2-Ethylsulfanylmethyl-benzoic acid | 79313-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Ethylsulfanylmethyl-benzoic acid
• 英文别名: 2-[(Ethylsulfanyl)methyl]benzoic acid；2-(ethylsulfanylmethyl)benzoic acid
• CAS: 79313-52-3
• 化学式: C₁₀H₁₂O₂S
• mdl: MFCD11575985
• 分子量: 196.27
• InChiKey: RVXITNAXCDFMOI-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C(Solv: ethanol (64-17-5))
• 沸点：
  339.8±25.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Ethylsulfanylmethyl-benzoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 2-(ethylsulfanylmethyl)-N-[2-(1H-indol-3-yl)ethyl]benzamide
  参考文献：
  名称：

  A Triple Cascade Sequence as a Strategy for the Construction of the Erythrinane Skeleton

  摘要：

  alpha-Thiocarbocations generated from Pummerer reactions of several o-imido sulfoxides were intercepted by adjacent carbonyl groups to produce alpha-amido-substituted isobenzofurans as transient intermediates. When an olefinic tether was present, intramolecular Diels-Alder cycloaddition occurred followed by a ring-opening-elimination sequence that produced an N-acyliminium ion. Deprotonation of the iminium ion led to oxindole derivatives in good yields, When the iminium ion contained both a Mocking substituent, such as a carbomethoxy group, as a ell as an activated aromatic pi-tether, the N-acyliminium ion intermediate underwent stereoselective spirocyclization to afford cis-3,4-benzoerythrinane or homoerythrinane derivatives in good yield. The overall triple cascade sequence represents an efficient one-pot approach toward the erythrina skeleton in which the spirocyclic ABC skeleton is assembled in a single operation. The scope and limitations of the triple cascade were explored by varying both the olefinic and nucleophilic tethers. The required sulfoxide precursors for these Pummerer-induced transformations were easily synthesized starting from 2-[(ethylthio)methyl]benzoic acid. The tandem Pummerer/Diels-Alder/N-acyliminium ion cyclization was used for the synthesis of indoloisoquinoline 38. Since compound 38 was converted to 47 which, in turn, was transformed into erysotramidine (2), its preparation represents an extraordinarily facile, formal synthesis of this member of the Erythrina alkaloid family.

  DOI：

  10.1021/jo9716183
• 作为产物：
  描述：

  苯酞 、 乙硫醇钠 以 乙醇 为溶剂， 反应 3.0h， 以90%的产率得到2-Ethylsulfanylmethyl-benzoic acid
  参考文献：
  名称：

  串联Pummerer-Diels-Alder反应序列。一种新型的级联方法，用于制备1-芳基萘木质素。

  摘要：

  由邻苯甲酰基取代的亚砜的Pummerer反应产生的α-硫代碳原子化被相邻的酮基团截获，以生成α-硫代异苯并呋喃作为过渡中间体，随后进行狄尔斯-阿尔德环加成反应并加入亲二烯体。酸催化环加合物的开环，然后进行芳构化，得到芳基萘衍生物。对于炔属二烯亲和物，串联环化-环加成序列提供了四氢萘酮，其是主要环加合物的频哪醇型重排。该方法的多功能性是通过合成taiwanin C和E以及Justicidin E来突出显示的。苯并[1,3]二恶酚-5-基-[6-[（乙基亚硫酰基）甲基]的Pummerer反应产生的α-硫代碳酸盐化反应苯并[1，3]二氧杂-5-基）甲酮被相邻的酮基团拦截，生成α-硫代异苯并呋喃，作为过渡中间体，随后与马来酸二甲酯进行狄尔斯-阿尔德环加成反应。最初形成的Diels-Alder环加合物易于转化为5-苯并[1,3]二恶唑-5-基-8-（乙硫基）萘并[2,3-d] [1,3]二恶唑-6,

  DOI：

  10.1021/jo960295s

文献信息

• Generation and Subsequent Cycloaddition Chemistry of α-Amino Isobenzofurans Formed by Cationic Cyclization
  作者：C. Oliver Kappe、John E. Cochran、Albert Padwa

  DOI：10.1016/0040-4039(95)02013-f

  日期：1995.12

  The α-thiocarbocation generated from the Pummerer reaction of an o-amido substituted sulfoxide is intercepted by the adjacent carbonyl group to produce an α-amino isobenzofuran as a transient intermediate which undergoes a subsequent Diels-Alder cycloaddition with added dienophiles.

  由邻氨基取代的亚砜的Pummerer反应产生的α-硫代碳酸盐化被相邻的羰基拦截，产生α-氨基异苯并呋喃作为过渡中间体，随后进行狄尔斯-阿尔德环加成反应并加入了亲二烯体。
• Studies Dealing with the Cycloaddition/Ring Opening/Elimination Sequence of 2-Amino-Substituted Isobenzofurans
  作者：Albert Padwa、C. Oliver Kappe、John E. Cochran、James P. Snyder

  DOI：10.1021/jo962358c

  日期：1997.5.1

  Pummerer reaction of an o-amido-substituted sulfoxide is intercepted by the adjacent amido carbonyl group to produce a 2-amino-substituted isobenzofuran as a transient intermediate. In the presence of an electron-deficient dienophile, the reactive isobenzofuran undergoes a Diels-Alder cycloaddition followed by ring opening to furnish a vinylogous C-acyliminium ion that readily aromatizes. The one-pot

  由邻氨基取代的亚砜的Pummerer反应产生的α-硫代碳酸盐化被相邻的酰胺羰基截取，从而产生了2-氨基取代的异苯并呋喃作为过渡中间体。在缺电子的亲双烯体的存在下，反应性异苯并呋喃经历Diels-Alder环加成反应，然后开环以提供易于芳构化的乙烯基C-酰基亚胺离子。仅当烯烃系链被酯活化或羰基与2-氨基取代的异苯并呋喃的氮原子相邻时，才会发生单锅分子内级联过程。为了检查胺对酰胺对分子内环加成反应过程的影响，已经对基态和过渡态进行了密度泛函理论（DFT）计算。结果强烈表明，酰胺取代的异苯并呋喃因芳环和含氮侧链之间的空间效应而不稳定。基态酰胺能的增加从而减少了内部环加成反应的活化能，并导致Diels-Alder加合物的速度比相应的胺更快。酰胺系链作为串联过程中分子内环加成的远端促进剂出现，产生具有多个稠环的产物。
• Azole derivatives as apelin receptor agonist
  申请人：Sanford Burnham Prebys Medical Discovery Institute

  公开号：US10626096B2

  公开（公告）日：2020-04-21

  The present invention relates to a novel azole derivative as an apelin receptor agonist and a method for treating cardiovascular disease, diabetic disease, renal disease, hypertension, and arteriosclerosis, etc., using the same. The present invention provides a compound represented by formula (I) or a pharmacologically acceptable salt thereof wherein X1 represents —NH═ or —CH═, X2 represents —CH═ or —N═, R1 and R2 each represent a C1 to C6 alkoxy group or the like, R3 represents a heteroaryl group (the heteroaryl group is optionally substituted by a methyl group or the like) or the like, and R4 represents a C1 to C6 alkylthio group or a C2 to C6 alkenyl group (the C1 to C6 alkylthio group and the C2 to C6 alkenyl group are each optionally substituted by one carboxy group or the like) or the like.

  本发明涉及一种作为芹菜素受体激动剂的新型唑衍生物以及用其治疗心血管疾病、糖尿病疾病、肾脏疾病、高血压和动脉硬化等的方法。本发明提供了由式（I）代表的化合物或其药理上可接受的盐 其中 X1 代表-NH═或-CH═，X2 代表-CH═或-N═，R1 和 R2 各自代表 C1 至 C6 烷氧基或类似物、R3 代表杂芳基（杂芳基可选择被甲基或类似基团取代）或类似基团，R4 代表 C1 至 C6 烷硫基或 C2 至 C6 烯基（C1 至 C6 烷硫基和 C2 至 C6 烯基各自可选择被一个羧基或类似基团取代）或类似基团。
• Stereoselective Synthesis of β-1-O-Acyl Derivatives of Carbohydrates: An Application of the Cesium Effect.
  作者：Horst Kunz、Richard Kullmann、Peter Wernig、Jörg Zimmer

  DOI：10.1016/0040-4039(92)88116-m

  日期：1992.4

  The stereoselective formation of anomerically pure 1-O-acyl derivatives of protected carbohydrates is achieved by reaction of the alpha-glycosyl halogenoses with cesium caboxylates.
• Hard acid and soft nucleophile systems. 5. Ring-opening reaction of lactones to .omega.-alkylthio- or .omega.-arylthio carboxylic acids with aluminum halide and thiol
  作者：Manabu Node、Kiyoharu Nishide、Masahito Ochiai、Kaoru Fuji、Eiichi Fujita

  DOI：10.1021/jo00338a020

  日期：1981.12