ethyl 3,4-epoxycyclohexanecarboxylate | 75281-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: ethyl 3,4-epoxycyclohexanecarboxylate
• 英文别名: ethyl 7-oxabicyclo<4.1.0>heptane-3-carboxylate；7-oxabicyclo[4.1.0]heptane-3-carboxylic acid ethyl ester；ethyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate；3,4-epoxy-cyclohexanecarboxylic acid ethyl ester；Ethyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate；3,4-Epoxy-cyclohexancarbonsaeure-aethylester
• CAS: 75281-54-8
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: ALEAMASTTOYSRW-UHFFFAOYSA-N

物化性质

• 沸点：
  229.9±23.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3,4-epoxycyclohexanecarboxylate 在 ammonium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 ethyl 3-tert-butoxycarbonylamino-4-hydroxy-cyclohexanecarboxylate
  参考文献：
  名称：

  一种依度沙班中间体的制备方法

  摘要：

  本发明公开了一种高纯度依度沙班中间体(1S，3R，4R)‑3‑叔丁氧羰基氨基‑4‑羟基‑环己烷甲酸的制备方法。以式(Ⅳ)所示3‑氨基‑4‑羟基‑环己烷羧酸酯为原料，经氨基保护基保护后得到式(Ⅴ)所示3‑叔丁氧羰基氨基‑4‑羟基‑环己烷羧酸酯，再经酶催化酯化拆分得到光学纯的式(Ⅶ)所示的(1S，3R，4R)‑3‑叔丁氧羰基氨基‑4‑羟基‑环己烷羧酸酯，最后经氢氧化锂水解得到式(Ⅵ)所示的(1S，3R，4R)‑3‑叔丁氧羰基氨基‑4‑羟基‑环己烷甲酸。本发明的方法具有操作简单、绿色环保、选择性高，成本低等优点，可实现大规模工业生产，便于工业推广应用。

  公开号：

  CN107721866B
• 作为产物：
  描述：

  3-环己烯-1-羧酸乙酯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以50%的产率得到ethyl 3,4-epoxycyclohexanecarboxylate
  参考文献：
  名称：

  A new class of analog of the bifunctional radiosensitizer .alpha.-(1-aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol (RSU 1069): the cycloalkylaziridines

  摘要：

  A series of compounds related to alpha-(1-aziridinylmethyl)-2-nitro-1H-imidazole-1-ethanol (RSU 1069, 1) were synthesized and evaluated as selective hypoxic cell cytotoxic agents and as radiosensitizers. The aziridine moiety was replaced with a number of other potential alkylating groups including cycloalkylaziridines and azetidines. The data indicated that modification of the aziridine of 1 resulted in a substantial decrease in the ability of the compounds to selectively kill hypoxic cells. However, these modifications did not affect the compounds' in vitro radiosensitizing activity since many of the derivatives were as potent as 1. All of the compounds that were evaluated in vivo were less toxic than 1, and several members of this series had significant activity. The best compound was trans-alpha-[[(4-bromotetrahydro-2H-pyran-3-yl)amino]methyl]-2-nitro-1H-imidazole-1-ethanol (18), which, due to its activity and log P value, is a candidate for additional in vivo studies.

  DOI：

  10.1021/jm00112a026

文献信息

• Functional group selectivity in reactions of epoxides with tungsten hexachloride
  作者：Michael E. Jung、Jennifer M. Murphy

  DOI：10.1016/j.tetlet.2007.08.136

  日期：2007.11

  The reactivity of several cyclohexene oxides bearing various functional groups toward the reagent tungsten hexachloride is reported. In general, the conversion of the epoxide to the trans dichloride occurs relatively rapidly. Several groups proved stable—esters, sulfides, sulfones, hindered silyl ethers—while others were unstable—alcohols, unhindered silyl ethers, ketones. The diaxial dichloride is

  报道了几种带有各种官能团的环己烯氧化物对试剂六氯化钨的反应性。通常，环氧化物向反式二氯化物的转化相对较快地发生。几组证明稳定-酯，硫化物，砜，受阻的甲硅烷基醚-其他几组不稳定-醇，不受阻碍的甲硅烷基醚，酮。虽然也可以制备二氯二氯化物，但通常形成二轴二氯化物。
• An Expeditious Route to Fluorinated Rapamycin Analogues by Utilising Mutasynthesis
  作者：Rebecca J. M. Goss、Simon Lanceron、Abhijeet Deb Roy、Simon Sprague、Mohammed Nur-e-Alam、David L. Hughes、Barrie Wilkinson、Steven J. Moss

  DOI：10.1002/cbic.200900723

  日期：2010.3.22

  Rapping it up: A series of fluorinated rapamycin analogues may be readily accessed by using a combined synthetic and biosynthetic approach.

  总结：可以使用合成和生物合成相结合的方法轻松获得一系列氟化雷帕霉素类似物。
• 一种依度沙班中间体的制备方法
  申请人：爱斯特(成都)生物制药股份有限公司

  公开号：CN107721866B

  公开（公告）日：2020-09-04

  本发明公开了一种高纯度依度沙班中间体(1S，3R，4R)‑3‑叔丁氧羰基氨基‑4‑羟基‑环己烷甲酸的制备方法。以式(Ⅳ)所示3‑氨基‑4‑羟基‑环己烷羧酸酯为原料，经氨基保护基保护后得到式(Ⅴ)所示3‑叔丁氧羰基氨基‑4‑羟基‑环己烷羧酸酯，再经酶催化酯化拆分得到光学纯的式(Ⅶ)所示的(1S，3R，4R)‑3‑叔丁氧羰基氨基‑4‑羟基‑环己烷羧酸酯，最后经氢氧化锂水解得到式(Ⅵ)所示的(1S，3R，4R)‑3‑叔丁氧羰基氨基‑4‑羟基‑环己烷甲酸。本发明的方法具有操作简单、绿色环保、选择性高，成本低等优点，可实现大规模工业生产，便于工业推广应用。
• DRUG COMPOSITIONS AND METHODS FOR PREVENTING AND TREATING THROMBOSIS OR EMBOLISM
  申请人：OHTA Toshiharu

  公开号：US20090281074A1

  公开（公告）日：2009-11-12

  Drug compositions containing a substituted diamine compound represented by formula (1): Q 1 -Q 2 -r-N(R 1 )-Q 3 -N(R 2 )  (1) wherein Q 3 represents the following group wherein Q 5 represents an alkylene group having 4 carbon atoms, R 3 represents a hydrogen atom, and R 4 represents a 3-6 membered heterocyclic group which may be substituted; are useful for preventing and/or treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after artificial valve or joint replacement, thrombus formation and reocclusion after angioplasty, systemic inflammatory response syndrome (SIRS), multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing.

  含有以下式子（1）所代表的取代二胺化合物的药物组合物： Q1-Q2-r-N（R1）-Q3-N（R2）  （1） 其中，Q3代表以下基团： 其中，Q5代表具有4个碳原子的烷基基团，R3代表氢原子，R4代表可取代的3-6环杂环基团； 该药物组合物对于预防和/或治疗脑梗死、脑栓塞、心肌梗死、心绞痛、肺梗死、肺栓塞、布尔格病、深静脉血栓形成、弥散性血管内凝血综合征、人工瓣膜或关节置换后的血栓形成、血管成形术后的血栓形成和再闭塞、全身性炎症反应综合征（SIRS）、多器官功能障碍综合征（MODS）、体外循环期间的血栓形成或采血时的血凝。
• METHOD FOR TREATING THROMBOSIS OR EMBOLISM AND RELATED DISEASES
  申请人：Ohta Toshiharu

  公开号：US20100099660A1

  公开（公告）日：2010-04-22

  A method for treating cerebral infarction, cerebral embolism, myocardial infarction, angina pectoris, pulmonary infarction, pulmonary embolism, Buerger's disease, deep venous thrombosis, disseminated intravascular coagulation syndrome, thrombus formation after artificial valve or joint replacement, thrombus formation and reocclusion after angioplasty, multiple organ dysfunction syndrome (MODS), thrombus formation during extracorporeal circulation, or blood clotting upon blood drawing is provided. The method includes administration of an effective amount of a compound represented by formula (1):

  提供了一种治疗脑梗塞、脑栓塞、心肌梗死、心绞痛、肺梗塞、肺栓塞、布尔格病、深静脉血栓形成、弥散性血管内凝血综合征、人工瓣膜或关节置换后的血栓形成、血管成形术后的血栓形成和再闭塞、多器官功能障碍综合征（MODS）、体外循环期间的血栓形成或采血时的血液凝固的方法。该方法包括给予化合物（1）式所代表的有效量。