(E)-tert-butyl 3-(4-chlorobenzylidene)-2-oxoindoline-1-carboxylate | 1279108-50-7

• 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: (E)-tert-butyl 3-(4-chlorobenzylidene)-2-oxoindoline-1-carboxylate
• CAS: 1279108-50-7
• 化学式: C₂₀H₁₈ClNO₃
• 分子量: 355.821
• InChiKey: NRLXCURSOUPMAO-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,3-丁二烯酸乙酯 、 (E)-tert-butyl 3-(4-chlorobenzylidene)-2-oxoindoline-1-carboxylate 在 β-isocupreidine 作用下， 以 氯仿 为溶剂， 反应 192.0h， 以94%的产率得到(R,E)-tert-butyl 4-(4-chlorophenyl)-2-(2-ethoxy-2-oxoethylidene)-3,4-dihydropyrano[2,3-b]indole-9(2H)-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Dihydropyran-Fused Indoles through [4+2] Cycloaddition between Allenoates and 3-Olefinic Oxindoles

  摘要：

  A highly enantioselective [4+2] annulation with respect to allenoates and 3-olefinic oxindoles catalyzed by Lewis base was reported, which proved to be an efficient way to synthesize chiral dihydropyran-fused indoles. The cycloaddition products were generally obtained in high yields (up to 98%) with very good enantioselectivities (up to 94% enantiomeric excess).

  DOI：

  10.1021/acs.joc.5b00212
• 作为产物：
  描述：

  4-氯苯甲醛 在 哌啶 、 4-二甲氨基吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (E)-tert-butyl 3-(4-chlorobenzylidene)-2-oxoindoline-1-carboxylate
  参考文献：
  名称：

  腈亚胺的不对称催化1,3-偶极环加成反应合成手性螺-吡唑啉-辛醇

  摘要：

  新型的N，N'-二氧化物配体的手性Mg（ClO 4）2配合物催化了腈亚胺与3-烯基-氧吲哚的新的1,3-偶极环加成反应。到目前为止，该反应是螺-吡唑啉-羟吲哚衍生物的唯一催化合成。探索了多种底物以获得良好的产率（高达98％）和优异的对映选择性（高达99％）。这种环加成反应扩大了2-吡唑啉亚基结构中1，3-偶极炔丙基阴离子的范围。

  DOI：

  10.1021/ol303097j

文献信息

• Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole
  作者：Estelle Silm、Ivar Järving、Tõnis Kanger

  DOI：10.3762/bjoc.18.18

  日期：——

  An asymmetric Michael reaction between cyclopentane-1,2-dione and alkylidene oxindole was studied in the presence of a multifunctional squaramide catalyst. Michael adducts were obtained in high enantioselectivities and in moderate diastereoselectivities.

  在多功能方酰胺催化剂存在下，研究了 cyclopentane-1,2-dione 和亚烷基羟吲哚之间的不对称 Michael 反应。迈克尔加合物以高对映选择性和中等非对映选择性获得。
• Highly enantio- and diastereoselective construction of spirocyclic oxindoles via a palladium-catalyzed decarboxylative asymmetric [4 + 2] annulation strategy
  作者：Pengyuan You、Minjie Liu、Ke Zhang、Fan Yang、Zequn Tan、Fener Chen

  DOI：10.1039/d4ob00518j

  日期：——

  A palladium-catalyzed decarboxylative asymmetric [4 + 2] annulation of methyleneindolinones with a zwitterionic oxo-1,4-dipole intermediate was successfully developed to access spirocyclic oxindoles bearing two vicinal stereocenters in good yields with high diastereoselectivities and enantioselectivities. This strategy features a broad substrate scope (28 examples), allowing for efficient scale-up

  成功开发了一种钯催化的亚甲基二氢吲哚酮与两性离子氧代-1,4-偶极中间体的脱羧不对称[4 + 2]成环反应，以良好的收率获得具有两个邻位立构中心的螺环羟吲哚，并具有高非对映选择性和对映选择性。该策略具有广泛的底物范围（28 个示例），可实现高效的放大。对产品进行了进一步的选择性转化和初步的机理研究。
• Construction of Pyrrolidinyl Spirooxindoles via a 1,3-Dipolar Cycloaddition Reaction of (<i>E</i>)-<i>N</i>-Boc-3-Alkylidene-Indolin-2(3<i>H</i>)ones with Azomethine Ylides
  作者：Zhang-Biao Yu、Xiong-Li Liu、Bo-Wen Pan、Bin Chen、Ying Zhou、Hua-Lin Wang

  DOI：10.1080/00397911.2013.820834

  日期：2014.2.16

  A mild and efficient method for the construction of pyrrolidinyl spirooxindoles via a 1,3-dipolar cycloaddition reaction of (E)-N-Boc-3-alkylidene-indolin-2(3H)ones with azomethine ylides has been established. The presence of an N-Boc group in the indolin-2(3H)ones obviously increased the activity and stereoselectivity of the reaction, affording the desired pyrrolidinyl spirooxindoles 4 with up to 85% yield and up to >99/1 dr value. Furthermore, the antibacterial activity of these compounds against Staphylococcus aureus (ATCC-25825) has been tested at minimum concentration, and some of them exhibit moderate antibacterial activity. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]