tert-butyl N-[(4-methoxyphenyl)methyl]-N-(4-methylidenecyclohexyl)carbamate | 1228150-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl N-[(4-methoxyphenyl)methyl]-N-(4-methylidenecyclohexyl)carbamate
• CAS: 1228150-06-8
• 化学式: C₂₀H₂₉NO₃
• 分子量: 331.455
• InChiKey: SASDVTCRWIVFCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(4-methoxyphenyl)methyl]-N-(4-methylidenecyclohexyl)carbamate 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以80%的产率得到
  参考文献：
  名称：

  The design of efficient and selective routes to a key 1,4-cis-substituted cyclohexylamide intermediate

  摘要：

  This Letter describes the synthetic challenges in synthesising key 1,4-cis-substituted cyclohexylamide intermediate 1 for our research programme. Five different routes address the major issues of selectivity to afford the cis product in isomerically pure form and in high yield. Major purification issues were also encountered upon scaling some of the routes. The merits of the diverse routes are assessed and the reasoning given for which one was ultimately used for large-scale synthesis of 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.083
• 作为产物：
  描述：

  tert-butyl (4-methoxybenzyl)(4-oxocyclohexyl)carbamate 、 甲基三苯基碘化膦 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以76%的产率得到tert-butyl N-[(4-methoxyphenyl)methyl]-N-(4-methylidenecyclohexyl)carbamate
  参考文献：
  名称：

  The design of efficient and selective routes to a key 1,4-cis-substituted cyclohexylamide intermediate

  摘要：

  This Letter describes the synthetic challenges in synthesising key 1,4-cis-substituted cyclohexylamide intermediate 1 for our research programme. Five different routes address the major issues of selectivity to afford the cis product in isomerically pure form and in high yield. Major purification issues were also encountered upon scaling some of the routes. The merits of the diverse routes are assessed and the reasoning given for which one was ultimately used for large-scale synthesis of 1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.083

文献信息

• The design of efficient and selective routes to a key 1,4-cis-substituted cyclohexylamide intermediate
  作者：Christopher Barfoot、Gerald Brooks、David T. Davies、John Elder、Ilaria Giordano、Alan Hennessy、Graham Jones、Roger Markwell、Michael McGuire、Timothy Miles、Neil Pearson、Grant Spoors、Ravinder Sudini、Hengxu Wei、Jeffery Wood

  DOI：10.1016/j.tetlet.2010.03.083

  日期：2010.5

  This Letter describes the synthetic challenges in synthesising key 1,4-cis-substituted cyclohexylamide intermediate 1 for our research programme. Five different routes address the major issues of selectivity to afford the cis product in isomerically pure form and in high yield. Major purification issues were also encountered upon scaling some of the routes. The merits of the diverse routes are assessed and the reasoning given for which one was ultimately used for large-scale synthesis of 1. (C) 2010 Elsevier Ltd. All rights reserved.