(1S,2S)-N,N'-di(tert-butoxycarbonyl)cyclohex-4-ene-1,2-diamine | 891831-15-5

• 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: (1S,2S)-N,N'-di(tert-butoxycarbonyl)cyclohex-4-ene-1,2-diamine
• 英文别名: (4S,5S)-4,5-bis(tert-butoxycarbonylamino)cyclohex-1-ene；(4S,5S)-4,5-bis(tert-butoxycarbonylamino)cyclohexene；di-tert-butyl ((1S,2S)-cyclohex-4-ene-1,2-diyl)dicarbamate；tert-butyl N-[(1S,6S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohex-3-en-1-yl]carbamate
• CAS: 891831-15-5
• 化学式: C₁₆H₂₈N₂O₄
• 分子量: 312.409
• InChiKey: IBBVWOZAKKWMOG-RYUDHWBXSA-N

物化性质

• 沸点：
  434.2±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S)-N,N'-di(tert-butoxycarbonyl)cyclohex-4-ene-1,2-diamine 在 selenium(IV) oxide 、 戴斯-马丁氧化剂 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (4R,5S)-4,5-bis(tert-butoxycarbonylamino)cyclohexen-3-one
  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：

  1,4-环己二烯 在 yttrium(III) isopropoxide 4-二甲氨基吡啶 、 sodium azide 、 叠氮基三甲基硅烷 、 碳酸氢钠 、 氯化铵 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 76.0h， 生成 (1S,2S)-N,N'-di(tert-butoxycarbonyl)cyclohex-4-ene-1,2-diamine
  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

文献信息

• THERAPEUTIC COMPOUNDS AND METHODS OF USE THEREOF
  申请人：GENENTECH, INC.

  公开号：US20190263786A1

  公开（公告）日：2019-08-29

  The invention provides a compound as described herein or a pharmaceutically acceptable salt thereof, and compositions containing such compounds and methods for using such compounds and compositions.

  本发明提供了一种如本文所述的化合物或其药用可接受的盐，以及含有该化合物的组合物和使用该化合物及组合物的方法。
• Therapeutic compounds and methods of use thereof
  申请人：GENENTECH, INC.

  公开号：US10457654B2

  公开（公告）日：2019-10-29

  The invention provides a compound of formula I: or a pharmaceutically acceptable salt thereof, wherein the variables X, Y1—Y5, R1, R2, R3, R4, and Het have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.

  本发明提供了一种式 I 的化合物： 或其药学上可接受的盐，其中变量 X、Y1-Y5、R1、R2、R3、R4 和 Het 的含义如本文所述，以及含有此类化合物的组合物和使用此类化合物及组合物的方法。
• Chemoenzymatic preparation of optically active trans- and cis-cyclohex-4-ene-1,2-diamine and trans-6-aminocyclohex-3-enol derivatives
  作者：F. Javier Quijada、Francisca Rebolledo、Vicente Gotor

  DOI：10.1016/j.tet.2012.05.087

  日期：2012.9

  Lipase from Burkholderia cepacia (PSL-C) effectively catalyzed the kinetic resolution of both racemic trans-N,N-diallylcyclohex-4-ene-1,2-diamine (+/-)-6 and its precursor trans-6-(diallylamino)cyclohex-3-enol (+/-)-5. The resulting optically active vicinal diamine and beta-amino alcohol were converted into a precursor of oseltamivir and a cis-cyclohex-4-ene-1,2-diamine derivative, respectively. (C) 2012 Elsevier Ltd. All rights reserved.
• Enhanced Rate and Selectivity by Carboxylate Salt as a Basic Cocatalyst in Chiral N-Heterocyclic Carbene-Catalyzed Asymmetric Acylation of Secondary Alcohols
  作者：Satoru Kuwano、Shingo Harada、Bubwoong Kang、Raphaël Oriez、Yousuke Yamaoka、Kiyosei Takasu、Ken-ichi Yamada

  DOI：10.1021/ja4055838

  日期：2013.8.7

  The rate and enantioselectivity of chiral NHC-catalyzed asymmetric acylation of alcohols with an adjacent H-bond donor functionality are remarkably enhanced in the presence of a carboxylate cocatalyst. The degree of the enhancement is correlated with the basicity of the carboxylate. With a cocatalyst and a newly developed electron-deficient chiral NHC, kinetic resolution and desymmetrization of cyclic diols and amino alcohols were achieved with extremely high selectivity (up to s = 218 and 99% ee, respectively) at a low catalyst loading (0.5 mol %). This asymmetric acylation is characterized by a unique preference for alcohols over amines, which are not converted into amides under the reaction conditions.
• J. Am. Chem. Soc. 2006, 128, 6312-6313
  作者：

  DOI：——

  日期：——