(Z,R(S))-2-methyl-1-(4-tolylsulfinyl)-1-buten-3-one | 1300614-30-5

• 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: (Z,R(S))-2-methyl-1-(4-tolylsulfinyl)-1-buten-3-one
• 英文别名: (Z)-3-methyl-4-[(R)-(4-methylphenyl)sulfinyl]but-3-en-2-one
• CAS: 1300614-30-5
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: PUXUVBOFOSGCNP-WKTRQSJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z,R(S))-2-methyl-1-(4-tolylsulfinyl)-1-buten-3-one 在 lanthanum(III) chloride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 以89%的产率得到(Z,3R,R(S))-2-methyl-1-(4-tolylsulfinyl)-1-buten-3-ol
  参考文献：
  名称：

  Stereochemically Controlled Asymmetric 1,2-Reduction of Enones Mediated by a Chiral Sulfoxide Moiety and a Lanthanum(III) Ion

  摘要：

  Enantiomerically pure (Z)-beta-sulfinyl allylic alcohols of either handedness can be readily prepared from (Z)-beta-sulfinyl enones using NaBH4 or DIBAL reductants in the presence of LaCl3 as a chelating agent. A chiral sulfoxide auxiliary induces the remote 1,2-asymmetric reduction (1,4-induction) to afford various chiral allylic alcohols in high yields with excellent stereoselectivities (up to 100% de).

  DOI：

  10.1021/jo200373a
• 作为产物：
  描述：

  (S(S))-1-(4-tolylsulfinyl)-3-(triethylsilyloxy)-1-butyne 在 copper(l) cyanide 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 4.25h， 生成 (Z,R(S))-2-methyl-1-(4-tolylsulfinyl)-1-buten-3-one
  参考文献：
  名称：

  Stereochemically Controlled Asymmetric 1,2-Reduction of Enones Mediated by a Chiral Sulfoxide Moiety and a Lanthanum(III) Ion

  摘要：

  Enantiomerically pure (Z)-beta-sulfinyl allylic alcohols of either handedness can be readily prepared from (Z)-beta-sulfinyl enones using NaBH4 or DIBAL reductants in the presence of LaCl3 as a chelating agent. A chiral sulfoxide auxiliary induces the remote 1,2-asymmetric reduction (1,4-induction) to afford various chiral allylic alcohols in high yields with excellent stereoselectivities (up to 100% de).

  DOI：

  10.1021/jo200373a

文献信息

• Remote induction of stereoselective 1,2-addition of aryl Grignard reagents to β-sulfinyl enones
  作者：Toshinori Nakakita、Motofumi Miura、Masaharu Toriyama、Shigeyasu Motohashi、Mikhail V. Barybin

  DOI：10.1016/j.tetlet.2013.12.108

  日期：2014.1

  Optically active tert-allylic alcohols constitute important and often challenging targets in organic synthesis. In this work, we employed a β-sulfinyl moiety as a remote chiral auxiliary to effect asymmetric 1,2-addition of aryl Grignard reagents to enones to form a variety of optically active tert-allylic alcohols. The absolute configuration of a representative alcohol product was determined by X-ray

  旋光性叔烯丙基醇是有机合成中重要且通常具有挑战性的目标。在这项工作中，我们使用β-亚磺酰基部分作为远程手性助剂，以实现芳基格氏试剂与烯酮的不对称1,2-加成反应，从而形成多种光学活性的叔烯丙基醇。代表性醇产物的绝对构型通过X射线晶体学测定。
• Stereoselective synthesis of secondary and tertiary propargylic alcohols induced by a chiral sulfoxide auxiliary
  作者：Daijiro Kobayashi、Motofumi Miura、Masaharu Toriyama、Shigeyasu Motohashi

  DOI：10.1016/j.tetlet.2018.11.070

  日期：2019.1

  The synthesis of optically active secondary and tertiary propargylic alcohols was accomplished by addition of lithium acetylide to chiral β-sulfinyl enones. Only a stoichiometric amount of the lithium acetylide was required and various substituents were tolerated. This reaction could be applied to substrates consisting of both ketones and aldehydes in high yields and excellent diastereoselectivities

  光学活性仲和叔炔丙醇的合成是通过向手性β-亚磺酰基烯酮中添加乙炔化锂来完成的。仅需要化学计量的乙炔化锂，并且容许各种取代基。该反应可以高产率和优异的非对映选择性应用于由酮和醛组成的底物。