tert-butyl (1S,2R)-2-hydroxy-1-phenylpentylcarbamate | 1202798-61-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (1S,2R)-2-hydroxy-1-phenylpentylcarbamate
• 英文别名: tert-butyl N-[(1S,2R)-2-hydroxy-1-phenylpentyl]carbamate
• CAS: 1202798-61-5
• 化学式: C₁₆H₂₅NO₃
• 分子量: 279.379
• InChiKey: HYSRMNPLSBQDQF-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2R)-2-hydroxy-1-phenylpentylcarbamate 、 对甲苯磺酰氯 在 三氟乙酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到N-(2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of N-Activated Aziridines and N-Activated Azetidines by Tetraalkylammonium Halides

  摘要：

  A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH2Cl2 solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.

  DOI：

  10.1021/jo902244y
• 作为产物：
  描述：

  (S)-tert-butyl (2-oxo-1-phenylpentyl)carbamate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以99%的产率得到tert-butyl (1S,2R)-2-hydroxy-1-phenylpentylcarbamate
  参考文献：
  名称：

  脂肪醛与 N-Boc 保护的亚胺的催化不对称交叉氮杂-苯偶姻反应

  摘要：

  交叉：已开发出一种催化剂体系，允许脂肪醛和 N-Boc 保护的亚胺在交叉氮杂-安息香反应中直接不对称偶联（参见方案；Boc =叔丁氧基羰基）。活性催化剂显示出与亚胺快速反应，然而，作为助催化剂的酸的存在使该过程可逆并允许催化剂再生。

  DOI：

  10.1002/anie.201202442

文献信息

• Catalytic Asymmetric Cross-Aza-Benzoin Reactions of Aliphatic Aldehydes with<i>N</i>-Boc-Protected Imines
  作者：Daniel A. DiRocco、Tomislav Rovis

  DOI：10.1002/anie.201202442

  日期：2012.6.11

  Crossed: A catalyst system has been developed that allows the direct asymmetric coupling of aliphatic aldehydes and N‐Boc‐protected imines in a cross‐aza‐benzoin reaction (see scheme; Boc=tert‐butoxycarbonyl). The active catalyst is shown to react rapidly with the imine, however, the presence of an acid as co‐catalyst renders this process reversible and allows the regeneration of the catalyst.

  交叉：已开发出一种催化剂体系，允许脂肪醛和 N-Boc 保护的亚胺在交叉氮杂-安息香反应中直接不对称偶联（参见方案；Boc =叔丁氧基羰基）。活性催化剂显示出与亚胺快速反应，然而，作为助催化剂的酸的存在使该过程可逆并允许催化剂再生。
• BF₃·OEt₂-Mediated Highly Regioselective S_N2-Type Ring-Opening of <i>N</i>-Activated Aziridines and <i>N</i>-Activated Azetidines by Tetraalkylammonium Halides
  作者：Manas K. Ghorai、Amit Kumar、Deo Prakash Tiwari

  DOI：10.1021/jo902244y

  日期：2010.1.1

  A highly regioselective Lewis acid-mediated S(N)2-type ring-opening of N-sulfonylaziridines and azetidines with tetraalkylammonium halides in CH2Cl2 solution to afford 1,2- and 1,3-haloamines in excellent yields is described. An easy diastereoselective route toward substituted chiral N-tosylaziridines has been developed. The mechanism of ring-opening via S(N)2 pathway has been confirmed by the formation of chiral haloamines with excellent er and dr. Chloroamines obtained from 2,3-disubstituted aziridines were converted to the chiral N-tosylamines via radical dehalogenation.