ethyl 11-(phenylthio)undecanoate | 123053-76-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ethyl 11-(phenylthio)undecanoate
• 英文别名: Ethyl 11-phenylsulfanylundecanoate
• CAS: 123053-76-9
• 化学式: C₁₉H₃₀O₂S
• 分子量: 322.512
• InChiKey: VSRMOJHBCDSJMH-UHFFFAOYSA-N

物化性质

• 沸点：
  417.3±18.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 11-(phenylthio)undecanoate 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 以72%的产率得到十一酸乙酯
  参考文献：
  名称：

  Desulfurization with nickel and cobalt boride: scope, selectivity, stereochemistry, and deuterium-labeling studies

  摘要：

  A variety of organosulfur compounds containing alkylthio and arylthio groups underwent reductive desulfurization under notably mild conditions when treated with nickel boride, generated in situ from nickel chloride hexahydrate and sodium borohydride in methanol-THF(3:1). Phenyl,chloro, and ester groups are not reduced under these conditions, while iodo, bromo, nitrile, aldehyde, ketone, cyclopropane, and olefinic functions are reduced either completely or partially. Deuterium-labeling studies indicate that the hydrogen that is incorporated into the product originates from both the sodium borohydride and the protic solvent, suggesting the intermediacy of dihydrogen. The epimers 3alpha- and 3beta-(phenylthio)cholestane afforded 3alpha- and 3beta-deuteriocholestane, respectively, demonstrating that the reaction proceeds with retention of configuration. The method may thus be employed for the stereospecific preparation of deuterated products from organosulfur compounds. Arguments are presented in support of a tentative mechanism involving an oxidative addition-reductive elimination sequence via a nickel hydride intermediate.

  DOI：

  10.1021/jo00061a011
• 作为产物：
  描述：

  11-溴十一酸 在 silver perchlorate 、 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 90.0h， 生成 ethyl 11-(phenylthio)undecanoate
  参考文献：
  名称：

  Intramolecular cyclization of (.omega.-carboxyalkyl)sulfonium salts. A novel synthesis of macrocyclic lactones

  摘要：

  DOI：

  10.1021/jo00283a010

文献信息

• Regioselective Alkoxycarbonylation of Allyl Phenyl Ethers Catalyzed by Pd/dppb Under Syngas Conditions
  作者：Manuel Amézquita-Valencia、Howard Alper

  DOI：10.1021/acs.joc.6b00522

  日期：2016.5.6

  A simple and regioselective synthesis of phenoxy esters and phenylthio esters is reported. The products are obtained by selective alkoxycarbonylation catalyzed by Pd2(dba)3, 1,4-bis(diphenylphisphino)butane (dppb), and syngas (CO/H2) in chloroform/alcohol. This methodology affords bifunctional products in good yield with excellent n-selectivity and without the need to use additives.

  报道了苯氧基酯和苯硫基酯的简单且区域选择性的合成。该产品由通过Pd催化的选择性烷氧基羰基而获得2（DBA）3，1,4-双（diphenylphisphino）丁烷（DPPB）的合成气（CO / H，和2）的氯仿/醇。这种方法可提供双收率好的产品，并具有出色的n选择性，并且无需使用添加剂。