Butyric acid (1S,2S)-2-azido-cyclohexyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Butyric acid (1S,2S)-2-azido-cyclohexyl ester
• 英文别名: [(1S,2S)-2-azidocyclohexyl] butanoate
• 化学式: C₁₀H₁₇N₃O₂
• 分子量: 211.264
• InChiKey: PYLAPGHGLGLGQG-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  40.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Butyric acid (1S,2S)-2-azido-cyclohexyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (1S,2S)-2-azidocyclohexanol
  参考文献：
  名称：

  通过酶促水解合成新型（+）-和（-）-反式-2-氨基环己醇

  摘要：

  通过使用脂肪酶将（±）-2-叠氮基环己酸酯进行酶水解并随后氢化，获得了反-2-氨基环己醇的两种对映体。

  DOI：

  10.1016/s0040-4039(00)82073-0
• 作为产物：
  描述：

  氧化环己烯 在 吡啶 、 4-二甲氨基吡啶 、 Candida cylindracea lipase 、 sodium azide 、 phosphate buffer 、 氯化铵 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 Butyric acid (1S,2S)-2-azido-cyclohexyl ester
  参考文献：
  名称：

  通过酶促水解合成新型（+）-和（-）-反式-2-氨基环己醇

  摘要：

  通过使用脂肪酶将（±）-2-叠氮基环己酸酯进行酶水解并随后氢化，获得了反-2-氨基环己醇的两种对映体。

  DOI：

  10.1016/s0040-4039(00)82073-0

文献信息

• (1<i>S</i>,2<i>R</i>/1<i>R</i>,2<i>S</i>)-Aminocyclohexyl Glycyl Thymine PNA:  Synthesis, Monomer Crystal Structures, and DNA/RNA Hybridization Studies
  作者：T. Govindaraju、Rajesh G. Gonnade、Mohan M. Bhadbhade、Vaijayanti A. Kumar、Krishna N. Ganesh

  DOI：10.1021/ol034933m

  日期：2003.8.1

  graphicThe synthesis of ethyl cis-(1S,2R/1R,2S)-2-aminocyclohex-1-yl-N-(thymin-1-yl-acetyl) glycinate (10a and 10b) via enzymatic resolution of the key racemic intermediate trans-2-azido cyclohexanols 3 is reported. The crystal structures of 10 show equatorial disposition of the tertiary amide group, with the torsion angle beta in the range 60-70degrees. The PNA oligomers incorporating these show differential effects in hybridizing with complementary DNA and RNA.
• FABER, KURT;HONIG, HELMUT;SEUFER-WASSERTHAL, PETER, TETRAHEDRON LETT., 29,(1988) N 16, 1903-1904
  作者：FABER, KURT、HONIG, HELMUT、SEUFER-WASSERTHAL, PETER

  DOI：——

  日期：——
• Synthesis and Evaluation of (1<i>S</i>,2<i>R</i>/1<i>R</i>,2<i>S</i>)-Aminocyclohexylglycyl PNAs as Conformationally Preorganized PNA Analogues for DNA/RNA Recognition
  作者：T. Govindaraju、Vaijayanti A. Kumar、Krishna N. Ganesh

  DOI：10.1021/jo035747x

  日期：2004.3.1

  Conformationally constrained cis-aminocyclohexylglycyl PNAs have been designed on the basis of stereospecific imposition of 1,2-cis-cyclohexyl moieties on the aminoethyl segment of aminoethylglycyl PNA (aegPNA). The introduction of the cis-cyclohexyl ring may allow the restriction of the torsion angle beta in the ethylenediamine segment to 60-70degrees that is prevalent in PNA(2):DNA and PNA:RNA complexes. The synthesis of the optically pure monomers (10a and 10b) is achieved by stereoselective enzymatic hydrolysis of an intermediate ester 2. The chiral PNA oligomers were synthesized with (1S,2R/1R,2S)-aminocyclohexylglycyI thymine monomers in the center and N-terminus of aegPNA. Differential gel shift retardation with one or more units of modified monomer units was observed as a result of hybridization of PNA sequences with complementary DNA sequences. Hybridization studies with complementary DNA and RNA sequences using UV-T-m measurements indicate that PNA with (1S,2R)-cyclohexyl stereochemistry enhances selective binding with RNA over DNA as compared to control aegPNA and PNA with the other (1R,2S) isomer.
• A novel and efficient synthesis of (+)- and (−)-trans-2-aminocyclohexanol by enzymatic hydrolysis
  作者：Kurt Faber、Helmut Hönig、Peter Seufer-Wasserthal

  DOI：10.1016/s0040-4039(00)82073-0

  日期：1988.1

  Both enantiomers of trans-2-aminocyclohexanol were obtained by enzymatic hydrolysis of (±)-2-azidocyclohexanoates using lipases and subsequent hydrogenation.

  通过使用脂肪酶将（±）-2-叠氮基环己酸酯进行酶水解并随后氢化，获得了反-2-氨基环己醇的两种对映体。