Boc-L-脯氨酸甲酯 | 59936-29-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: Boc-L-脯氨酸甲酯
• 中文别名: 叔丁氧羰基-L-脯氨酸甲酯；叔丁氧羰基-L-脯氨酸乙酯；N-叔丁氧羰基-L-脯氨酸甲酯；N-BOC-L-脯氨酸甲酯；BOC-PRO-OME
• 英文名称: (S)-N-(tert-butoxycarbonyl)proline methyl ester
• 英文别名: N-(tert-butoxycarbonyl)-L-proline methyl ester；1-(tert-butyl) 2-methyl (S)-pyrrolidine-1,2-dicarboxylate；N-Boc-L-proline methyl ester；N-Boc-proline methyl ester；Boc-L-proline methyl ester；(S)-1-tert-Butyl 2-methyl pyrrolidine-1,2-dicarboxylate；1-O-tert-butyl 2-O-methyl (2S)-pyrrolidine-1,2-dicarboxylate
• CAS: 59936-29-7
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: WVDGSSCWFMSRHN-QMMMGPOBSA-N

物化性质

• 沸点：
  135°C/16mmHg(lit.)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  温度保持在0-10°C之间，并应避免加热。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-L-Pro-OMe
Synonyms:

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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: Boc-L-Pro-OMe
CAS number: 59936-29-7

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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: C11H19NO4
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.

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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

制备方法与用途

Boc-L-脯氨酸甲酯是一种氨基酸类衍生物，可用作医药中间体。

反应信息

• 作为反应物：
  描述：

  Boc-L-脯氨酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以90%的产率得到N-甲基-L-脯氨醇
  参考文献：
  名称：

  Ligand effects in enantioface differentiating 1,4 addition to 1,3 diphenyl-2 propen-1 one

  摘要：

  DOI：

  10.1016/s0040-4039(00)86026-8
• 作为产物：
  描述：

  Boc-L-焦谷氨酸甲酯 在 palladium on activated charcoal 2,6-二甲基吡啶 、 氢气 、 二异丁基氢化铝 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， -78.0 ℃ 、275.79 kPa 条件下， 反应 8.33h， 生成 Boc-L-脯氨酸甲酯
  参考文献：
  名称：

  由N-酰基内酰胺和N-酰基吡咯烷酮合成外消旋和对映体纯的内环氨基甲酸酯的高效快捷方法。

  摘要：

  提出了从N-酰基内酰胺和N-酰基吡咯烷类开始构建内环烯氨基甲酸酯的温和，实用和直接的方案。使用DIBAL-H，SuperHyride或NaBH（4）将内酰胺以良好的优异产率还原为相应的α-羟基氨基甲酸酯（4），然后在受阻硝化碱（如2,6）的存在下，由三氟乙酸酐促进β-消除（脱水） -二甲基吡啶，二异丙基乙胺或三乙胺。该方案的微小变化允许制备几种内环烯氨基甲酸酯（12个实例），总产率良好至优异（56-96％）。已证明该方案适用于多种环大小，与不同的保护基团兼容，并且足够温和以防止易于消旋的立体中心消旋。

  DOI：

  10.1021/jo9903297
• 作为试剂：
  描述：

  5-溴-2,2’-联吡啶 在 正丁基锂 、 Boc-L-脯氨酸甲酯 作用下， 以 四氢呋喃 为溶剂， 生成 2,2'-联吡啶
  参考文献：
  名称：

  新型吡咯烷-联吡啶结构的设计与合成

  摘要：

  摘要 本文公开了设计用于结合吡咯烷和联吡啶的结构，吡咯烷是一种特殊的有机催化剂结构，联吡啶是最广泛使用的金属配体之一。已经建立了针对五种此类化合物的稳健且可扩展的合成路线。这些新结构可用于金属-有机协同催化转化，或用作有机催化剂或金属配体。

  DOI：

  10.1080/00397911.2022.2103433

文献信息

• Manganese-Catalyzed Desaturation of N-Acyl Amines and Ethers
  作者：Gang Li、Patrick A. Kates、Andrew K. Dilger、Peter T. Cheng、William R. Ewing、John T. Groves

  DOI：10.1021/acscatal.9b03457

  日期：2019.10.4

  Enamines and enol ethers are versatile synthons for chemical synthesis. While several methods have been developed to access such molecules, prefunctionalized starting materials are usually required, and direct desaturation methods remain rare. Herein, we report direct desaturation reactions of N-protected cyclic amines and cyclic ethers using a mild I(III) oxidant, PhI(OAc)2, and an electron-deficient

  烯胺和烯醇醚是用于化学合成的通用合成子。尽管已经开发出几种方法来接近这些分子，但是通常需要预官能化的起始材料，并且直接去饱和方法仍然很少。在这里，我们报告了使用温和的I（III）氧化剂PhI（OAc）2和电子不足的五氟苯基卟啉锰Mn（TPFPP）Cl的N-保护的环胺和环醚的直接去饱和反应。该系统显示出各种环状胺和醚的α，β-去饱和的高效率。机理探针表明，去饱和反应是通过最初的α-CH羟基化途径发生的，这可以保护产物免于过氧化。
• One-pot conversion of fluorenylmethyl carbamates into tert-butyl carbamates
  作者：Li Wen-Ren、Jiang Jianjun、Madeleine M. Joullié

  DOI：10.1016/s0040-4039(00)60305-2

  日期：1993.2

  N-Fluorenylmethoxycarbonyl groups may be efficiently converted into N-tert-butoxycarbonyl groups by pottassium flouride/Et3N in the presence of Boc2O

  在Boc 2 O存在下，氟化flour / Et 3 N可将N-氟烯基甲氧羰基有效地转化为N-叔丁氧羰基
• New reagent for the introduction of Boc protecting group to amines: Boc-OASUD
  作者：B. Leela Maheswara Rao、Shaik Nowshuddin、Anjali Jha、Murali K. Divi、M. N. A. Rao

  DOI：10.1080/00397911.2017.1366525

  日期：2017.11.17

  ABSTRACT A new reagent, tert-butyl (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) carbonate (Boc-OASUD) for the preparation of N-Boc-amino acids is described. The Boc-OASUD reacts with amino acids and their esters at room temperature in the presence of a base and gives N-Boc-amino acids and their esters in good yields and purity. Introduction of the Boc group takes place without racemization. The Boc-OASUD

  摘要描述了一种用于制备 N-Boc-氨基酸的新试剂叔丁基 (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) 碳酸酯 (Boc-OASUD)。Boc-OASUD 在室温下在碱存在下与氨基酸及其酯反应，并以良好的产率和纯度得到 N-Boc-氨基酸及其酯。Boc 基团的引入无需外消旋化。Boc-OASUD 是一种固体且更稳定，是二碳酸二叔丁酯的更好替代品，二碳酸二叔丁酯熔点低，由于稳定​​性差，必须在塑料容器中分配，而不是玻璃。图形概要
• Oxidative radical cyclizations of diketopiperazines bearing an amidomalonate unit. Heterointermediate reaction sequences toward the asperparalines and stephacidins
  作者：Tynchtyk Amatov、Martin Gebauer、Radek Pohl、Ivana Cisařová、Ullrich Jahn

  DOI：10.1080/10715762.2016.1223295

  日期：2016.11.1

  A novel approach to the diazabicyclo[2.2.2]octane core of prenylated bridged diketopiperazine alkaloids is described by direct oxidative cyclizations of functionalized diketopiperazines mediated by ferrocenium hexafluorophosphate or the Mn(OAc)3*2H2O/Cu(OTf)2 system. Divergent reaction pathways take place depending on the substitution pattern of the substrates and the oxidation conditions such as temperature

  六氟磷酸铁或Mn（OAc）3 * 2H2O / Cu（OTf）2系统介导的官能化二酮哌嗪的直接氧化环化反应，描述了烯丙基桥联二酮哌嗪生物碱的二氮杂双环[2.2.2]辛烷核心的新方法。根据底物的取代方式和氧化条件（例如温度或持久性自由基TEMPO的存在与否），发生不同的反应途径。对于酯取代的二酮哌嗪，酯基对自由基环化的反应结果和立体化学有重大影响。
• Direct Amidation of Esters by Ball Milling**
  作者：William I. Nicholson、Fabien Barreteau、Jamie A. Leitch、Riley Payne、Ian Priestley、Edouard Godineau、Claudio Battilocchio、Duncan L. Browne

  DOI：10.1002/anie.202106412

  日期：2021.9.27

  The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This

  描述了通过球磨对酯进行直接机械化学酰胺化。操作简单的程序需要一种酯、一种胺和亚化学计量的 KOtBu，并被用于制备一个包含 78 个酰胺结构的大型和多样化的库，效率适中至极好。杂芳族和杂环组分特别表明适合这种机械化学协议。这种直接合成平台已应用于活性药物成分 (API) 和农用化学品的合成以及活性药物的克级合成，所有这些都在没有反应溶剂的情况下进行。