(S)-2-氨甲基-1-M-Cbz-吡咯烷 | 141774-68-7

• 物质功能分类: 有机原料 - 杂环化合物
• 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: (S)-2-氨甲基-1-M-Cbz-吡咯烷
• 中文别名: (S)-2-氨基甲基-1-n-cbz-吡咯烷；(S)-2-氨甲基-1-M-CBZ-吡咯烷
• 英文名称: benzyl (S)-2-(aminomethyl)pyrrolidine-1-carboxylate
• 英文别名: 2-(S)-aminomethyl-pyrrolidine-1-carboxylic acid benzyl ester；(S)-benzyl 2-(aminomethyl)pyrrolidine-1-carboxylate；benzyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylate
• CAS: 141774-68-7
• 化学式: C₁₃H₁₈N₂O₂
• mdl: MFCD03093059
• 分子量: 234.298
• InChiKey: NQGRCKNDDGCZPV-LBPRGKRZSA-N

物化性质

• 沸点：
  370.5±25.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P233,P260,P261,P264,P270,P271,P280,P301+P312,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (S)-1-Cbz-2-(Aminomethyl)pyrrolidine
Synonyms: (S)-Benzyl 2-(aminomethyl)pyrrolidine-1-carboxylate

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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: (S)-1-Cbz-2-(Aminomethyl)pyrrolidine
CAS number: 141774-68-7

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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, 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: C13H18N2O2
Molecular weight: 234.3

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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

反应信息

• 作为反应物：
  描述：

  (S)-2-氨甲基-1-M-Cbz-吡咯烷 在 sodium tetrahydroborate 、 sodium sulfate 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成 (S)-2-((pyridin-2-ylmethylamino)methyl)-1-N-Cbz-pyrrolidine
  参考文献：
  名称：

  Non-heme manganese complexes of C1-symmetric N4 ligands: Synthesis, characterization and asymmetric epoxidations of α,β-enones

  摘要：

  A series of proline-derived C-1-symmetric chiral tetradentate N ligands and their manganese complexes have been synthesized and characterized. Their applications in enantioselective epoxidations of alpha,beta-enones were explored reaching good yields and up to 71% ee at room temperature. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2012.03.034
• 作为产物：
  描述：

  N-苄氧羰基-L-脯氨酸 在 sodium tetrahydroborate 、 迭氮酸 、 偶氮二甲酸二异丙酯 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 17.83h， 生成 (S)-2-氨甲基-1-M-Cbz-吡咯烷
  参考文献：
  名称：

  立体选择性合成含β-氨基酸的（+）-α-P烯的手性吡咯烷衍生物

  摘要：

  摘要 我们报道了几种含有β-氨基酸部分的对映体纯吡咯烷衍生物的合成。这些新型手性化合物是通过将立体定向的氯磺酰基异氰酸酯（CSI）添加到易于获得的天然萜烯（+）-α-pine烯中制备的。使用混合酸酐活化方法将N -Boc保护的β-氨基酸衍生物与各种笨重的胺和氨基酸偶联，然后进行N-脱保护，以良好的产率得到相应的手性氨基酰胺。尽管预期在基于α-pine烯的杂环中存在严重的空间位阻，但氨基酰胺和氨基酯与N -Cbz保护的酰氯的有效偶联（S脯氨酸以高收率提供了相应的吡咯烷二烯pin衍生物。此外，方便的合成Ñ -Cbz-和Ñ -Boc-单保护（小号）-prolinamine报道。 我们报道了几种含有β-氨基酸部分的对映体纯吡咯烷衍生物的合成。这些新型手性化合物是通过将立体定向的氯磺酰基异氰酸酯（CSI）添加到易于获得的天然萜烯（+）-α-pine烯中制备的。使用混合酸酐活化方法将N -Boc保护的

  DOI：

  10.1055/s-0033-1339291

文献信息

• [EN] ORGANOCATALYSTS AND METHODS OF USE IN CHEMICAL SYNTHESIS<br/>[FR] ORGANOCATALYSEURS ET PROCEDES D'UTILISATION DE CES DERNIERS DANS LA SYNTHESE CHIMIQUE
  申请人：STC UNM

  公开号：WO2006007586A1

  公开（公告）日：2006-01-19

  The present invention pertains generally to compositions comprising organocatalysts that facilitate stereo-selective reactions and the method of their synthesis and use. Particularly, the invention relates to metal-free organocatalysts for facilitation of stereo-­selective reactions, and the method of their synthesis and use. These compounds have the structure of the Formulas (I) and (II). Where X is independently selected from CH2, N-Ra, O, S or C=O; Y is CH2, N-Ra, O, S or C=O, with the proviso that at least one of X or Y is CH2, and preferably both of X and Y are CH2; Ra is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 alkyl including a C3-C6 cyclic alkyl group, or an optionally substituted aryl group, preferably an optionally substituted phenyl group; Rb is H, an optionally substituted C1-C12 alkyl, preferably an optionally substituted C1-C6 acyclic or a a C3-C6 cyclic alkyl group, CHO, N(Me)O, CO(S)Ra or the group of Formula (III). Where Rc and Rd are each independently H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C12 alkyl, more preferably a C1-C6 alkyl, and an optionally substituted aryl group, or together Rc and Rd form an optionally substituted carbocyclic or optionally substituted heterocyclic ring; R1 is OH, OR, NR'R', NHC(=O)R, NHSO2R; R2 is H, F, C1, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1­C6 alkyl, an optionally substituted aryl group or a =O group (which establishes a carbonyl group with the carbon to which =O is attached; R3 is H, OH, F, C1, Br, I, Cl, an optionally substituted C1-C20 alkyl, alkenyl or alkynyl ('hydrocarbyl') group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl, such that the carbon to which R3 is attached has an R or S configuration; R is H, an optionally substituted C1-C20 alkyl, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group, R' and R' are each independently H, an optionally substituted C1-C20 alkyl group, preferably an optionally substituted C1-C6 alkyl, or an optionally substituted aryl group; or together R' and R' form an optionally substituted heterocyclic, preferably a 4 to 7 membered optionally substituted heterocyclic group or an optionally substituted heteroaryl ring with the nitrogen to which R' and R' are attached; and wherein said compound is free from a metal catalyst.

  本发明涉及一般包括有机催化剂的组合物，该催化剂促进立体选择性反应以及其合成和使用方法。特别地，本发明涉及无金属有机催化剂以促进立体选择性反应，以及其合成和使用方法。这些化合物具有以下结构的式（I）和（II）。其中X独立地选择自CH2、N-Ra、O、S或C=O；Y为CH2、N-Ra、O、S或C=O，但至少X或Y中的一个为CH2，最好是X和Y都为CH2；Ra为H、可选择地取代的C1-C12烷基，最好是可选择地取代的C1-C6烷基，包括C3-C6环烷基，或可选择地取代的芳基，最好是可选择地取代的苯基；Rb为H、可选择地取代的C1-C12烷基，最好是可选择地取代的C1-C6无环或C3-C6环烷基，CHO、N(Me)O、CO(S)Ra或式（III）的基团。其中Rc和Rd各自独立地为H、F、C1、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C12烷基，更好地是C1-C6烷基，以及可选择地取代的芳基，或者Rc和Rd一起形成可选择地取代的碳环或可选择地取代的杂环；R1为OH、OR、NR'R'、NHC(=O)R、NHSO2R；R2为H、F、C1、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C6烷基，可选择地取代的芳基或=O基团（与=O连接的碳形成羰基基团）；R3为H、OH、F、C1、Br、I、Cl、可选择地取代的C1-C20烷基、烯基或炔基（'烃基'），最好是可选择地取代的C1-C6烷基，或可选择地取代的芳基，使得R3连接的碳具有R或S构型；R为H、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C6烷基，或可选择地取代的芳基，R'和R'各自独立地为H、可选择地取代的C1-C20烷基，最好是可选择地取代的C1-C6烷基，或可选择地取代的芳基；或者R'和R'一起形成可选择地取代的杂环，最好是4到7成员的可选择地取代的杂环基团或与R'和R'连接的氮原子形成可选择地取代的杂芳基环；其中所述化合物不含金属催化剂。
• Enantio- and Diastereoselective Michael Addition Reactions of Unmodified Aldehydes and Ketones with Nitroolefins Catalyzed by a Pyrrolidine Sulfonamide
  作者：Jian Wang、Hao Li、Bihshow Lou、Liansuo Zu、Hua Guo、Wei Wang

  DOI：10.1002/chem.200600115

  日期：2006.5.24

  Chiral (S)-pyrrolidine trifluoromethanesulfonamide has been shown to serve as an effective catalyst for direct Michael addition reactions of aldehydes and ketones with nitroolefins. A wide range of aldehydes and ketones as Michael donors and nitroolefins as acceptors participate in the process, which proceeds with high levels of enantioselectivity (up to 99 % ee) and diastereoselectivity (up to 50:1

  已显示手性（S）-吡咯烷三氟甲磺酰胺可作为醛和酮与硝基烯烃的直接迈克尔加成反应的有效催化剂。作为迈克尔供体的多种醛和酮以及作为受体的硝基烯烃参与了该过程，该过程以高水平的对映选择性（高达99％ee）和非对映选择性（高达50：1 dr）进行。该方法已成功地用于有效的H（3）激动剂Sch 50917的有效合成中。此外，已经开发了一种用于制备（S）-吡咯烷三氟甲烷磺酰胺的实用三步程序。已经通过使用从头算和密度泛函方法研究了由该吡咯烷磺酰胺催化的参与迈克尔加成反应的高水平立体化学控制。已计算出了限速C-C键形成步骤的过渡态结构，该结构对应于关键烯胺中间体的反应构象的表面和表面加成。对这些结构的分析表明，氢键在催化中起重要作用，并且醛在形成2R，3S产物的反应中si-face攻击的能垒比导致2S，3R产物的表面攻击要低。 。相反，在酮的反应中，用于表面添加的能垒比用于硅表面添加的能垒低。在这些迈克尔
• Syntheses of Chiral Ferrocenophanes and Their Application to Asymmetric Catalysis
  作者：Qiying Zhang、Xiuling Cui、Lianmei Chen、Haitao Liu、Yangjie Wu

  DOI：10.1002/ejoc.201402985

  日期：2014.12

  easily synthesized from 1,1′-ferrocenedicarbaldehyde and aliphatic amines in high yields. One of the ferrocenophanes served as a ligand for the copper-catalyzed oxidative coupling of 2-naphthol derivatives to give the products in good yields with up to 92 % ee, and it also efficiently catalyzed the asymmetric Michael addition reaction as an organocatalyst.

  N-取代的 2-氮杂-[3]-二茂铁很容易从 1,1'-二茂铁二甲醛和脂肪胺以高产率合成。其中一种二茂铁作为配体用于铜催化的 2-萘酚衍生物氧化偶联，以高达 92% ee 的良好收率得到产物，并且它还作为有机催化剂有效催化不对称迈克尔加成反应。
• Chiral Zwitterions from Vicinal Diamines: Effective and Recoverable Asymmetric Enamine Catalysts
  作者：Sanzhong Luo、Yupu Qiao、Long Zhang、Jin-Pei Cheng

  DOI：10.1055/s-0030-1259512

  日期：2011.3

  A series of chiral zwitterionic vicinal diamines were designed and synthesized. The zwitterionic catalysts demonstrated good reactivity and enantioselectivity in asymmetric enamine-based transformations and could be readily recycled and reused for four times.

  一系列手性双电离邻二胺被设计和合成。该双电离催化剂在不对称酰胺基转化中表现出良好的反应性和对映选择性，并且可以方便地回收和重复使用四次。
• [EN] SOMATOSTATIN MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DE SOMATOSTATINE ET LEURS UTILISATIONS
  申请人：CRINETICS PHARMACEUTICALS INC

  公开号：WO2017003724A1

  公开（公告）日：2017-01-05

  Described herein are compounds that are somatostatin modulators, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders that would benefit from modulation of somatostatin activity.

  本文描述了一些能够调节生长抑素的化合物，制备这些化合物的方法，包含这些化合物的药物组合物和药物，以及使用这些化合物治疗需要调节生长抑素活性的疾病、症状或障碍的方法。