N-[(2R)-1-羟基-2-丙基]-4-甲基苯磺酰胺 | 786709-32-8

• 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: N-[(2R)-1-羟基-2-丙基]-4-甲基苯磺酰胺
• 中文别名: 苯磺酰胺,N-[(1R)-2-羟基-1-甲基乙基]-4-甲基-
• 英文名称: (R)-2-amino-N-tosyl-1-propanol
• 英文别名: (R)-N-(1-hydroxypropan-2-yl)-4-methylbenzenesulfonamide；N-Tosyl-D-Alaninol；N-[(2R)-1-hydroxypropan-2-yl]-4-methylbenzenesulfonamide
• CAS: 786709-32-8
• 化学式: C₁₀H₁₅NO₃S
• 分子量: 229.3
• InChiKey: GMRUIWLGWXFWAI-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Tosyl-D-Alaninol
Synonyms: (R)-N-(1-Hydroxypropan-2-yl)-4-methylbenzenesulfonamide

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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: N-Tosyl-D-Alaninol
CAS number: 786709-32-8

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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.
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: C10H15NO3S
Molecular weight: 229.3

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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, nitrogen oxides, sulfur oxides.

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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：

  N-[(2R)-1-羟基-2-丙基]-4-甲基苯磺酰胺 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 吖丙啶,2-甲基-1-[(4-甲基苯基)磺酰]-,(2R)-
  参考文献：
  名称：

  Absolute configuration of the polyazamacrolides, macrocyclic polyamines produced by a ladybird beetle

  摘要：

  The absolute configuration of the polyazamacrolides, oligomeric macrocycles from the pupal defensive secretion of Epilachna borealis, was determined by comparison of derivatives of the natural material with enantiomerically pure synthetic samples. Samples of a mixture of three (omega-l)-(2-hydroxyethylamino)alkanoic acids and of the corresponding aza-lactones were synthesized from (R)-alaninol. Gas chromatographic comparison of MTPA-amides of the synthetic aza-lactones with the MTPA-amides of aza-lactones prepared from the natural material established that the polyazamacrolides have the (R)-configuration at all stereogenic centers. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01404-x
• 作为产物：
  描述：

  (1S,3R,6S)-3,6-dihydro-3,6-dimethyl-2-tosyl-1λ4,2-thiazine 1-oxide 在 臭氧 作用下， 以 甲醇 为溶剂， 反应 1.25h， 生成 N-[(2R)-1-羟基-2-丙基]-4-甲基苯磺酰胺
  参考文献：
  名称：

  使用手性双（恶唑啉）-铜（II）和-锌（II）三氟甲磺酸酯的N-亚磺酰基二烯亲和剂的不对称杂Diels-Alder反应

  摘要：

  N的不对称杂Diels-Alder（HDA）反应描述了使用双（恶唑啉）-铜（II）和-锌（II）三氟甲磺酸酯的-亚磺酰基二烯亲和物。已经研究了具有环状和非环状的1，3-二烯的环加成。在大多数情况下，使用化学计量的路易斯酸可获得良好的对映选择性（70-98％ee）和产率（60-85％）。环状二烯以内生加合物为主要产物，而无环二烯则提供顺式加合物。HDA加合物已转化为N保护的α-氨基酸甲酯，氨基醇和均烯丙基胺。提出了一种立体化学模型，该模型解释了四面体金属中心对HDA反应的对面选择性。机理研究揭示了积极的非线性效应，推测是由于反应性较低的杂手性络合物的形成所致。对映选择性的温度依赖性研究表明，在锌催化的反应中存在至少两个选择性反应步骤。用10mol％手性路易斯酸进行的反应收率和选择性差。但是，与TMSOTf（100 mol％）结合使用时，可获得高收率（68-86％）和对映选择性（97-98％ee）。

  DOI：

  10.1021/jo0490245

文献信息

• Neutral Alcohol Nucleophiles for the Substitution of α-Bromo Aryl Acetates and Applications to Asymmetric Synthesis of Morpholine Derivatives
  作者：Wongi Park、Yongtae Kim、Yong Sun Park

  DOI：10.1002/ejoc.201900207

  日期：2019.4.24

  Highly stereoselective C–O bond formation in AgOTf‐catalyzed substitution of α‐bromo aryl acetates with neutral alcohol nucleophiles is developed and applied to the preparation of highly enantioenriched 2‐aryl‐morpholine derivatives.

  在中性醇亲核试剂的AgOTf催化的α-溴代芳基乙酸酯的AgOTf催化取代中，形成了高度立体选择性的C-O键，并将其用于制备高度对映体富集的2-芳基-吗啉衍生物。
• Diastereoselective Synthesis of Substituted Morpholines from <i>N</i>-Tethered Alkenols: Total Synthesis of (±)-Chelonin A
  作者：Madhurjya Borah、Upasana Borthakur、Anil K. Saikia

  DOI：10.1021/acs.joc.6b02260

  日期：2017.2.3

  Intramolecular cyclization of nitrogen tethered alkenols catalyzed by palladium chloride leads to substituted morpholines in good yields. The methodology was used for the total synthesis of (±)-chelonin A.

  氯化钯催化的氮系链烷醇的分子内环化反应可产生高产的吗啉。该方法用于（±）-chelonin A的全合成。
• Zinc-Catalyzed Alkyne–Carbonyl Metathesis of Ynamides with Isatins: Stereoselective Access to Fully Substituted Alkenes
  作者：Chaoqun Ao、Xiaohan Yang、Shikun Jia、Xinfang Xu、Yanqiu Yuan、Dan Zhang、Wenhao Hu

  DOI：10.1021/acs.joc.9b02350

  日期：2019.12.6

  A zinc-catalyzed intermolecular alkyne-carbonyl metathesis reaction of ynamides with isatins followed by an amide to ester conversion has been developed, which produces the indolone derivatives with a fully substituted alkene species in good to high yields. The salient features of this reaction include the following: mild reaction conditions, an inexpensive zinc catalyst, a broad substrate scope, the

  已经开发出锌与酰胺的锌催化的分子间炔烃羰基复分解反应，然后由酰胺转化成酯，从而以良好或高收率生产了具有完全取代的烯烃的吲哚酮衍生物。该反应的显着特征包括：温和的反应条件，廉价的锌催化剂，广泛的底物范围，优异的区域控制和立体选择性，并且适合克规模。
• Rhodium-catalyzed diastereoselective synthesis of highly substituted morpholines from nitrogen-tethered allenols
  作者：A. Ziyaei Halimehjani、B. Breit

  DOI：10.1039/d3cc00151b

  日期：——

  Rhodium-catalyzed intramolecular cyclization of nitrogen-tethered allenols was investigated for the synthesis of functionalized morpholines. By using this strategy, various N-protected 2,5- and 2,6-disubstituted as well as 2,3,5- and 2,5,6-trisubstituted morpholines were obtained via an atom-economic pathway with high to excellent yields, diastereo- and enantioselectivities (up to 99% yield, up to

  研究了铑催化的氮拴联烯醇的分子内环化以合成功能化的吗啉。通过使用该策略，通过原子经济途径获得了各种N保护的 2,5- 和 2,6- 二取代以及 2,3,5- 和 2,5,6- 三取代吗啉，收率高至极佳、非对映选择性和对映选择性（产率高达 99%，高达 >99 : 1 dr 和高达 >99.9 ee）。还研究了合成吗啉在臭氧分解、水合、复分解和环氧化反应中的效用。
• Synthesis of 6- and 7-Membered <i>N</i>-Heterocycles Using α-Phenylvinylsulfonium Salts
  作者：Johnathan V. Matlock、Thomas D. Svejstrup、Pradip Songara、Sarah Overington、Eoghan M. McGarrigle、Varinder K. Aggarwal

  DOI：10.1021/acs.orglett.5b02516

  日期：2015.10.16

  A concise synthesis of stereodefined C-substituted morpholines, piperazines, azepines, and oxazepines in moderate to excellent yields (27% to 75%) is reported by reaction of 1,2- or 1,3-amino alcohol/1,2- or 1,3-diamine with an alpha-phenylvinylsulfonium salt. High levels of regio- and diastereoselectivity (from 2:1 to >20:1) are observed through judicious choice of base (Cs2CO3) and solvent (CH2Cl2). Reactions are performed at ambient temperature and open to air and do not require anhydrous solvent. The deprotection of the N-sulfonamide protecting groups (N-Ts and N-Ns) is also demonstrated. Factors affecting regio- and diastereocontrol are discussed.