(1S-反式)-2-[(苯甲氧基)甲基]-3-环戊烯-1-醇 | 110567-21-0

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: (1S-反式)-2-[(苯甲氧基)甲基]-3-环戊烯-1-醇
• 中文别名: 恩替卡韦中间体-7；(1S,2r)-2-(苄氧基甲基)-1-羟基-3-环戊烯；(1S-反式)-2-(苯甲氧基)甲基-3-环戊烯-1-醇
• 英文名称: (1S,2R)-2-((benzyloxy)methyl)cyclopent-3-enol
• 英文别名: (1S,2R)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol；(1S,2R)-2-(Benzyloxymethyl)-1-hydroxy-3-cyclopentene；(1S,2R)-2-(phenylmethoxymethyl)cyclopent-3-en-1-ol
• CAS: 110567-21-0
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: WACMQXMZXZTKIV-OLZOCXBDSA-N

物化性质

• 沸点：
  318.9±22.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、DCM、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909499000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H227,H302,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: (1S,2R)-2-[(Benzyloxy)methyl]cyclopent-3-en-1-ol
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: (1S,2R)-2-[(Benzyloxy)methyl]cyclopent-3-en-1-ol
CAS number: 110567-21-0

---

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: C13H16O2
Molecular weight: 204.3

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

---

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

用途
是一种用于治疗乙型肝炎感染的口服抗病毒药物。

应用
恩替卡韦中间体-7 是一种有机合成和医药中间体，可在实验室有机合成和化工医药合成过程中使用。

反应信息

• 作为反应物：
  描述：

  (1S-反式)-2-[(苯甲氧基)甲基]-3-环戊烯-1-醇 在 偶氮二甲酸二异丙酯 、 Hg(II) trifluoroacetate 、 三氯化硼 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 34.0h， 生成 (+)-1-<(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-<(E)-2-bromovinyl>-1H,3H-pyrimidine-2,4-dione
  参考文献：
  名称：

  New Convergent Synthesis of Carbocyclic Nucleoside Analogues

  摘要：

  将描述两种趋同的方法用于合成碳环核苷类似物。这两种方法均以从烷基化环戊二烯中选择性制备的立体化学纯环戊醇8为起点。通过这些方法，已合成出dT、FdU和BVdU的碳环类似物。此外，还将展示一种例子中转化为环Sal-前核苷酸及相应核苷酸的过程。

  DOI：

  10.1055/s-2003-41455
• 作为产物：
  描述：

  苄基氯甲基醚 在 diisopinocampheylborane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.33h， 生成 (1S-反式)-2-[(苯甲氧基)甲基]-3-环戊烯-1-醇
  参考文献：
  名称：

  闭环双还原胺化反应不对称合成多羟基化的N-烷氧基哌啶：异黄酮及其类似物的简便制备

  摘要：

  报道了一种新的多羟基化的N-烷氧基哌啶的从头合成，该合成是基于通过用O-取代的羟胺对环戊烯衍生物进行氧化裂解而得到的1，5-二醛的双环还原胺化。通过切割N-烷氧基哌啶的N-O键可访问异黄花碱。

  DOI：

  10.1021/ol203213f

文献信息

• NO Bond as a Glycosidic-Bond Surrogate: Synthetic Studies Toward Polyhydroxylated<i>N</i>-Alkoxypiperidines
  作者：Gaëlle Malik、Angélique Ferry、Xavier Guinchard、Thierry Cresteil、David Crich

  DOI：10.1002/chem.201202374

  日期：2013.2.4

  isofagomine, 3‐deoxyisofagomine, and numerous other N‐alkoxy analogues. The barrier to inversion in these polyhydroxylated N‐alkoxypiperidine derivatives was found by variable‐temperature NMR methods to be approximately 15 kcal mol−1. With the exception of N‐hydroxyisofagomine itself, none of the compounds prepared showed significant inhibitory activity against sweet almond β‐glucosidase.

  通过将高度官能化的1,5-二醛与各种羟胺进行双环双还原胺化（DRA），合成了一系列新型的多羟基N-烷氧基哌啶。所需的基于糖的二醛是由环戊二烯化钠分七步高效制备的。已经为DRA开发了两步协议。脱保护后，它导致了异黄酮，3-脱氧异氟谷氨酸和许多其他N-烷氧基类似物。通过变温NMR方法发现这些多羟基化的N-烷氧基哌啶衍生物的转化障碍约为15 kcal mol -1。除了N-hydroxyisofagomine本身，所制备的化合物均未显示出对甜杏仁β-葡萄糖苷酶的显着抑制活性。
• [EN] STING MODULATOR COMPOUNDS, AND METHODS OF MAKING AND USING<br/>[FR] COMPOSÉS MODULATEURS DE STING, ET PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：TAKEDA PHARMACEUTICALS CO

  公开号：WO2019092660A1

  公开（公告）日：2019-05-16

  The present disclosure provides STING modulators/agonists, and methods of synthesis and methods for using for the prophylaxis or treatment of cancer and other STING-related diseases. The present disclosure relates to a compound represented by the Formula (I): wherein each symbol is as defined in the description, or a pharmaceutically acceptable salt thereof.

  本公开提供STING调节剂/激动剂，以及合成方法和用于预防或治疗癌症和其他STING相关疾病的方法。本公开涉及由式(I)表示的化合物：其中每个符号如描述中定义，或其药用可接受盐。
• Synthesis of 2′,3′-Modified Carbocyclic L-Nucleoside Analogues
  作者：Sönke Jessel、Chris Meier

  DOI：10.1002/ejoc.201001473

  日期：2011.3

  New divergent approaches to 2',3'-modified carbocyclic L -nucleoside analogues starting from enantiomerically pure (1R,2S)- or (1S,2R)-2-(benzyloxymethyl)cyclopent-3-enol are described. In the key step, stereochemically pure cyclopentanols were condensed with N3-protected thymine through a modified Mitsunobu protocol. Moreover, several routes to different cyclopentanol derivatives, to prepare carbocyclic

  描述了从对映体纯 (1R,2S)-或 (1S,2R)-2-(苄氧基甲基)cyclopent-3-enol 开始的 2',3'-修饰的碳环 L-核苷类似物的新发散方法。在关键步骤中，立体化学纯环戊醇通过改进的 Mitsunobu 协议与 N3 保护的胸腺嘧啶缩合。此外，通过不同的环戊醇衍生物，制备碳环L -2',3'-didehydro-2',3'-dideoxynucleosides (L -d4N), L -2',3'-dideoxynucleosides (L -ddN),和L-核糖核苷被报道。
• Divergent Synthesis and Biological Evaluation of Carbocyclic α-, <i>iso</i>- and 3′-<i>epi</i>-Nucleosides and their Lipophilic Nucleotide Prodrugs
  作者：Chris Meier、Olaf Ludek、Tobias Krämer、Jan Balzarini

  DOI：10.1055/s-2006-926411

  日期：2006.4

  A new divergent approach towards carbocyclic α-, iso- and 3′-epi-nucleosides starting from enantiomerically pure (1S,2R)-2-benzyloxymethylcyclopent-3-enol (5) is described. In the key step, isomeric cyclopentanols were condensed with a N3-protected pyrimidine nucleobase using a modified Mitsunobu protocol. Moreover, the conversion into the cycloSal-pronucleotides and the effect of the orientation of the nucleobase on anti-HIV activity are reported.

  报道了一种从手性纯的(1S,2R)-2-苄氧甲基环戊-3-烯醇(5)出发合成碳环α-、异-和3′-表-核苷的新分岔方法。在关键步骤中，异构环戊醇与N3保护的嘧啶核碱通过改进的Mitsunobu反应进行缩合。此外，还报道了其转化为环硫酸核苷前体的过程以及核碱取向对HIV抑制活性的影响。
• Hydroxymethyl (methylenecyclopentyl) purines and pyrimidines
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US05206244A1

  公开（公告）日：1993-04-27

  Antiviral activity is exhibited by compounds having the formula ##STR1## and its pharmaceutically acceptable salts.

  抗病毒活性由具有以下结构式的化合物及其药用盐展示。