(1S,2R)-1'-methyl-2-phenylspiro[cyclopropane-1,3'-indolin]-2'-one | 1416060-81-5

• 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: (1S,2R)-1'-methyl-2-phenylspiro[cyclopropane-1,3'-indolin]-2'-one
• 英文别名: (1S,2R)-1'-methyl-2-phenylspiro[cyclopropane-1,3'-indole]-2'-one
• CAS: 1416060-81-5
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: JLHYITJMRKRTFP-RHSMWYFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1S,2S)-2-phenylcyclopropane-1-carboxylic acid 在 silver orthophosphate 、 草酰氯 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 、 三环己基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 生成 (1S,2R)-1'-methyl-2-phenylspiro[cyclopropane-1,3'-indolin]-2'-one
  参考文献：
  名称：

  Silver-Promoted, Palladium-Catalyzed Direct Arylation of Cyclopropanes: Facile Access to Spiro 3,3′-Cyclopropyl Oxindoles

  摘要：

  The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C H bonds is described. Various spiro 3,3'-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.

  DOI：

  10.1021/ol4003338

文献信息

• Highly enantioselective synthesis of spirocyclopropyloxindoles via a Rh(<scp>ii</scp>)-catalyzed asymmetric cyclopropanation reaction
  作者：Yongjian Chi、Lihua Qiu、Xinfang Xu

  DOI：10.1039/c6ob02160c

  日期：——

  carboxylate complex catalyzed enantioselective cyclopropanation reaction of N-Boc diazooxindoles with olefins, including aryl, alkyl, cyclic, and disubstituted olefins, under mild conditions is described. This reaction provides complementary access to the corresponding chiral spirocyclopropyloxindole products in good to high yields with good to excellent enantioselectivities.

  描述了在温和条件下N- Boc重氮杂吲哚与烯烃，包括芳基，烷基，环状和二取代的烯烃的手性二羧酸（II）羧酸酯络合物催化的对映选择性环丙烷化反应。该反应以良好或高收率和良好或优异的对映选择性提供了互补的途径获得相应的手性螺环丙基丙基吲哚产物。
• Highly stereoselective spirocyclopropanation of various diazooxindoles with olefins catalyzed using Ru(<scp>ii</scp>)-complex
  作者：Masaya Tone、Yoko Nakagawa、Soda Chanthamath、Ikuhide Fujisawa、Naofumi Nakayama、Hitoshi Goto、Kazutaka Shibatomi、Seiji Iwasa

  DOI：10.1039/c8ra09212e

  日期：——

  were efficiently synthesized from diazooxindoles and olefins in the presence of a Ru(II)-Pheox catalyst. Among a series of Ru(II)-Pheox catalysts, Ru(II)-Pheox 6e was determined to be the best catalyst for spirocyclopropanation reactions of diazooxindoles with various olefins in high yields (up to 98%) with high diastereoselectivities (up to trans:cis = >99:1<) and enantioselectivities (up to 99% ee)

  在Ru( II )-Pheox 催化剂存在下，由重氮吲哚和烯烃高效合成了光学活性螺环丙氧吲哚衍生物。在一系列 Ru( II )-Pheox 催化剂中，Ru( II )-Pheox 6e被确定为重氮杂吲哚与各种烯烃以高收率（高达 98%）和高非对映选择性（高达反式）进行螺环丙烷化反应的最佳催化剂: cis = >99:1<) 和对映选择性（高达 99% ee）。此外，作为第一个催化不对称合成，抗 HIV 活性候选物4a和 AMPK 调节剂4c的生物活性化合物很容易分别由相应的重氮吲哚1i和1b以高产率和高对映选择性合成（4a：82% 产率，95% ee，4b：99% 产率，93% ee）。
• A Highly Diastereo- and Enantioselective Hg(II)-Catalyzed Cyclopropanation of Diazooxindoles and Alkenes
  作者：Zhong-Yan Cao、Feng Zhou、Yi-Hua Yu、Jian Zhou

  DOI：10.1021/ol302998m

  日期：2013.1.4

  It is reported for the first time that Hg(II) can catalyze the cyclopropanation of diazo reagents and alkenes, which contributes to the unprecedented highly diastereo- and enantioselective synthesis of spirocyclopropyloxindoles.

  首次报道，Hg（II）可以催化重氮试剂和烯烃的环丙烷化反应，从而促进了螺环丙基氧吲哚的前所未有的高度非对映和对映选择性的合成。
• Silver-Promoted, Palladium-Catalyzed Direct Arylation of Cyclopropanes: Facile Access to Spiro 3,3′-Cyclopropyl Oxindoles
  作者：Carolyn L. Ladd、Daniela Sustac Roman、André B. Charette

  DOI：10.1021/ol4003338

  日期：2013.3.15

  The Pd-catalyzed, Ag(I)-mediated intramolecular direct arylation of cyclopropane C H bonds is described. Various spiro 3,3'-cyclopropyl oxindoles can be obtained in good to excellent yields from easily accessible 2-bromoanilides. The kinetic isotope effect was determined and epimerization studies were conducted, suggesting that the formation of a putative Pd-enolate is not operative and that the reaction proceeds via a C-H arylation pathway.