ethyl 2-acetamido-5,6-bis(hydroxymethyl)indan-2-carboxylate | 191215-39-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-acetamido-5,6-bis(hydroxymethyl)indan-2-carboxylate
• 英文别名: Ethyl 2-acetamido-5,6-bis(hydroxymethyl)-1,3-dihydroindene-2-carboxylate
• CAS: 191215-39-1
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: CRPQLYLMKJULDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetamido-5,6-bis(hydroxymethyl)indan-2-carboxylate 在 三溴化磷 作用下， 以 苯 为溶剂， 以81%的产率得到2-acetylamino-5,6-bis(bromomethyl)indane-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Diels-Alder方法通过磺胺中间体合成高度官能化的苯并环化的茚满基α-氨基酸衍生物

  摘要：

  各种高官能度的苯并环化的茚满基的α-氨基酸（AAA）衍生物的合成是通过[4 + 2]环加成策略，使用含有AAA部分的磺化衍生物作为反应性二烯组分进行的。通过采用这种策略，报道了一种新的基于α，α-二烷基化的基于茚满的茚满的C 60富勒烯，其包含受约束的AAA单元。

  DOI：

  10.1016/j.tetlet.2004.02.060
• 作为产物：
  描述：

  丁炔二醇 、 ethyl 2-acetamido-2-propargyl-4-pentynoate 在 Wilkinson's catalyst 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以68%的产率得到ethyl 2-acetamido-5,6-bis(hydroxymethyl)indan-2-carboxylate
  参考文献：
  名称：

  Synthesis of constrained phenylalanine derivatives via a [2+2+2] cycloaddition strategy

  摘要：

  A simple synthesis of dialkyne building blocks (6,7,8 and 9) embodying amino acid moiety is described. The dialkyne 6 participated in a [2 + 2+ 2] cycloaddition reaction with various monoalkynes in presence of Wilkinson's catalyst to give 5- and 5,6-disubstitued indan-based alpha-amino acid derivates. Cobalt catalyst [e.g., CpCo(CO)(2)] has also been employed in the synthesis of various 2-indanyl glycine derivatives via co-trimerization reaction of the diyne building blocks 6 and 7 with several monoalkynes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00039-1

文献信息

• Synthesis of unsual α-amino acids via a 2+2+2 cycloaddition strategy
  作者：Sambasivarao Kotha、Enugurthi Brahmachary

  DOI：10.1016/s0040-4039(97)00663-1

  日期：1997.5

  A simple method for the preparation of di)ne building block 5 and its use in the synthesis of indane-based alpha-amino acid derivatives via a 2+2+2 cycloaddition strategy is reported. (C) 1997 Published by Elsevier Science Ltd.
• Cycloaddition approach to benzo-annulated indane-based α-amino acid derivatives
  作者：Sambasivarao Kotha、Arun Kumar Ghosh

  DOI：10.1016/j.tet.2004.09.051

  日期：2004.11

  Synthesis of various benzo-annulated indane-based alpha-amino acid (AAA) derivatives are reported via a [4+2] and [2+2+2] cycloaddition reactions as key steps. Here, o-xylylene based AAA moiety has been used as a reactive intermediate and by adopting this strategy various indane-based constrained AAA derivatives are prepared. (C) 2004 Elsevier Ltd. All rights reserved.