(R)-4-羟基甲基-2,2-二甲基噁唑啉-3-羧酸叔丁酯 | 108149-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: (R)-4-羟基甲基-2,2-二甲基噁唑啉-3-羧酸叔丁酯
• 中文别名: (R)-3-叔丁氧羰基-2,2-二甲基-4-羟甲基恶唑烷；(S)-(-)-3-叔丁氧羰基-2,2-二甲基恶唑啉-4-甲醇；(R)-N-Boc-2,2-二甲基-4-(羟甲基)噁唑烷；(R)-(-)-3-叔丁氧羰基-2,2-二甲基恶唑啉-4-甲醇
• 英文名称: 4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (R)-4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate；(R)-tert-butyl 4-(hydroxymethyl)-2,2-dimethyloxazolidine-3-carboxylate；(tert-butyl (4R)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate)；(R)-4-hydroxymethyl-2,2-dimethyloxazolidin-3-carboxylic acid 3-t-butyl ester；(R)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester；tert-butyl (4R)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 108149-63-9
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: DWFOEHLGMZJBAA-MRVPVSSYSA-N

物化性质

• 沸点：
  314.1±27.0 °C(Predicted)
• 密度：
  1.075±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境中使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (R)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
Synonyms: (S)-1-Boc-2,2-dimethyl-4-hydroxymethyl-oxazolidine

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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: (R)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS number: 108149-63-9

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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: C11H21NO4
Molecular weight: 231.3

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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：

  (R)-4-羟基甲基-2,2-二甲基噁唑啉-3-羧酸叔丁酯 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4(R)-4-((4-chloro-3-methylphenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  设计，合成和活性的2-氧辛酸和N-油酰基乙醇胺类似物的酸性神经酰胺酶抑制剂。

  摘要：

  本文报道了新型N-酰基乙醇胺的合成及其作为αCDase抑制剂的用途。所述化合物是具有3-羟基-4,5-十六碳烯基尾部被醚或硫醚部分取代的鞘氨醇类似物的2-氧代辛酰胺或油酰胺。看来，在2-氧代己酰胺家族中，鞘氨醇分子的C3-OH基团对于在体外和在培养的细胞中抑制都是必需的。此外，尽管（E）-4双键对于抑制活性不是必需的，但是（E）构型是必需的，因为具有（Z）-4不饱和度的类似物不是抑制性的。在体外，没有一种油酰胺抑制aCDase。相反，除了N-油酰基乙醇胺及其类似物具有S-癸基和S-十六烷基取代基外，所有合成的油酰胺均抑制培养细胞中的aCDase，尽管效能相对较低。我们得出的结论是，新型aCDase抑制剂可从电子缺陷型酰基鞘氨醇碱基的N-酰化反应中演变而来。相反，N-油酰基鞘氨醇主链的化学修饰似乎没有提供获得aCDase抑制剂的适当策略。

  DOI：

  10.1016/j.chemphyslip.2006.07.001
• 作为产物：
  描述：

  Boc-L-丝氨酸甲酯 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (R)-4-羟基甲基-2,2-二甲基噁唑啉-3-羧酸叔丁酯
  参考文献：
  名称：

  脂质体 FRET 测定鉴定神经酰胺转运蛋白 (CERT) 的有效药物样抑制剂

  摘要：

  神经酰胺转移蛋白（CERT）介导神经酰胺从内质网到高尔基体的非囊泡转移，从而催化鞘磷脂生物合成的限速步骤。通常，CERT 配体在繁琐的结合测定或使用放射性标记神经酰胺的非均相转移测定中进行评估。本文提出了一种基于福斯特共振能量转移 (FRET) 的简单且灵敏的 CERT 检测方法。为此，我们混合了供体和受体囊泡，每个囊泡含有不同的荧光神经酰胺种类。通过 CERT 介导的荧光神经酰胺转移，建立了 FRET 系统，尽管组件具有高疏水性，但仍可以在 96 孔板格式中进行读数。对 2000 种化合物库的筛选产生了两种新的有效 CERT 抑制剂。一种被批准用于人类，另一种被批准用于动物。通过定量质谱和共聚焦显微镜对细胞活性的评估表明，神经酰胺运输和鞘磷脂生物合成受到抑制。

  DOI：

  10.1002/chem.202003283

文献信息

• Cyclic Peptide-Polymer Complexes and Their Self-Assembly
  作者：Dominique Bélanger、Xia Tong、Sadia Soumaré、Yves L. Dory、Yue Zhao

  DOI：10.1002/chem.200802337

  日期：2009.4.20

  Pepped up polymers: The synthesis and properties of novel chiral cyclic peptides designed to complex with suitable polymers through hydrogen bonding are described. A substituted cyclic peptide self‐assembles into supramolecular nanotubes and develops noncovalent interactions with poly(vinyl alcohol) (PVA) by means of its carboxyl side chains.

  切碎的聚合物：描述了旨在通过氢键与合适的聚合物络合的新型手性环肽的合成和性质。取代的环肽会自组装成超分子纳米管，并通过其羧基侧链与聚乙烯醇（PVA）发生非共价相互作用。
• 作为细胞坏死阻碍剂的吲哚化合物
  申请人：株式会社LG化学

  公开号：CN105636956B

  公开（公告）日：2019-07-09

  本发明涉及化学式(1)的吲哚化合物、或者其药学容许的盐或异构体，及以含有此作为活性成分作为特征的用于预防或治疗细胞坏死及其关联疾病的组合物及组合物的制造方法。
• Aplyronine A, a potent antitumor macrolide of marine origin, and the congeners aplyronines B and C: isolation, structures, and bioactivities
  作者：Makoto Ojika、Hideo Kigoshi、Yoshifumi Yoshida、Takeshi Ishigaki、Masanori Nisiwaki、Itaru Tsukada、Masayuki Arakawa、Hisao Ekimoto、Kiyoyuki Yamada

  DOI：10.1016/j.tet.2007.02.011

  日期：2007.4

  isolated from the sea hare Aplysia kurodai together with the congeners aplyronines B (3) and C (4). The absolute stereostructure of aplyronine A (2) was determined by the instrumental analysis (mainly NMR and MS) and the enantioselective synthesis of the fragments obtained from chemical degradation of aplyronine A (2). The structures of aplyronines B (3) and C (4) were also elucidated. Cytotoxicity and

  从海兔Aplysia kurodai中分离到了一种有效的抗肿瘤大环内酯-Aplyronine A（2），以及同类的aplyronines B（3）和C（4）。通过仪器分析（主要是NMR和MS）和对苯丙氨酸A（2）的化学降解获得的片段的对映选择性合成，确定了苯丙氨酸A（2）的绝对立体结构。还阐明了鸭绿素B（3）和C（4）的结构。肾上腺素A（2）的细胞毒性和抗肿瘤活性进行了评估。
• Stereoselective Formal Total Synthesis of (-)-Didemniserinolipid B
  作者：Kavirayani Prasad、Vasudeva Gandi

  DOI：10.1055/s-0029-1217976

  日期：2009.10

  A formal total synthesis of (-)-didemniserinolipid B from L-(+)-tartaric acid is presented. Key features of the synthesis include construction of the bicyclic acetal core from bisdimethyl amide of tartaric acid and further elaboration by cross metathesis.

  提出了从 L-(+)-酒石酸正式全合成 (-)-didemniserinolipid B。合成的关键特征包括从酒石酸的双二甲基酰胺构建双环缩醛核，并通过交叉复分解进一步阐述。
• Diastereoselective deprotonative metalation of chiral ferrocene derived acetals and esters using mixed lithium–cadmium and lithium–zinc combinations
  作者：Gandrath Dayaker、Aare Sreeshailam、D. Venkata Ramana、Floris Chevallier、Thierry Roisnel、Shinsuke Komagawa、Ryo Takita、Masanobu Uchiyama、Palakodety Radha Krishna、Florence Mongin

  DOI：10.1016/j.tet.2014.02.010

  日期：2014.3

  derivative in 74% yield with 90% de (SP diastereoisomer) using the base generated from CdCl2 and Li(TMP) (3 equiv), and in 85% yield with 91% de (SP diastereoisomer) through a double asymmetric induction using a chiral lithium–zinc base generated from ZnCl2·TMEDA and lithium (R)-bis(1-phenylethyl)amide (4 equiv). In contrast, using a combination prepared from ZnCl2 and Li(TMP) (4 equiv) with the ferrocene carboxylate

  原位双金属组合，尤其是由MCl 2（TMEDA）（M = Zn，Cd; TMEDA = N，N，N'，N'-四甲基乙二胺）和Li（TMP）（3或4当量，TMP = 2筛选了（2,6,6-四甲基哌啶子基）具有手性基团的非对映选择性去质子化二茂铁的能力。使用由CdCl 2和Li（TMP）（3当量）生成的碱，由双丙酮d-葡萄糖生成的二茂铁羧酸盐以74％的产率提供90％的de（S P非对映异构体）相应的2-碘衍生物。收率91％de（S P非对映异构体）通过使用由ZnCl 2 ·TMEDA和锂（R）-双（1-苯乙基）酰胺（4当量）生成的手性锂锌基双不对称诱导。相比之下，使用由ZnCl 2和Li（TMP）（4当量）制备的组合物与由6-（叔丁氧羰基氨基）-6-脱氧-3- O-甲基-1,2- O-异亚丙基获得的二茂铁羧酸盐-α- d -glucofuranose导致ř P分离之后碘在57％衍生物的产率。在分离的S