3-methyl-2-(phenylthio)butan-1-ol | 34220-15-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-methyl-2-(phenylthio)butan-1-ol
• 英文别名: 3-Methyl-2-phenylsulfanylbutan-1-ol；3-methyl-2-phenylsulfanylbutan-1-ol
• CAS: 34220-15-0
• 化学式: C₁₁H₁₆OS
• 分子量: 196.313
• InChiKey: JVJIIWKWJSMHTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-2-(phenylthio)butan-1-ol 在 L-Selectride 、 sodium hydride 、 二甲基亚砜 、 二异丙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成
  参考文献：
  名称：

  Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation

  摘要：

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.

  DOI：

  10.1021/jo034608c
• 作为产物：
  描述：

  异戊酸乙酯 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.17h， 生成 3-methyl-2-(phenylthio)butan-1-ol
  参考文献：
  名称：

  Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation

  摘要：

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.

  DOI：

  10.1021/jo034608c

文献信息

• Chemoenzymatic Cascades for the Enantioselective Synthesis of β‐Hydroxysulfides Bearing a Stereocentre at the C−O or C−S Bond by Ketoreductases
  作者：Fei Zhao、Kate Lauder、Siyu Liu、James D. Finnigan、Simon B. R. Charnock、Simon J. Charnock、Daniele Castagnolo

  DOI：10.1002/anie.202202363

  日期：2022.8

  Four ketoreductases (KREDs) were identified for the enantioselective synthesis of β-hydroxysulfides. KRED311 and KRED349 catalyse the synthesis of β-hydroxysulfides bearing a stereocentre at the C−O bond with opposite absolute configurations via chemoenzymatic cascades from thiophenols/thiols and α-haloketones/alcohols. KRED253 and KRED384 catalyse the synthesis of β-hydroxysulfides bearing a stereocentre

  鉴定了四种酮还原酶 (KRED) 用于 β-羟基硫化物的对映选择性合成。KRED311 和 KRED349 通过苯硫酚/硫醇和 α-卤代酮/醇的化学酶级联催化合成在 C-O 键处具有立体中心且绝对构型相反的 β-羟基硫化物。KRED253 和 KRED384 通过外消旋 α-硫代醛的动态动力学拆分 (DKR) 催化合成在 C-S 键处具有立体中心并具有相反对映选择性的 β-羟基硫化物。
• 1,2-Migrations in alkyl radicals
  作者：S. N. Lewis、J. J. Miller、S. Winstein

  DOI：10.1021/jo00975a003

  日期：1972.5
• Brownbridge, Peter; Warren, Stuart, Journal of the Chemical Society. Perkin transactions I, 1977, # 20, p. 2272 - 2285
  作者：Brownbridge, Peter、Warren, Stuart

  DOI：——

  日期：——
• Do the Electronic Effects of Sulfur Indeed Control the π-Selectivity of γ-Sulfenyl Enones? An Investigation
  作者：Veejendra K. Yadav、K. Ganesh Babu、Masood Parvez

  DOI：10.1021/jo034608c

  日期：2004.5.1

  The electronic effects of sulfur in gamma-sulfenyl enones are not transmitted to the carbonyl carbon through the pi bond as reported previously. The diastereoselectivity is rather controlled by a combination of several other factors. The steric effects arising from the substituents on the sulfur atom and the gamma-carbon and the bulk of the nucleophile constitute the major control elements.