(R)-3-allyl-3-hydroxy-1-phenylindolin-2-one | 1178982-20-1

• 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-3-hydroxy-1-phenylindolin-2-one
• 英文别名: (3R)-3-hydroxy-1-phenyl-3-prop-2-enylindol-2-one
• CAS: 1178982-20-1
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: XJZAFJHNNSTHRN-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-苯基靛红 、 烯丙基硼酸频哪醇酯 在 C₄₅H₃₁O₂P 、 bismuth(III) acetate 作用下， 以 环己烷 为溶剂， 反应 28.0h， 以44%的产率得到
  参考文献：
  名称：

  Bi（OAc）3 /手性磷酸催化靛红的对映选择性烯丙基化。

  摘要：

  在这里，我们公开了一种在温和条件下通过简单的二元酸Bi（OAc）3 / CPA系统催化的靛红和烯丙基硼酸酯的对映选择性烯丙基化反应来构建手性3-烯丙基-3-羟基羟吲哚的有效方案。通过ent-CPC-1的正式合成证明了该策略的综合效用。

  DOI：

  10.1039/c9cc07944k

文献信息

• Bi(OAc)₃/chiral phosphoric acid catalyzed enantioselective allylation of isatins
  作者：Jie Wang、Qingxia Zhang、Yao Li、Xiangshuai Liu、Xin Li、Jin-Pei Cheng

  DOI：10.1039/c9cc07944k

  日期：——

  Herein, we disclosed an efficient protocol for the construction of chiral 3-allyl-3-hydroxyoxindoles via the enantioselective allylation reaction of isatins and allylboronates catalyzed by a simple binary acid Bi(OAc)3/CPA system under mild conditions. The synthetic utility of this strategy has been demonstrated through the formal synthesis of ent-CPC-1.

  在这里，我们公开了一种在温和条件下通过简单的二元酸Bi（OAc）3 / CPA系统催化的靛红和烯丙基硼酸酯的对映选择性烯丙基化反应来构建手性3-烯丙基-3-羟基羟吲哚的有效方案。通过ent-CPC-1的正式合成证明了该策略的综合效用。
• 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。
• Organocatalyzed Enantioselective Allylation of Isatins by Using a Chiral Amino Alcohol Derived Squaramide as Catalyst
  作者：Debashis Ghosh、Naveen Gupta、Sayed H. R. Abdi、Sekhar Nandi、Noor-ul H. Khan、Rukhsana I. Kureshy、Hari C. Bajaj

  DOI：10.1002/ejoc.201500155

  日期：2015.5

  3,4-dimethoxycyclobut-3-ene-1,2-dione in two steps. A 2.5 mol-% loading of the organocatalyst successfully catalyzed the asymmetric allylation of isatins with allyltributyltin to give the corresponding 3-allyl-3-hydroxyoxindoles in high yields and enantioselectivities (up to 98 % ee).

  以市售的 3,4-二甲氧基环丁-3-烯-1,2-二酮为原料，分两步合成了一系列新型方酸酰胺基有机催化剂。2.5 mol% 的有机催化剂负载量成功地催化了靛红与烯丙基三丁基锡的不对称烯丙基化，以高产率和对映选择性（高达 98% ee）得到相应的 3-烯丙基-3-羟基吲哚。
• 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.
• Zn-Catalyzed enantioselective allylation and allenylation of isatins by virtue of a proline-derived chiral ligand
  作者：Kuiliang Li、Xiang Sun、Shuangshuang Zhao、Tong Li、Zhenggen Zha、Zhiyong Wang

  DOI：10.1039/d1cc06563g

  日期：——

  An asymmetric allylation and allenylation of isatins with facile organoboron reagents was developed under the catalysis of a Lewis acid. A series of optically pure 3-allyl-3-hydroxyoxindoles and 3-allenyl-3-hydroxyoxindoles can be obtained in excellent yields (up to 99% yield) and high enantioselectivities (up to 97% ee). The possible transition state was supported by DFT calculation and the corresponding

  在路易斯酸的催化下，用简单的有机硼试剂开发了靛红的不对称烯丙基化和烯丙基化。一系列光学纯的 3-allyl-3-hydroxyoxindoles 和 3-allenyl-3-hydroxyoxindoles 可以以优异的产率（高达 99% 的产率）和高对映选择性（高达 97% ee）获得。DFT计算支持了可能的过渡态，并提出了相应的机制。建立了这些手性 3-羟基吲哚的克级实验和进一步的功能化。