tert-butyl N-[2-[[2,5-dioxo-3,4-di(propan-2-yloxy)cyclopent-3-en-1-ylidene]methyl]phenyl]carbamate | 1038778-63-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl N-[2-[[2,5-dioxo-3,4-di(propan-2-yloxy)cyclopent-3-en-1-ylidene]methyl]phenyl]carbamate
• CAS: 1038778-63-0
• 化学式: C₂₃H₂₉NO₆
• 分子量: 415.486
• InChiKey: FQOLPXCSPXRWAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(2-{[1-hydroxy-2,3-bis(1-methylethoxy)-4-oxocyclobut-2-enyl]ethynyl}phenyl)carbamic acid 1,1-dimethylethyl ester	1038778-59-4	C23H29NO6	415.486

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[2-[[2,5-dioxo-3,4-di(propan-2-yloxy)cyclopent-3-en-1-ylidene]methyl]phenyl]carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 144.0h， 以62%的产率得到2,3-bis(1-methylethoxy)cyclopenta[b]quinolin-1-one
  参考文献：
  名称：

  A novel entry to cyclopenta[b]quinolines via thermal ring-expansion of (2-aminophenyl)-ethynyl-substituted squaric acid derivatives

  摘要：

  Substituted cyclopenta[b]quinolin-1-ones were prepared by thermal ring-expansion of substituted N-Boc protected 4-(2-aminophenylethynyl)-4-hydroxy-2-cyclobuten-1-ones forming the corresponding 2-aminophenylmethylidene substituted 4-cyclopentene-1,3-diones. Deprotection of the amine resulted in spontaneous condensation giving cyclopenta[b]quinolin-1-ones. Sodium borohydride reduction of these products produced cyclopenta[b]quinolin-1-ols. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.025
• 作为产物：
  描述：

  (2-{[1-hydroxy-2,3-bis(1-methylethoxy)-4-oxocyclobut-2-enyl]ethynyl}phenyl)carbamic acid 1,1-dimethylethyl ester 反应 0.5h， 以85%的产率得到tert-butyl N-[2-[[2,5-dioxo-3,4-di(propan-2-yloxy)cyclopent-3-en-1-ylidene]methyl]phenyl]carbamate
  参考文献：
  名称：

  A novel entry to cyclopenta[b]quinolines via thermal ring-expansion of (2-aminophenyl)-ethynyl-substituted squaric acid derivatives

  摘要：

  Substituted cyclopenta[b]quinolin-1-ones were prepared by thermal ring-expansion of substituted N-Boc protected 4-(2-aminophenylethynyl)-4-hydroxy-2-cyclobuten-1-ones forming the corresponding 2-aminophenylmethylidene substituted 4-cyclopentene-1,3-diones. Deprotection of the amine resulted in spontaneous condensation giving cyclopenta[b]quinolin-1-ones. Sodium borohydride reduction of these products produced cyclopenta[b]quinolin-1-ols. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.025

文献信息

• A novel entry to cyclopenta[b]quinolines via thermal ring-expansion of (2-aminophenyl)-ethynyl-substituted squaric acid derivatives
  作者：Peter S. Zehr、Reem Kayali、Eduardo Peña-Cabrera、Omar Robles-Resendiz、Alma D. Villanueva-Rendon、Björn C.G. Söderberg

  DOI：10.1016/j.tet.2008.03.025

  日期：2008.5

  Substituted cyclopenta[b]quinolin-1-ones were prepared by thermal ring-expansion of substituted N-Boc protected 4-(2-aminophenylethynyl)-4-hydroxy-2-cyclobuten-1-ones forming the corresponding 2-aminophenylmethylidene substituted 4-cyclopentene-1,3-diones. Deprotection of the amine resulted in spontaneous condensation giving cyclopenta[b]quinolin-1-ones. Sodium borohydride reduction of these products produced cyclopenta[b]quinolin-1-ols. (C) 2008 Elsevier Ltd. All rights reserved.