(R)-3-allyl-5-chloro-3-hydroxy-1-methylindolin-2-one | 1178982-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-3-allyl-5-chloro-3-hydroxy-1-methylindolin-2-one
• 英文别名: (3R)-5-chloro-3-hydroxy-1-methyl-3-prop-2-enylindol-2-one
• CAS: 1178982-22-3
• 化学式: C₁₂H₁₂ClNO₂
• 分子量: 237.686
• InChiKey: ZLIHREYWYOLGJN-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氯-1-甲基-1H-吲哚-2,3-二酮 、 烯丙基三甲基硅烷 在 三甲基氯硅烷 、 sodium hexafluoroantimonate 、 2,6-双[(3aS,8aR)-3a,8a-二氢-8H-indeno[1,2-d]恶唑啉-2-基]吡啶 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 24.08h， 以99%的产率得到(R)-3-allyl-5-chloro-3-hydroxy-1-methylindolin-2-one
  参考文献：
  名称：

  Scandium(III)-Catalyzed Enantioselective Allylation of Isatins Using Allylsilanes

  摘要：

  The scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes is described. A catalyst loading as low as 0.05 mol % Is utilized at room temperature to afford the 3-allyl-3-hydroxy-2-oxindoles in excellent yields and enantioselectivity up to 99% ee, including a demonstration of a gram-scale reaction. The effects of additives and varying silyl groups were explored to demonstrate the scope and application.

  DOI：

  10.1021/ol300496v

文献信息

• From allylic alcohols to chiral tertiary homoallylic alcohol: palladium-catalyzed asymmetric allylation of isatins
  作者：Xiang-Chen Qiao、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1016/j.tetasy.2009.04.012

  日期：2009.6

  A palladium-catalyzed asymmetric allylation of isatins with allylic alcohols as an allyl donor was developed by using chiral spiro phosphoramidite ligands. A variety of chiral tertiary homoallylic alcohols 3-allyl-3-hydroxy-2-oxindoles were prepared directly from allylic alcohols in one step with excellent yields and moderate enantioselectivities. This represents the first catalytic asymmetric allylation

  通过使用手性螺环亚磷酰胺配体，开发了钯催化的靛红与烯丙基醇作为烯丙基供体的不对称烯丙基化反应。一步一步直接从烯丙基醇制备各种手性叔均烯丙基醇3-烯丙基-3-羟基-2-氧吲哚，并具有优异的收率和中等的对映选择性。这代表用烯丙基醇作为烯丙基化剂的酮的第一次催化不对称烯丙基化。
• Scandium(III)-Catalyzed Enantioselective Allylation of Isatins Using Allylsilanes
  作者：Nadine V. Hanhan、Yng C. Tang、Ngon T. Tran、Annaliese K. Franz

  DOI：10.1021/ol300496v

  日期：2012.5.4

  The scandium(III)-catalyzed enantioselective Hosomi-Sakurai allylation of isatins with various substituted allylic silanes is described. A catalyst loading as low as 0.05 mol % Is utilized at room temperature to afford the 3-allyl-3-hydroxy-2-oxindoles in excellent yields and enantioselectivity up to 99% ee, including a demonstration of a gram-scale reaction. The effects of additives and varying silyl groups were explored to demonstrate the scope and application.