11-(phenylthio)-1-undecene | 148773-56-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 11-(phenylthio)-1-undecene
• 英文别名: Undec-10-enylsulfanylbenzene
• CAS: 148773-56-2
• 化学式: C₁₇H₂₆S
• 分子量: 262.459
• InChiKey: GUFWFPQKALLGSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  356.8±11.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11-(phenylthio)-1-undecene 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 以83%的产率得到十一烷
  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：

  10-undecen-1-ol tosylate 、 苯硫酚 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 11-(phenylthio)-1-undecene
  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

文献信息

• A Triple Photoredox/Cobalt/Brønsted Acid Catalysis Enabling Markovnikov Hydroalkoxylation of Unactivated Alkenes
  作者：Masanari Nakagawa、Yuki Matsuki、Kazunori Nagao、Hirohisa Ohmiya

  DOI：10.1021/jacs.2c00527

  日期：2022.5.11

  a triple catalysis consisting of photoredox, cobalt, and Brønsted acid catalysts under visible light irradiation. The triple catalysis realizes three key elementary steps in a single catalytic cycle: (1) Co(III) hydride generation by photochemical reduction of Co(II) followed by protonation, (2) metal hydride hydrogen atom transfer (MHAT) of alkenes by Co(III) hydride, and (3) oxidation of the alkyl

  我们展示了在可见光照射下通过由光氧化还原、钴和布朗斯台德酸催化剂组成的三重催化，使用醇对未活化烯烃进行马尔科夫尼科夫加氢烷氧基化。三重催化在单个催化循环中实现了三个关键的基本步骤：（1）通过光化学还原 Co（II）然后质子化生成 Co（III）氢化物，（2）通过 Co 对烯烃的金属氢化物氢原子转移（MHAT） (III)氢化物，和(3)烷基Co(III)配合物氧化成烷基Co(IV)。三种催化剂对质子和电子的精确控制可以消除传统方法中所需的强酸和外部还原剂/氧化剂。