4-[(1,1'-dibenzyl-2-oxo-1,2-dihydro-1'H-[3,3']biindolyl-3-yl)hydroxymethyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester | 860653-29-8

• 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: 4-[(1,1'-dibenzyl-2-oxo-1,2-dihydro-1'H-[3,3']biindolyl-3-yl)hydroxymethyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-[(R)-[(3R)-1-benzyl-3-(1-benzylindol-3-yl)-2-oxoindol-3-yl]-hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 860653-29-8
• 化学式: C₄₁H₄₃N₃O₅
• 分子量: 657.81
• InChiKey: IGEFJLCKCVRWLG-XRBIJUOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  49
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[(1,1'-dibenzyl-2-oxo-1,2-dihydro-1'H-[3,3']biindolyl-3-yl)hydroxymethyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 在 甲酸 、 camphor-10-sulfonic acid 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 苯 为溶剂， 反应 4.5h， 生成 [4-(1,1'-dibenzyl-2-oxo-1,2-dihydro-1'H-[3,3']biindolyl-3-yl)-2,2-dimethyl[1,3]dioxan-5-yl]carbamic acid 9H-fluoren-9-yl methyl ester
  参考文献：
  名称：

  Asymmetric Construction of Quaternary Carbon Stereocenters:  High Stereoselection in Mukaiyama Aldol Reactions of 2-Siloxyindoles with Chiral Aldehydes

  摘要：

  A new synthesis of enantiopure 3,3-disubstituted oxindoles by stereoselective Mukaiyama aldol reaction of 3-substituted 2-siloxyindoles and chiral, enantiopure aidehydes having nitrogen or oxygen substituents at the a carbon is described. When the C3 substituent of the prochiral nucleophile is aryl or heteroaryl, stereoselectivity is high (10-80:1)

  DOI：

  10.1021/ol051172+
• 作为产物：
  描述：

  1-benzyl-3-(1-benzylindol-3-yl)-3H-indol-2-one 在 2,6-二叔丁基-4-甲基吡啶 、 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.25h， 生成 4-[(1,1'-dibenzyl-2-oxo-1,2-dihydro-1'H-[3,3']biindolyl-3-yl)hydroxymethyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric Construction of Quaternary Carbon Stereocenters:  High Stereoselection in Mukaiyama Aldol Reactions of 2-Siloxyindoles with Chiral Aldehydes

  摘要：

  A new synthesis of enantiopure 3,3-disubstituted oxindoles by stereoselective Mukaiyama aldol reaction of 3-substituted 2-siloxyindoles and chiral, enantiopure aidehydes having nitrogen or oxygen substituents at the a carbon is described. When the C3 substituent of the prochiral nucleophile is aryl or heteroaryl, stereoselectivity is high (10-80:1)

  DOI：

  10.1021/ol051172+

文献信息

• Asymmetric Construction of Quaternary Carbon Stereocenters:  High Stereoselection in Mukaiyama Aldol Reactions of 2-Siloxyindoles with Chiral Aldehydes
  作者：Susanta Adhikari、Sebastien Caille、Martin Hanbauer、Vinh X. Ngo、Larry E. Overman

  DOI：10.1021/ol051172+

  日期：2005.6.1

  A new synthesis of enantiopure 3,3-disubstituted oxindoles by stereoselective Mukaiyama aldol reaction of 3-substituted 2-siloxyindoles and chiral, enantiopure aidehydes having nitrogen or oxygen substituents at the a carbon is described. When the C3 substituent of the prochiral nucleophile is aryl or heteroaryl, stereoselectivity is high (10-80:1)