Carbamic acid, N-[(1S,2R)-2-azidocyclohexyl]-, 1,1-dimethylethyl ester

• 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: Carbamic acid, N-[(1S,2R)-2-azidocyclohexyl]-, 1,1-dimethylethyl ester
• 英文别名: tert-butyl N-(2-azidocyclohexyl)carbamate
• 化学式: C₁₁H₂₀N₄O₂
• 分子量: 240.305
• InChiKey: BYHGOVFTSYQQMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Carbamic acid, N-[(1S,2R)-2-azidocyclohexyl]-, 1,1-dimethylethyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 16.0h， 生成 左旋-反式-1,2-环己二胺盐酸盐 、 (1S,2S)-2-aminocyclohexan-1-ammonium chloride
  参考文献：
  名称：

  De Novo Synthesis of Tamiflu via a Catalytic Asymmetric Ring-Opening of meso-Aziridines with TMSN₃

  摘要：

  An asymmetric ring-opening reaction of meso-aziridines with TMSN3 was developed using a catalyst prepared from Y(OiPr)3 and chiral ligand 2 in a 1:2 ratio. Excellent enantioselectivity was realized from a wide range of substrates with a practical catalyst loading. The products were efficiently converted to enantiomerically enriched 1,2-diamines, which are versatile chiral building blocks for pharmaceuticals and chiral ligands. This reaction was applied to a catalytic asymmetric synthesis of Tamiflu, a very important anti-influenza drug containing a chiral 1,2-diamino functionality.

  DOI：

  10.1021/ja061696k
• 作为产物：
  描述：

  tert-butyl 7-azabicyclo<4.1.0>heptane-7-carboxylate 在 sodium azide 作用下， 以 水 、 乙腈 为溶剂， 反应 240.0h， 以59%的产率得到Carbamic acid, N-[(1S,2R)-2-azidocyclohexyl]-, 1,1-dimethylethyl ester
  参考文献：
  名称：

  环己基取代的β-卤代胺和叠氮鎓离子的合成，表征和亲核开环反应

  摘要：

  制备并表征了环己基取代的β-卤代胺和叠氮鎓离子。氮杂环丁烷离子的立体特异性开环被用于有效合成邻位胺，β-氨基酸和四氢异喹啉（THIQ）类似物。叠氮鎓离子和N-保护的氮丙啶类似物的亲核开环反应首次进行了比较研究。亲核反应的结果清楚地表明，与氮丙啶类似物相比，氮丙啶鎓离子对亲核开环的反应性明显更高。

  DOI：

  10.1016/j.tetlet.2014.12.101

文献信息

• Novel Compounds
  申请人：Cheng Yun-Xing

  公开号：US20070287695A1

  公开（公告）日：2007-12-13

  Compounds of Formulae I, or pharmaceutically acceptable salts thereof: wherein A 1 , A 2 , G 1 , G 2 G 3 , R 1 , R 2 , X, Y, Z, m, n and p are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  公式I的化合物，或其药用可接受的盐：其中A1、A2、G1、G2G3、R1、R2、X、Y、Z、m、n和p的定义如规范中所述，以及包括这些化合物的盐和药物组合物已经准备好。它们在治疗中很有用，特别是在疼痛管理方面。
• MUSCARINIC RECEPTOR AGONISTS THAT ARE EFFECTIVE IN THE TREATMENT OF PAIN, ALZHEIMER'S DISEASE AND SCHIZOPHRENIA.
  申请人：Astra Zeneca AB

  公开号：EP2035411A1

  公开（公告）日：2009-03-18
• US7956069B2
  申请人：——

  公开号：US7956069B2

  公开（公告）日：2011-06-07
• [EN] MUSCARINIC RECEPTOR AGONISTS THAT ARE EFFECTIVE IN THE TREATMENT OF PAIN, ALZHEIMER'S DISEASE AND SCHIZOPHRENIA.<br/>[FR] AGONISTES DES RÉCEPTEURS MUSCARINIQUES QUI SONT EFFICACES DANS LE TRAITEMENT DE LA DOULEUR, DE LA MALADIE D'ALZHEIMER ET DE LA SCHIZOPHRÉNIE
  申请人：ASTRAZENECA AB

  公开号：WO2007142583A1

  公开（公告）日：2007-12-13

  [EN] Compounds of Formulae I, or pharmaceutically acceptable salts thereof: wherein A¹, A², G¹, G², G³, R¹, R², X, Y, Z, m,n and p are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.
  [FR] La présente invention concerne des composés de la formule I, ou des sels pharmaceutiquement acceptables de ceux-ci, où: A¹, A², G¹, G², G³, R¹, R², X, Y, Z, m,n et p sont tels que définis dans les spécifications, ainsi que des sels et des compositions pharmaceutiques incluant les composés. Ces composés sont utiles dans la thérapie, en particulier dans la gestion de la douleur.
• De Novo Synthesis of Tamiflu via a Catalytic Asymmetric Ring-Opening of <i>meso</i>-Aziridines with TMSN₃
  作者：Yuhei Fukuta、Tsuyoshi Mita、Nobuhisa Fukuda、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1021/ja061696k

  日期：2006.5.1

  An asymmetric ring-opening reaction of meso-aziridines with TMSN3 was developed using a catalyst prepared from Y(OiPr)3 and chiral ligand 2 in a 1:2 ratio. Excellent enantioselectivity was realized from a wide range of substrates with a practical catalyst loading. The products were efficiently converted to enantiomerically enriched 1,2-diamines, which are versatile chiral building blocks for pharmaceuticals and chiral ligands. This reaction was applied to a catalytic asymmetric synthesis of Tamiflu, a very important anti-influenza drug containing a chiral 1,2-diamino functionality.