïse

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1483::aid-ejoc1483>3.0.co;2-y

  日期：2000.4

  η3-Crotyltitanocenes react with acetals to produce homoallylic ethers. The intramolecular coupling involving tethered dienyl acetals provides a convenient access to vinylcycloalkanes and bicyclic fused compounds. This new cyclization reaction proceeds with a total regioselectivity in the exo fashion, and with good to excellent diastereoselectivity depending especially on the tether chain length.

  η3-Crotyltitanocenes 与缩醛反应生成均烯丙基醚。涉及系链二烯基缩醛的分子内偶联提供了获得乙烯基环烷烃和双环稠合化合物的便捷途径。这种新的环化反应以外型方式以总区域选择性进行，并且具有良好至极好的非对映选择性，尤其取决于系链长度。