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 | 860653-33-4

• 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 (4R)-4-[(S)-[(3S)-1-benzyl-3-(1-benzylindol-3-yl)-2-oxoindol-3-yl]-hydroxymethyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 860653-33-4
• 化学式: C₄₁H₄₃N₃O₅
• 分子量: 657.81
• InChiKey: IGEFJLCKCVRWLG-FLPVOTLVSA-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 甲醇 、 lithium aluminium tetrahydride 、 camphor-10-sulfonic acid 、 N,N-二异丙基乙胺 、 乙酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 54.5h， 生成 [(1S,2R,3aS,8bR)-4-benzyl-8b-(1-benzylindol-3-yl)-1-prop-1-en-2-yloxy-1,2,3,3a-tetrahydropyrrolo[2,3-b]indol-2-yl]methoxy-trimethylsilane
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Gliocladin C

  摘要：

  The first total synthesis of gliocladin C, a fungal-derived marine alkaloid containing a rare trioxopiperazine fragment, is reported. This asymmetric synthesis establishes the absolute configuration of this structurally novel natural product.

  DOI：

  10.1021/ol062801y
• 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 12.25h， 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

• Enantioselective Total Synthesis of (+)-Gliocladin C
  作者：Larry E. Overman、Youseung Shin

  DOI：10.1021/ol062801y

  日期：2007.1.1

  The first total synthesis of gliocladin C, a fungal-derived marine alkaloid containing a rare trioxopiperazine fragment, is reported. This asymmetric synthesis establishes the absolute configuration of this structurally novel natural product.
• 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)