(9b-Benzenesulfonyl-5-oxo-2,3,5,9b-tetrahydro-1H-pyrrolo[2,1-a]isoindol-1-yl)-acetic acid ethyl ester | 206977-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (9b-Benzenesulfonyl-5-oxo-2,3,5,9b-tetrahydro-1H-pyrrolo[2,1-a]isoindol-1-yl)-acetic acid ethyl ester
• 英文别名: ethyl 2-[9b-(benzenesulfonyl)-5-oxo-2,3-dihydro-1H-pyrrolo[2,1-a]isoindol-1-yl]acetate
• CAS: 206977-16-4
• 化学式: C₂₁H₂₁NO₅S
• 分子量: 399.467
• InChiKey: MBEXCNBVFWGAEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (9b-Benzenesulfonyl-5-oxo-2,3,5,9b-tetrahydro-1H-pyrrolo[2,1-a]isoindol-1-yl)-acetic acid ethyl ester 在 镍 作用下， 以 乙醇 为溶剂， 反应 0.08h， 生成 (5-Oxo-2,3,5,9b-tetrahydro-1H-pyrrolo[2,1-a]isoindol-1-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Alkylation and annulation of 3-(phenylsulfonyl)-2-alkyl-2,3-dihydroisoindol-1-ones

  摘要：

  The hydroxylactams obtained from reduction of N-substituted phthalimides were phenylthiated and oxidized to give 3-(phenylsulfonyl)-2,3-dihydroisoindol-1-ones Deprotonation of the sulfones with sodium hydride followed by treatment with electrophiles gave substitution. Sulfones with suitably-disposed alpha,beta-unsaturated ester groups gave cyclic products from intramolecular Michael addition. Desulfurization of the phenylsulfonyl intermediates was effected in quantitative yield using Raney nickel promoted by ultrasound. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00293-7
• 作为产物：
  描述：

  (E)-ethyl 5-(1,3-dioxoisoindolin-2-yl)pent-2-enoate 在 aluminum amalgam 、 sodium hydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 0.33h， 生成 (9b-Benzenesulfonyl-5-oxo-2,3,5,9b-tetrahydro-1H-pyrrolo[2,1-a]isoindol-1-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Alkylation and annulation of 3-(phenylsulfonyl)-2-alkyl-2,3-dihydroisoindol-1-ones

  摘要：

  The hydroxylactams obtained from reduction of N-substituted phthalimides were phenylthiated and oxidized to give 3-(phenylsulfonyl)-2,3-dihydroisoindol-1-ones Deprotonation of the sulfones with sodium hydride followed by treatment with electrophiles gave substitution. Sulfones with suitably-disposed alpha,beta-unsaturated ester groups gave cyclic products from intramolecular Michael addition. Desulfurization of the phenylsulfonyl intermediates was effected in quantitative yield using Raney nickel promoted by ultrasound. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00293-7

文献信息

• Alkylation and annulation of 3-(phenylsulfonyl)-2-alkyl-2,3-dihydroisoindol-1-ones
  作者：Frederick A. Luzzio、DeAnna Piatt Zacherl

  DOI：10.1016/s0040-4039(98)00293-7

  日期：1998.4

  The hydroxylactams obtained from reduction of N-substituted phthalimides were phenylthiated and oxidized to give 3-(phenylsulfonyl)-2,3-dihydroisoindol-1-ones Deprotonation of the sulfones with sodium hydride followed by treatment with electrophiles gave substitution. Sulfones with suitably-disposed alpha,beta-unsaturated ester groups gave cyclic products from intramolecular Michael addition. Desulfurization of the phenylsulfonyl intermediates was effected in quantitative yield using Raney nickel promoted by ultrasound. (C) 1998 Elsevier Science Ltd. All rights reserved.