(1R,2S)-(+)-1-amino-2-decanol

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2S)-(+)-1-amino-2-decanol
• 英文别名: (2S)-1-aminodecan-2-ol
• 化学式: C₁₀H₂₃NO
• 分子量: 173.299
• InChiKey: BHWJEYCAUWCFDA-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-(+)-1-amino-2-decanol 在 盐酸 作用下， 以 甲醇 为溶剂， 以8.8 mg的产率得到
  参考文献：
  名称：

  The Configuration of Distaminolyne A is S: Quantitative Evaluation of Exciton Coupling Circular Dichroism of N,O- Bis-arenoyl-1-amino-2-alkanols

  摘要：

  The 2S configuration of the marine natural product distaminolyne A was recently disputed based upon total synthesis, yet paradoxically supported by a second independent total synthesis from a different research group. We now verify the 2S configuration of distaminolyne A by extensive chiroptical studies and support the veracity of the EC ECD method originally used to prove it. The origin of the apparent paradox appears to lie in the limits of precision of polarimetry in the context of weakly rotatory molecules, which strikes a cautionary note on the reliability of "reassignment" of natural product configurations based solely on specific rotation.

  DOI：

  10.1021/acs.jnatprod.8b00937
• 作为产物：
  描述：

  1,2-二甲基丁炔酯 在 ammonium hydroxide 、 (S,S)-Salen-Co(III)-OAc 作用下， 以 乙醇 、 水 为溶剂， 反应 17.0h， 生成 (1R,2S)-(+)-1-amino-2-decanol
  参考文献：
  名称：

  The Configuration of Distaminolyne A is S: Quantitative Evaluation of Exciton Coupling Circular Dichroism of N,O- Bis-arenoyl-1-amino-2-alkanols

  摘要：

  The 2S configuration of the marine natural product distaminolyne A was recently disputed based upon total synthesis, yet paradoxically supported by a second independent total synthesis from a different research group. We now verify the 2S configuration of distaminolyne A by extensive chiroptical studies and support the veracity of the EC ECD method originally used to prove it. The origin of the apparent paradox appears to lie in the limits of precision of polarimetry in the context of weakly rotatory molecules, which strikes a cautionary note on the reliability of "reassignment" of natural product configurations based solely on specific rotation.

  DOI：

  10.1021/acs.jnatprod.8b00937
• 作为试剂：
  描述：

  (6S)- and (6R)-SO2 adducts of 1(S),3(R)-bis(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5,7(E),10(19)-triene 在 吡啶 、 sodium dithionate 、 9-乙酰基蒽 、 (1R,2S)-(+)-1-amino-2-decanol 、 四丁基氟化铵 、 十六烷基三甲基氯化铵 、 碳酸氢钠 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 27.0h， 生成 他卡西醇
  参考文献：
  名称：

  一种他卡西醇的异构体杂质PY2及其制备方法和用途

  摘要：

  本发明公开了一种他卡西醇的异构体杂质PY2，即(1α,3β,5Z,7E,24S)‑9,10‑开环胆甾‑5,7,10(19)‑三烯‑1,3,24‑三醇，以及其制备方法，属于化学制药技术领域。本发明所述高纯度的他卡西醇的有关杂质PY2，可作他卡西醇成品检测分析中的杂质标准品，从而提升他卡西醇成品检测分析对杂质的准确定位和定性，有利于加强对该杂质的控制，进而提高他卡西醇成品质量。本发明提供的方法原料便宜易得，操作简单，重现性好，HPLC纯度≥99.5%。

  公开号：

  CN108017567A

文献信息

• Enantiomeric Variability of Distaminolyne A. Refinement of ECD and NMR Methods for Determining Optical Purity of 1-Amino-2-Alkanols
  作者：A. Pearce、Brent Copp、Tadeusz Molinski

  DOI：10.3390/molecules24010090

  日期：——

  coupled electronic circular dichroism (EC ECD) of the corresponding N,O-dibenzoyl derivative 1b; and chiral reagent derivatization of 1a with (S)- and (R)-α-methoxyphenylacetic acid (MPA), followed by ¹H-NMR analysis. Configuration and optical purity of 1a (%ee) was found to vary depending on the geographic distribution of ascidian colonies. An improved method for preparing N,O-diarenoyl derivatives of

  distaminolyne A (1a) 的示例配置；从海鞘类 Pseudodistoma opacum 和 P. cereum 中分离出来，并在新西兰的不同地点收集，通过两种方法进行了研究：相应的 N,O-二苯甲酰衍生物 1b 的激子耦合电子圆二色性（EC ECD）；以及用(S)-和(R)-α-甲氧基苯乙酸(MPA)对1a进行手性试剂衍生化，然后进行1H-NMR分析。发现 1a (%ee) 的结构和光学纯度随海鞘菌落的地理分布而变化。优化了1a的N,O-二芳酰基衍生物的制备方法。发现 EC ECD 方法在不同的 %ee 范围内与 MPA-NMR 方法互补。
• The Configuration of Distaminolyne A is <i>S</i>: Quantitative Evaluation of Exciton Coupling Circular Dichroism of <i>N</i>,<i>O</i>- Bis-arenoyl-1-amino-2-alkanols
  作者：Tadeusz F. Molinski、Mariam N. Salib、A. Norrie Pearce、Brent R. Copp

  DOI：10.1021/acs.jnatprod.8b00937

  日期：2019.5.24

  The 2S configuration of the marine natural product distaminolyne A was recently disputed based upon total synthesis, yet paradoxically supported by a second independent total synthesis from a different research group. We now verify the 2S configuration of distaminolyne A by extensive chiroptical studies and support the veracity of the EC ECD method originally used to prove it. The origin of the apparent paradox appears to lie in the limits of precision of polarimetry in the context of weakly rotatory molecules, which strikes a cautionary note on the reliability of "reassignment" of natural product configurations based solely on specific rotation.