tert-butyl 4-[N-(5-(2-benzyloxy-ethanoylamino)-6-cyanoindan-1-yl)amino]benzoate | 501170-80-5

• 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 4-[N-(5-(2-benzyloxy-ethanoylamino)-6-cyanoindan-1-yl)amino]benzoate
• 英文别名: tert-Butyl 4-[N-(5-(2-benzyloxyethanoylamino)-6-cyanoindan-1-yl)-amino]benzoate；tert-butyl 4-[[6-cyano-5-[(2-phenylmethoxyacetyl)amino]-2,3-dihydro-1H-inden-1-yl]amino]benzoate
• CAS: 501170-80-5
• 化学式: C₃₀H₃₁N₃O₄
• 分子量: 497.594
• InChiKey: ZLAAWMIONQAIBC-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195 °C
• 沸点：
  693.2±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-[N-(5-(2-benzyloxy-ethanoylamino)-6-cyanoindan-1-yl)amino]benzoate 在 palladium on activated charcoal sodium hydroxide 、 双氧水 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 22.83h， 生成 4-{N-[2-hydroxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid
  参考文献：
  名称：

  Cyclopenta[g]quinazolinone-based inhibitors of thymidylate synthase targeting α-folate receptor overexpressing tumours: synthetic approaches to 4-{N-[(6RS)-2-hydroxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid

  摘要：

  An advanced intermediate for the synthesis of cyclopenta[g]quinazolinone-based antifolates such as (6RS)-CB300945 was prepared by a convergent methodology. The oxo-functionality required for the formation of the C-6-N-10 bond in 4 was introduced in the initial steps of the synthesis, then the tricyclic ring was constructed and finally the propargyl group was introduced using the (propargyl)CO2(CO)(6)(+) complex without the need to protect the N-3-H or 2-hydroxymethyl functionalities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.092
• 作为产物：
  描述：

  5-benzyloxyacetamido-6-bromoindan-1-one 在 decaborane 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 tert-butyl 4-[N-(5-(2-benzyloxy-ethanoylamino)-6-cyanoindan-1-yl)amino]benzoate
  参考文献：
  名称：

  Cyclopenta[g]quinazolinone-based inhibitors of thymidylate synthase targeting α-folate receptor overexpressing tumours: synthetic approaches to 4-{N-[(6RS)-2-hydroxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid

  摘要：

  An advanced intermediate for the synthesis of cyclopenta[g]quinazolinone-based antifolates such as (6RS)-CB300945 was prepared by a convergent methodology. The oxo-functionality required for the formation of the C-6-N-10 bond in 4 was introduced in the initial steps of the synthesis, then the tricyclic ring was constructed and finally the propargyl group was introduced using the (propargyl)CO2(CO)(6)(+) complex without the need to protect the N-3-H or 2-hydroxymethyl functionalities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.092

文献信息

• [EN] PROCESS FOR THE PREPARATION OF CYCLOPENTA[g]QUINAZOLINE DERIVATIVES<br/>[FR] PROCEDE DE SYNTHESE
  申请人：BTG INT LTD

  公开号：WO2003020706A1

  公开（公告）日：2003-03-13

  Cyclopenta[g]quinazolines of formula (I), and esters and amides thereof may be made by reacting an ester or amide of formula (II), or a protected derivative thereof with a complex containing the (propargyl)Co2(CO)6+ion.

  公式(I)的环戊基[g]喹唑啉，以及其酯和酰胺可以通过将公式(II)的酯或酰胺或其保护衍生物与含有(propargyl)Co2(CO)6+离子的配合物反应而制得。
• Process for the preparation of cyclopenta[g]quinazoline derivatives
  申请人：——

  公开号：US20040266798A1

  公开（公告）日：2004-12-30

  Cyclopenta[g]quinazolines of formula (I), and esters and arnides thereof may be made by reacting an ester or amide of formula (II); or a protected derivative thereof with a complex containing the (propargyl)Co 2 (CO) 6 + ion. 1

  公式（I）的环戊[g]喹唑啉及其酯和酰胺可以通过将公式（II）的酯或酰胺或其保护衍生物与含（丙炔基）Co2（CO）6+离子的配合物反应而制得。
• PROCESS FOR THE PREPARATION OF CYCLOPENTA[G]QUINAZOLINE DERIVATIVES
  申请人：BTG International Limited

  公开号：EP1421069A1

  公开（公告）日：2004-05-26
• US7250511B2
  申请人：——

  公开号：US7250511B2

  公开（公告）日：2007-07-31
• Cyclopenta[g]quinazolinone-based inhibitors of thymidylate synthase targeting α-folate receptor overexpressing tumours: synthetic approaches to 4-{N-[(6RS)-2-hydroxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid
  作者：Vassilios Bavetsias、Elisa A. Henderson、Edward McDonald

  DOI：10.1016/j.tet.2006.11.092

  日期：2007.2

  An advanced intermediate for the synthesis of cyclopenta[g]quinazolinone-based antifolates such as (6RS)-CB300945 was prepared by a convergent methodology. The oxo-functionality required for the formation of the C-6-N-10 bond in 4 was introduced in the initial steps of the synthesis, then the tricyclic ring was constructed and finally the propargyl group was introduced using the (propargyl)CO2(CO)(6)(+) complex without the need to protect the N-3-H or 2-hydroxymethyl functionalities. (c) 2006 Elsevier Ltd. All rights reserved.