2-thioxo-cycloheptanecarboxylic acid ethyl ester | 54928-93-7

• 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
• 英文名称: 2-thioxo-cycloheptanecarboxylic acid ethyl ester
• 英文别名: 1-Cycloheptene-1-carboxylic acid, 2-mercapto-, ethyl ester；ethyl 2-sulfanylcycloheptene-1-carboxylate
• CAS: 54928-93-7
• 化学式: C₁₀H₁₆O₂S
• 分子量: 200.302
• InChiKey: DJUARJDPNNUMHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-thioxo-cycloheptanecarboxylic acid ethyl ester 在 重水 作用下， 以 氘代氯仿 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Determination of tautomeric phenotypes of β-thioxo esters and characterization of the tautomeric enethiolic constituents by means of13C NMR spectroscopy

  摘要：

  AbstractThe 13C NMR spectra of 28 enethiolizable β‐thioxo esters and 6 enethiolizable β‐thioxo thioloesters have been recorded in order to establish the tautomeric phenotypes of these compounds. All compounds investigated are essentially enethiolic. The carbonyl‐conjugated (Z)‐enethiol form is the exclusive or predominant tautomer of open‐chain β‐thioxo esters and thioloesters, thioacylmalonates and medium‐sized 2‐alkoxycarbonylcycloalkanethiones. The carbonyl‐conjugated (E)‐enethiol form is identifiable for open‐chain α‐unsubstituted β‐thioxo esters and thioloesters, and abundant for open‐chain α‐substituted β‐thioxo esters. Non‐conjugated enethiol forms [i.e. (Z)‐ and (E)‐isomeric β,γ‐unsaturated β‐mercapto esters] are abundant tautomeric constituents of ω‐substituted and higher 2‐alkoxycarbonylcycloalkanethiones. The chemical shifts of the carbon atoms directly involved in the tautomeric change have been rationalized in terms of substituent screening contributions. Deuterium isotope effects on the central carbon atoms of selected deuterio‐enethiolic compounds have been measured in order to depict the ester group rotamerism in CO‐conjugated (Z)‐enethiols. The abundance of the CO‐conjugated (E)‐enethiols, as well as the preferred population of the non‐conjugated (Z)‐enethiol form relative to the non‐conjugated (E)‐enethiol form, is rationalized in terms of the occurrence of a no‐bond interaction between the lone‐pair electrons of the enethiolic sulphur atom and the ‘chelating’ methylene hydrogen atoms of cis‐alkyl groups.

  DOI：

  10.1002/mrc.1270220105
• 作为产物：
  描述：

  2-氧代环庚烷甲酸乙酯 在 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 11.59h， 生成 2-thioxo-cycloheptanecarboxylic acid ethyl ester
  参考文献：
  名称：

  一种巯基烯酯类化合物的制备方法

  摘要：

  一种巯基烯酯类化合物的制备方法，本发明属于有机化学合成领域，为解决放大生产风险性高等问题，本发明提供的合成路线为三步反应：(1)将起始物料2‑酮甲酸乙酯类化合物与Tf2O(三氟甲磺酸酐)在碱及溶剂A的作用下，生成三氟甲磺酰基保护的烯醇中间体1；(2)再与硫代试剂发生取代反应得到中间体2；(3)中间体2再在脱保护试剂作用下脱保护得到目标产物3。本发明的有益效果在于：采用本发明制备巯基烯酯类化合物的方法，工艺新颖，避免使用硫化氢等有毒气体，提升工艺的整体安全性与环保性等效果，更适合放大生产，解决产业化难题。

  公开号：

  CN113135848A

文献信息

• 一种巯基烯酯类化合物的制备方法
  申请人：深圳市华先医药科技有限公司

  公开号：CN113135848A

  公开（公告）日：2021-07-20

  一种巯基烯酯类化合物的制备方法，本发明属于有机化学合成领域，为解决放大生产风险性高等问题，本发明提供的合成路线为三步反应：(1)将起始物料2‑酮甲酸乙酯类化合物与Tf2O(三氟甲磺酸酐)在碱及溶剂A的作用下，生成三氟甲磺酰基保护的烯醇中间体1；(2)再与硫代试剂发生取代反应得到中间体2；(3)中间体2再在脱保护试剂作用下脱保护得到目标产物3。本发明的有益效果在于：采用本发明制备巯基烯酯类化合物的方法，工艺新颖，避免使用硫化氢等有毒气体，提升工艺的整体安全性与环保性等效果，更适合放大生产，解决产业化难题。
• Cycloalkene derivatives, process for producing the same, and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US06495604B1

  公开（公告）日：2002-12-17

  The present invention provides a compound represented by the formula: wherein R represents an aliphatic hydrocarbon group optionally having substituents, an aromatic hydrocarbon group optionally having substituents, a heterocyclic group optionally having substituents, a group represented by the formula: OR1 (wherein R1 represents a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents) or a group represented by the formula: wherein R1b represents a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents, R1c is, same with or different from R1b, a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents, R0 represents a hydrogen atom or an aliphatic hydrocarbon group, or R and R0 represents a bond with each other, Ar represents an aromatic hydrocarbon group optionally having substituents, and n is an integer of 1 to 4, or a salt thereof, which is a agent for preventing or treating diseases such as cardiac disease, autoimmune disease, septick shock, etc.

  本发明提供了一种化合物，其表示为以下公式：其中R代表脂肪族烃基，可选地具有取代基；芳香族烃基，可选地具有取代基；杂环基，可选地具有取代基；由公式OR1表示的基团（其中R1代表氢原子或脂肪族烃基，可选地具有取代基）或由公式表示的基团：其中R1b代表氢原子或脂肪族烃基，可选地具有取代基，R1c与R1b相同或不同，代表氢原子或脂肪族烃基，可选地具有取代基，R0代表氢原子或脂肪族烃基，或R和R0相互连接，Ar代表芳香族烃基，可选地具有取代基，n是1到4的整数，或其盐，它是一种用于预防或治疗心脏疾病、自身免疫性疾病、败血性休克等疾病的药剂。
• CYCLOALKENE DERIVATIVES, PROCESS FOR PRODUCING THE SAME, AND USE
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1063228A1

  公开（公告）日：2000-12-27

  Compounds represented by formula (1a) or salts thereof, which are preventives/remedies for heart diseases, autoimmune diseases, inflammatory diseases, septic shock, etc., wherein R represents an optionally substituted aliphatic hydrocarbon group, optionally substituted aromatic hydrocarbon group, optionally substituted heterocyclic group, group represented by OR1 (wherein R1 represents hydrogen or an optionally substituted aliphatic hydrocarbon group), or group represented by formula (A) (wherein R1b band R1c are the same or different and each represents hydrogen or an optionally substituted aliphatic hydrocarbon group); R0 represents hydrogen or an aliphatic hydrocarbon group, or R and R0 in combination represent a bond; Ar represents an optionally substituted aromatic hydrocarbon group; and (B) or (C) where n is an integer of 1 to 4.

  式(1a)代表的化合物或其盐，可预防/治疗心脏病、自身免疫性疾病、炎症性疾病、脓毒性休克等、其中 R 代表任选取代的脂肪族烃基、任选取代的芳香族烃基、任选取代的杂环基、由 OR1 代表的基团（其中 R1 代表氢或任选取代的脂肪族烃基）或由式（A）代表的基团（其中 R1b 带 R1c 相同或不同，且各自代表氢或任选取代的脂肪族烃基）；R0 代表氢或脂族烃基，或 R 和 R0 结合代表键； Ar 代表任选取代的芳族烃基；以及 (B) 或 (C) 其中 n 为 1 至 4 的整数。
• prodrugs containing cycloalkene derivatives
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1524263A1

  公开（公告）日：2005-04-20

  The present invention provides a prodrug of a compound represented by the formula: wherein R represents an aliphatic hydrocarbon group optionally having substituents, an aromatic hydrocarbon group optionally having substituents, a heterocyclic group optionally having substituents, a group represented by the formula: OR1 (wherein R1 represents a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents) or a group represented by the formula: wherein R1b represents a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents, R1c is, same with or different from R1b, a hydrogen atom or an aliphatic hydrocarbon group optionally having substituents, R0 represents a hydrogen atom or an aliphatic hydrocarbon group, or R and R0 represents a bond with each other, Ar represents an aromatic hydrocarbon group optionally having substituents, and n is an integer of 1 to 4, or a salt thereof, which is a agent for preventing or treating diseases such as cardiac disease, autoimmune disease, septick shock, etc..

  本发明提供了一种由式表示的化合物的原药： 其中 R 代表任选具有取代基的脂族烃基、任选具有取代基的芳族烃 基、任选具有取代基的杂环基、由式表示的基团：OR1（其中 R1 代表氢原子或任选具有取代基的脂族烃基）或由式表示的基团： 其中 R1b 代表氢原子或任选具有取代基的脂族烃基；R1c 与 R1b 相同或不同，是氢原子或任选具有取代基的脂族烃基；R0 代表氢原子或脂族烃基；或 R 和 R0 互为键；Ar 代表任选具有取代基的芳香族烃基、 和 n 是 1 至 4 的整数，或其盐，可用于预防或治疗疾病，如心脏病、自身免疫性疾病、败血症休克等。
• US6495604B1
  申请人：——

  公开号：US6495604B1

  公开（公告）日：2002-12-17