(Z,R(S))-2-(1-methylethyl)-1-(4-tolylsulfinyl)-1-hepten-3-one | 1300613-79-9

• 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-(1-methylethyl)-1-(4-tolylsulfinyl)-1-hepten-3-one
• 英文别名: (3Z)-2-methyl-3-[[(R)-(4-methylphenyl)sulfinyl]methylidene]octan-4-one
• CAS: 1300613-79-9
• 化学式: C₁₇H₂₄O₂S
• 分子量: 292.442
• InChiKey: RPRISHQMCRIJRB-VMTBQTDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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-(1-methylethyl)-1-(4-tolylsulfinyl)-1-hepten-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99%的产率得到(Z,3R,R(S))-2-(1-methylethyl)-1-(4-tolylsulfinyl)-1-hepten-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：

  (Z,R(S))-2-(1-methylethyl)-1-(4-tolylsulfinyl)-3-(triethylsilyloxy)-1-heptene 在 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (Z,R(S))-2-(1-methylethyl)-1-(4-tolylsulfinyl)-1-hepten-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。
• Stereochemically Controlled Asymmetric 1,2-Reduction of Enones Mediated by a Chiral Sulfoxide Moiety and a Lanthanum(III) Ion
  作者：Shigeyasu Motohashi、Kouichi Nagase、Toshinori Nakakita、Takeshi Matsuo、Yoshikazu Yoshida、Takashi Kawakubo、Motofumi Miura、Masaharu Toriyama、Mikhail V. Barybin

  DOI：10.1021/jo200373a

  日期：2011.5.20

  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).