(1R,2S,4S)-(7-oxabicyclo[2.2.1]hept-2-yl)-carbamic acid ethyl ester | 1034079-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (1R,2S,4S)-(7-oxabicyclo[2.2.1]hept-2-yl)-carbamic acid ethyl ester
• 英文别名: ethyl N-(7-oxabicyclo[2.2.1]hept-2-yl)carbamate；ethyl (1R,2S,4S)-(7-oxabicyclo[2.2.1]hept-2-yl)-carbamate；(1r,2s,4s)-(7-Oxa-bicyclo[2.2.1]hept-2-yl)-carbamic acid ethyl ester；ethyl N-[(1R,2S,4S)-7-oxabicyclo[2.2.1]heptan-2-yl]carbamate
• CAS: 1034079-39-4
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: DJZIKKVPKWVRNA-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S)-(7-oxabicyclo[2.2.1]hept-2-yl)-carbamic acid ethyl ester 在 lithium aluminium tetrahydride 、 sodium hydroxide 、 水 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.33h， 生成 (1R,2S,4S)-(7-oxa-bicyclo[2.2.1]hept-2-yl)-amine hydrochloride
  参考文献：
  名称：

  PROCESS FOR THE MANUFACTURE OF 7-OXA-BICYCLO DERIVATIVES

  摘要：

  本发明涉及一种制备式I的7-氧杂双环衍生物的方法。

  公开号：

  US20080154043A1
• 作为产物：
  描述：

  (1R,2S,4S)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 在 肼 、 盐酸 、 sodium nitrite 作用下， 以 水 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1R,2S,4S)-(7-oxabicyclo[2.2.1]hept-2-yl)-carbamic acid ethyl ester
  参考文献：
  名称：

  PROCESS FOR THE MANUFACTURE OF 7-OXA-BICYCLO DERIVATIVES

  摘要：

  本发明涉及一种制备式I的7-氧杂双环衍生物的方法。

  公开号：

  US20080154043A1

文献信息

• Adaptation of an Exothermic and Acylazide-Involving Synthesis Sequence to Microreactor Technology
  作者：Luigi Rumi、Christophe Pfleger、Paul Spurr、Uwe Klinkhammer、Willi Bannwarth

  DOI：10.1021/op9000516

  日期：2009.7.17

  The original three-step batchwise synthesis of the pharmaceutical intermediate (IR,2S,4S)-(7-oxa-bicyclo[2.2.1]hept-2-yl)-carbamic acid ethyl ester (4) from (1R,2S,4S)-7-oxabicyclo[2.2.1]heptane-2-carboxyolic acid ethyl ester (1) encompassed a highly exothermic hydrazine quenching step as well as an acylazide intermediate. After appropriately modifying the reaction conditions, all three steps could be adapted to a microreactor system and a continuous process which permitted the desired carbamate 4 to be prepared under safe operating conditions in yields of 96%, 94%, and 84% for the three individual steps.
• [EN] PROCESS FOR THE MANUFACTURE OF 7-OXA-BICYCLO DERIVATIVES<br/>[FR] PROCÉDÉ DE FABRICATION DE DÉRIVÉS 7-OXA-BICYCLO
  申请人：HOFFMANN LA ROCHE

  公开号：WO2008077809A1

  公开（公告）日：2008-07-03

  [EN] The present invention relates to a process for the manufacture of the 7-oxabicyclo derivative of the formula (I).
  [FR] La présente invention porte sur un procédé de fabrication du dérivé 7-oxabicyclo de la formule (I).
• Enantioselective synthesis of (1R,2S,4S)-7-oxabicyclo[2.2.1]heptan-2-exo-carboxylic acid
  作者：Beat Wirz、Paul Spurr、Christophe Pfleger

  DOI：10.1016/j.tetasy.2009.12.030

  日期：2010.2

  A scalable enantioselective access to (1R,2S,4S)-7-oxabicyclo[2.2.1]heptan-2-exo-carboxylic acid 7, a key precursor in the synthesis of A2a receptor antagonist 1 by means of an enzymatic resolution of the respective butyl ester with lipase A from Candida antarctica, is described. (C) 2010 Elsevier Ltd. All rights reserved.
• PROCESS FOR THE MANUFACTURE OF 7-OXA-BICYCLO DERIVATIVES
  申请人：Spurr Paul

  公开号：US20080154043A1

  公开（公告）日：2008-06-26

  The present invention relates to a process for the manufacture of the 7-oxabicyclo derivative of the formula I

  本发明涉及一种制备式I的7-氧杂双环衍生物的方法。