反式-4-叔丁氧基-L-脯氨酸 | 79775-07-8

• 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: 反式-4-叔丁氧基-L-脯氨酸
• 中文别名: L-4-羟脯氨酸叔丁酯
• 英文名称: (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylic acid
• 英文别名: H-Hyp(tBu)-OH；(2S,4R)-4-[(2-methylpropan-2-yl)oxy]pyrrolidine-2-carboxylic acid
• CAS: 79775-07-8
• 化学式: C₉H₁₇NO₃
• mdl: MFCD00153445
• 分子量: 187.239
• InChiKey: XTQZONYRNXFGCY-RQJHMYQMSA-N

物化性质

• 熔点：
  204-206℃
• 沸点：
  300.5±42.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.888
• 拓扑面积：
  66
• 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：
  P280
• 危险性描述：
  H302,H317
• 储存条件：
  应存放在2-8°C的环境中，避免光照，并保存在惰性气体中。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: H-Hyp(tBu)-OH
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: H-Hyp(tBu)-OH
CAS number: 79775-07-8

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C9H17NO3
Molecular weight: 187.2

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

H-Hyp(tBu)-OH是一种脯氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  反式-4-叔丁氧基-L-脯氨酸 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 12.25h， 生成 (2S,4R)-(4-tert-butoxypyrrolidin-2-yl)methanol
  参考文献：
  名称：

  [EN] AURORA KINASE COMPOUNDS AND METHODS OF THEIR USE
  [FR] COMPOSÉS DE KINASE AURORA ET LEURS MÉTHODES D'UTILISATION

  摘要：

  本文提供了用于治疗由Aurora激酶介导的疾病的吡咯三嗪化合物。还提供了包含这些化合物的药物组合物以及使用这些化合物和组合物的方法。

  公开号：

  WO2011088045A1
• 作为产物：
  描述：

  异丁烯 、 L-羟基脯氨酸 在 对甲苯磺酸 、 sodium hydroxide 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 76.5h， 以73%的产率得到反式-4-叔丁氧基-L-脯氨酸
  参考文献：
  名称：

  Asymmetric α-Amination of Aldehydes and Ketones Catalyzed by tert-Butoxy-L-Proline

  摘要：

  以反式-3-叔丁氧基-L-脯氨酸和反式-4-叔丁氧基-L-脯氨酸为高效催化剂，描述了醛和酮的不对称亲电α-氨基化反应。在 0°C 或室温条件下，催化剂负载量仅为 5 摩尔%，即可获得良好的产率和较高的对映选择性。

  DOI：

  10.2174/157017809788681293
• 作为试剂：
  描述：

  偶氮二甲酸二苄酯 、 丙醛 在 反式-4-叔丁氧基-L-脯氨酸 、 sodium tetrahydroborate 、 乙醇 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以68%的产率得到(R)-dibenzyl 1-(1-hydroxypropan-2-yl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  Asymmetric α-Amination of Aldehydes and Ketones Catalyzed by tert-Butoxy-L-Proline

  摘要：

  以反式-3-叔丁氧基-L-脯氨酸和反式-4-叔丁氧基-L-脯氨酸为高效催化剂，描述了醛和酮的不对称亲电α-氨基化反应。在 0°C 或室温条件下，催化剂负载量仅为 5 摩尔%，即可获得良好的产率和较高的对映选择性。

  DOI：

  10.2174/157017809788681293

文献信息

• Synthesis of New Diketopiperazines, Thiolation to Thiodiketopiperazines, and Examination of Their ROS-Generating Properties
  作者：Sabilla Zhong、Angela E. E. Wandler、Ute Schepers、Martin Nieger、Stefan Bräse

  DOI：10.1002/ejoc.201500900

  日期：2015.11

  A variety of new symmetrical and unsymmetrical diketopiperazines have been prepared from free amino acids by using a previously developed microwave-assisted protocol. This included the successful incorporation of L-pyroglutamic acid as an unusual building block. The diketopiperazines were then thiolated electrophilically to the corresponding bis(methylthio)- and epidithiodiketopiperazines. Initial

  通过使用先前开发的微波辅助方案，从游离氨基酸制备了各种新的对称和不对称二酮哌嗪。这包括成功地将 L-焦谷氨酸作为一种不寻常的构建块。然后将二酮哌嗪通过亲电巯基化为相应的双(甲硫基)-和桥二硫二酮哌嗪。最初的实验显示了在 HeLa 细胞中产生活性氧的有希望的活性。
• Compound And Method
  申请人：University of Bristol

  公开号：US20150158837A1

  公开（公告）日：2015-06-11

  A compound of formula (I): (I) wherein Y is, Z is OR 10 , NR 11 R 11 SR 11 , S(0)R 11 S0 2 R 11 , R 10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO—R 11 , or a protecting group, and R 11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I). wherein Y is

  公式(I)的化合物：(I)其中Y是，Z是OR10，NR11R11SR11，S(0)R11S02R11，R10是H，可选择地取代的烷基，可选择地取代的环烷基，可选择地取代的烯基，可选择地取代的炔基，可选择地取代的芳基，可选择地取代的杂芳基，可选择地取代的杂环烷基，CO—R11，或保护基，而R11可选择地取代的烷基，可选择地取代的环烷基，可选择地取代的烯基，可选择地取代的炔基，可选择地取代的芳基，可选择地取代的杂芳基，可选择地取代的杂环烷基，或者烷氧基；制备公式(I)的化合物的方法；以及利用公式(I)的化合物制备前列腺素或前列腺素类似物的方法。其中Y是
• [EN] COMPOUND AND METHOD<br/>[FR] COMPOSÉ ET PROCÉDÉ
  申请人：UNIV BRISTOL

  公开号：WO2013186550A1

  公开（公告）日：2013-12-19

  A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO-R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I).

  公式（I）的化合物：（I）其中Y是，Z是OR10，NR11R11 SR11，S（0）R11 S02R11，R10是H，可选地取代的烷基，可选地取代的环烷基，可选地取代的烯基，可选地取代的炔基，可选地取代的芳基，可选地取代的杂环芳基，可选地取代的杂环烷基，CO-R11或保护基，R11是可选地取代的烷基，可选地取代的环烷基，可选地取代的烯基，可选地取代的炔基，可选地取代的芳基，可选地取代的杂环芳基，可选地取代的杂环烷基或烷氧基；制备公式（I）的化合物的方法；以及使用公式（I）的化合物制备前列腺素或前列腺素类似物的方法。
• Synthesis and Structure-Activity Relationships of a Series of Penicillin-Derived HIV Proteinase Inhibitors: Heterocyclic Ring Systems Containing P1' and P2' Substituents
  作者：John Kitchin、Richard C. Bethell、Nicholas Cammack、Simon Dolan、Derek N. Evans、Stuart Holman、Duncan S. Holmes、Peter McMeekin、Chi L. Mo

  DOI：10.1021/jm00048a007

  日期：1994.10

  As an extension of our earlier work based upon a single penicillin-derived thiazolidine moiety we have found that the decahydroisoquinoline grouping, also present in Ro 31-8959, is an effective replacement for one of the thiazolidine units in C2 symmetric penicillin-derived dimers. Reaction of racemic epoxide 6 with [3S-[3 alpha, 4a alpha, 8a alpha]]-decahydro-N-(1,1-dimethylethyl)-3- isoquinolinecarboxamide

  作为我们基于单个青霉素衍生的噻唑烷部分的早期工作的扩展，我们发现十氢异喹啉基团（也存在于Ro 31-8959中）可有效替代C2对称青霉素衍生的二聚体中的噻唑烷单元之一。外消旋环氧化合物6与[3S- [3α，4aα，8aα]]-十氢-N-（1，1-二甲基乙基）-3-异喹啉羧酰胺的反应得到非对映异构体34a和34b。确定34a的羟基的立体化学为（S）。衍生自34a和34b的胺与噻唑烷8a的反应分别得到50和51。化合物50是有效的HIV蛋白酶抑制剂（IC50 = 23 nM），在体外具有针对HIV-1的抗病毒活性（EC50 C8166细胞= 50 nM）。但是，狗体内化合物50及其类似物的药代动力学较差，
• Meeting key synthetic challenges in amanitin synthesis with a new cytotoxic analog: 5′-hydroxy-6′-deoxy-amanitin
  作者：Alla Pryyma、Kaveh Matinkhoo、Antonio A. W. L. Wong、David M. Perrin

  DOI：10.1039/d0sc04150e

  日期：——

  Appreciating the need to access synthetic analogs of amanitin, here we report the synthesis of 5′-hydroxy-6′-deoxy-amanitin, a novel, rationally-designed bioactive analog and constitutional isomer of α-amanitin, that is anticipated to be used as a payload for antibody drug conjugates. In completing this synthesis, we meet the challenge of diastereoselective sulfoxidation by presenting two high-yielding

  认识到需要获得鹅膏蕈碱的合成类似物，在此我们报告了 5′-羟基-6′-脱氧鹅膏蕈碱的合成，这是一种新型的、合理设计的生物活性类似物和 α-鹅膏蕈碱的结构异构体，预计将被使用作为抗体药物缀合物的有效负载。在完成该合成过程中，我们通过提出两种高产率和非对映选择性磺化氧化方法来应对非对映选择性磺化氧化的挑战，以提供毒性更大的 ( R )-亚砜。