Deamination Reaction of Diastereomeric DL-2 (1-Phenylcyclohexyl) cyclohexylamine with Nitrous Acid

• KOBAYASHI TSUNEO

  Faculty of Pharmaceutical Sciences, Kyushu University Basic Research Laboratories, Toyo Rayon Co., Ltd.

• KAWAZOE YUICHI

  Faculty of Pharmaceutical Sciences, Kyushu University

• TAGUCHI TANEZO

  Faculty of Pharmaceutical Sciences, Kyushu University

抄録

DL-trans-and DL-cis-2-(1-Phenylcyclohexyl) cyclohexylamine (trans- and cis-II) were prepared from _DL-2-(1-phenylcyclohexyl) cyclohexanone (I) and submitted to deamination reaction with HNO₂, expecting steric government of 1-phenylcyclohexyl group as an extraordinarily bulky substituent. As a result, steric effect was observed more remarkably in the reaction of trans-II than of cis-II. On the way to completion of the reaction, cis-II nitrite was isolated as one of unusual examples. In addition, dehydration reaction of trans- and cis-alcohol derived from I and the Chugaev reaction of their xanthates were undertaken to prepare reference compounds for the identifications of products from the deamination reaction. All reactions involved in this study were mechanistically discussed.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 19 (6), 1178-1185, 1971

  公益社団法人 日本薬学会

キーワード

• Drug Discovery
• General Chemistry
• General Medicine

詳細情報

• CRID: 1390001204173852672
• NII論文ID: 130003766846
• DOI: 10.1248/cpb.19.1178
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/19/6/19_6_1178/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可