1-benzyl-7-fluoro-3-hydroxyindolin-2-one | 1439599-01-5

• 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: 1-benzyl-7-fluoro-3-hydroxyindolin-2-one
• 英文别名: 1-benzyl-7-fluoro-3-hydroxy-3H-indol-2-one
• CAS: 1439599-01-5
• 化学式: C₁₅H₁₂FNO₂
• 分子量: 257.264
• InChiKey: OKUGGXXDZDPHAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-7-fluoro-3-hydroxyindolin-2-one 、 天然橡胶 在 十二羰基三钌 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以82%的产率得到1-benzyl-7-fluoro-3-hydroxy-3-(3-methylbut-2-en-1-yl)indolin-2-one
  参考文献：
  名称：

  Regioselective Ruthenium Catalyzed Hydrohydroxyalkylation of Dienes with 3-Hydroxy-2-oxindoles: Prenylation, Geranylation, and Beyond

  摘要：

  The direct conversion of secondary to tertiary alcohols via ruthenium(0) catalyzed C-C coupling of substituted 3-hydroxy-2-oxindoles with various dienes is described. Coupling occurs in a completely regioselective manner in the absence of stoichlometric byproducts.

  DOI：

  10.1021/ol401184k
• 作为产物：
  描述：

  1-benzyl-7-fluoroindoline-2,3-dione 在 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 以54%的产率得到1-benzyl-7-fluoro-3-hydroxyindolin-2-one
  参考文献：
  名称：

  Regioselective Ruthenium Catalyzed Hydrohydroxyalkylation of Dienes with 3-Hydroxy-2-oxindoles: Prenylation, Geranylation, and Beyond

  摘要：

  The direct conversion of secondary to tertiary alcohols via ruthenium(0) catalyzed C-C coupling of substituted 3-hydroxy-2-oxindoles with various dienes is described. Coupling occurs in a completely regioselective manner in the absence of stoichlometric byproducts.

  DOI：

  10.1021/ol401184k

文献信息

• Organocatalytic Asymmetric Mannich Reaction of 3-Hydroxyoxindoles/3-Aminooxindoles with in Situ Generated <i>N</i>-Boc-Protected Aldimines for the Synthesis of Vicinal Oxindole–Diamines/Amino Alcohols
  作者：Jing Shan、Baodong Cui、Yu Wang、Chengli Yang、Xiaojian Zhou、Wenyong Han、Yongzheng Chen

  DOI：10.1021/acs.joc.6b00278

  日期：2016.7.1

  A highly efficient asymmetric Mannich reaction of 3-monosubstituted 3-aminooxindoles/3-hydroxyoxindoles with in situ generated N-Boc-protected aldimines catalyzed by the chiral bifunctional thiourea–tertiary amine catalyst has been developed. Under mild reaction conditions, a series of structurally diverse vicinal oxindole–diamines/amino alcohols were smoothly obtained in moderate to high yields (up

  已经开发了由手性双官能硫脲-叔胺催化剂催化的3-单取代的3-氨基氧吲哚/ 3-羟基氧吲哚与原位生成的N -Boc保护的醛亚胺的高效不对称曼尼希反应。在温和的反应条件下，可以中等至高收率（高达99％）顺利获得一系列结构多样的邻位羟吲哚-二胺/氨基醇，非对映选择性和对映选择性（高达95：5 dr和96％ee） 。手性邻位羟吲哚-二胺/氨基醇向螺环型羟吲哚的多功能转化也证明了该方案的综合应用。
• Ruthenium(0)-Catalyzed C–C Coupling of Alkynes and 3-Hydroxy-2-oxindoles: Direct C–H Vinylation of Alcohols
  作者：Tom Luong、Shujie Chen、Ke Qu、Emma L. McInturff、Michael J. Krische

  DOI：10.1021/acs.orglett.7b00174

  日期：2017.2.17

  Upon exposure to a ruthenium(0) catalyst, N-benzyl-3-hydroxy-2-oxindoles react with diverse alkynes to form products of C–H vinylation with complete control of regioselectivity and olefin geometry. This method contributes to a growing body of catalytic processes that enable direct conversion of lower alcohols to higher alcohols in the absence of stoichiometric organometallic reagents.

  暴露于钌(0)催化剂后，N-苄基-3-羟基-2-羟吲哚与多种炔烃反应形成C-H乙烯基化产物，并完全控制区域选择性和烯烃几何形状。该方法有助于不断发展的催化过程，能够在没有化学计量的有机金属试剂的情况下将低级醇直接转化为高级醇。
• Regioselective Ruthenium Catalyzed Hydrohydroxyalkylation of Dienes with 3-Hydroxy-2-oxindoles: Prenylation, Geranylation, and Beyond
  作者：Te-Yu Chen、Michael J. Krische

  DOI：10.1021/ol401184k

  日期：2013.6.21

  The direct conversion of secondary to tertiary alcohols via ruthenium(0) catalyzed C-C coupling of substituted 3-hydroxy-2-oxindoles with various dienes is described. Coupling occurs in a completely regioselective manner in the absence of stoichlometric byproducts.