6-Phenylsulfanyl-hexan-2-one | 172419-22-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-Phenylsulfanyl-hexan-2-one
• 英文别名: 6-(Phenylthio)-2-hexanone；6-phenylsulfanylhexan-2-one
• CAS: 172419-22-6
• 化学式: C₁₂H₁₆OS
• 分子量: 208.324
• InChiKey: SPSNHEYYGXJWQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Phenylsulfanyl-hexan-2-one 在 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醇 为溶剂， 反应 9.0h， 生成 6-methyl-2-(phenylthio)tetrahydropyran
  参考文献：
  名称：

  Applications of highly enantioenriched alcohols bearing a phenylthio group in the preparation of ring compounds. The two-pot synthesis of an enantiopure spiroacetal pheromone bearing three chiral centers

  摘要：

  The new chiron (S)-6-phenylthio-2-hexanol (3) was prepared in high enantiomeric excess by baker's yeast reduction of the corresponding ketone. Enantioenriched alcohols 1, 2 and 3, prepared previously by a similar procedure, or their racemic counterparts, were transformed into ring closed compounds 5-methyl-2-(phenylthio)tetrahydrofuran (9), 6-methyl-2-(phenylthio)tetrahydropyran (10), 2-methyl-1-phenylsulfonyl cyclopropane (14), cyclobutane (15), cyclopentane (16), and a bee pheromone, (2S,6R,8S)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (20). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00635-2
• 作为产物：
  描述：

  6-phenylthio-2-hexanol 在 C₄₄H₆₆O₈P₄Pd₂ 、 丁烯酮 作用下， 以 水 、 甲苯 为溶剂， 反应 16.0h， 以83%的产率得到6-Phenylsulfanyl-hexan-2-one
  参考文献：
  名称：

  次膦氧化物作为多配位的配体在醇的化学选择性钯催化氧化中进行。

  摘要：

  通过吸氢方法，仲膦氧化物O = PHR 2（SPOs）被鉴定为化学选择的Pd催化醇氧化的多态预配体。发现SPO通过产生推定的活性H-Pd物种来促进氢的吸收步骤以及氢向迈克尔受体的转移。该催化体系在中性条件下运行，并被证明与底物中的各种亲电子和亲核官能团以及对水和空气敏感的官能团兼容。

  DOI：

  10.1002/cctc.201601261

文献信息

• Iron(<scp>III</scp>) mediated transformations of cyclopropyltrimethylsilyl ethers. Part 1. Free radical tandem ring expansion–cyclisation reactions for the rapid construction of [n.3.0] bicyclic ring systems
  作者：Kevin I. Booker-Milburn、David F. Thompson

  DOI：10.1039/p19950002315

  日期：——

  trimethylsilyl ethers with anhydrous ferric chloride in dry dimethylformamide leads to diastereoisomerically pure [n.3.0] bicyclic chloro ketones by a novel tandem ring expansion–cyclisation sequence. The reaction is thought to proceed by a mechanism involving the intermediacy of a cyclopropyl alkoxy radical.

  在干燥的二甲基甲酰胺中用无水氯化铁处理许多[ n .1.0]环丙基三甲基甲硅烷基醚会导致新的串联环扩环序列，从而形成非对映异构纯的[ n .3.0]双环氯酮。该反应被认为是通过涉及环丙基烷氧基的中间体的机理来进行的。
• cyclo-SEM: A new carbonyl protecting group
  作者：Bruce H Lipshutz、Paul Mollard、Craig Lindsley、Virginia Chang

  DOI：10.1016/s0040-4039(97)00239-6

  日期：1997.3

  Conversion of aldehydes and ketones to 1,3-dioxanes with 2-trimethylsilyl-1,3-propanediol affords carbonyl-protected products, ultimately susceptible to unmasking with LiBF4 in THF. (C) 1997 Elsevier Science Ltd.
• US7375145B2
  申请人：——

  公开号：US7375145B2

  公开（公告）日：2008-05-20
• Secondary Phosphine Oxides as Multitalented Preligands En Route to the Chemoselective Palladium-Catalyzed Oxidation of Alcohols
  作者：Alexandre Vasseur、Romain Membrat、David Gatineau、Alphonse Tenaglia、Didier Nuel、Laurent Giordano

  DOI：10.1002/cctc.201601261

  日期：2017.3.8

  Secondary phosphine oxides O=PHR2 (SPOs) were identified as multitalented preligands for the chemoselective Pd‐catalyzed oxidation of alcohols by a hydrogen‐abstracting methodology. SPOs were found to promote the hydrogen‐abstraction step as well as hydrogen transfer to a Michael acceptor by generating a putative active H−Pd species. The catalytic system operates under neutral conditions and was proven

  通过吸氢方法，仲膦氧化物O = PHR 2（SPOs）被鉴定为化学选择的Pd催化醇氧化的多态预配体。发现SPO通过产生推定的活性H-Pd物种来促进氢的吸收步骤以及氢向迈克尔受体的转移。该催化体系在中性条件下运行，并被证明与底物中的各种亲电子和亲核官能团以及对水和空气敏感的官能团兼容。
• Applications of highly enantioenriched alcohols bearing a phenylthio group in the preparation of ring compounds. The two-pot synthesis of an enantiopure spiroacetal pheromone bearing three chiral centers
  作者：Theodore Cohen、Shaojing Tong

  DOI：10.1016/s0040-4020(97)00635-2

  日期：1997.7

  The new chiron (S)-6-phenylthio-2-hexanol (3) was prepared in high enantiomeric excess by baker's yeast reduction of the corresponding ketone. Enantioenriched alcohols 1, 2 and 3, prepared previously by a similar procedure, or their racemic counterparts, were transformed into ring closed compounds 5-methyl-2-(phenylthio)tetrahydrofuran (9), 6-methyl-2-(phenylthio)tetrahydropyran (10), 2-methyl-1-phenylsulfonyl cyclopropane (14), cyclobutane (15), cyclopentane (16), and a bee pheromone, (2S,6R,8S)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (20). (C) 1997 Elsevier Science Ltd.