(S)-2-azido-octane | 63493-25-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (S)-2-azido-octane
• 英文别名: (+)(S)-2-azido-octane；(+)(S)-2-Azido-octan；(S)-(+)-2-azidooctane；Octane, 2-azido-, (2S)-；(2S)-2-azidooctane
• CAS: 63493-25-4
• 化学式: C₈H₁₇N₃
• 分子量: 155.243
• InChiKey: OTIICZMNRMYWLV-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-azido-octane 在 甲醇 、 platinum(IV) oxide 作用下， 生成 (S)-2-氨基辛烷
  参考文献：
  名称：

  Levene; Rothen, Journal of Biological Chemistry, 1936, vol. 115, p. 426

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-(-)-2-iodooctane 在 甲醇 、 sodium azide 作用下， 生成 (S)-2-azido-octane
  参考文献：
  名称：

  Levene; Rothen, Journal of Biological Chemistry, 1936, vol. 115, p. 426

  摘要：

  DOI：

文献信息

• Efficient method for the one-pot azidation of alcohols using bis(p-nitrophenyl) phosphorazidate
  作者：Masanori Mizuno、Takayuki Shioiri、Masanori Mizuno

  DOI：10.1039/a705768g

  日期：——

  The direct stereoselective conversion of various alcohols and hexopyranoses into the corresponding alkyl azides and glycosyl azides, respectively, is efficiently accomplished by using bis(p-nitrophenyl) phosphorazidate and DBU.

  使用双（对硝基苯基）磷酸酰肼和DBU，可以高效地将各种醇和己糖吡喃转化为相应的烷基叠氮化物和糖苷叠氮化物。
• Process for the preparation of azide derivatives
  申请人：Eisai Co., Ltd.

  公开号：US05986088A1

  公开（公告）日：1999-11-16

  A process for the preparation of azide derivatives useful as drugs, perfumes or intermediates of dyes by reacting an alcohol derivative with di-p-nitrophenyl phosphorazidate in the presence of 1,8-diazabicyclo[5.4.0]-7-undecene.

  一种制备偶氮衍生物的方法，可用作药物、香料或染料中间体，通过在1,8-二氮杂双环[5.4.0]-7-十一烯存在下，将醇衍生物与二对硝基苯磷酰叠氮酸酯反应。
• Stereochemistry of two-phase and substrate-reagent ion-pair reactions of betylates: complete inversion in the synthesis of halogen, sulfur, and nitrogen derivatives from R-(-)-2-octanol
  作者：J.F. King、M. Aslam、J.D. Lock

  DOI：10.1016/s0040-4039(01)95478-4

  日期：1979.1

  Conversion of a chiral secondary alcohol into a chiral halogen, sulfur or nitrogen derivative may be conveniently carried out by way of a “betylate” ester. The overall reaction gives reasonable (40–40%) yields with high stereoselectivity (100% inversion in seven or eight examples).

  手性仲醇向手性卤素，硫或氮衍生物的转化可以通过“山y酸酯”酯方便地进行。总体反应可得到合理的（40–40％）的收率，且具有高的立体选择性（在七个或八个示例中为100％倒置）。
• Betylates. 3. Preparative nucleophilic substitution by way of [2]-, [3]-, and [4]betylates. Stoichiometric phase transfer and substrate-reagent ion-pair (SRIP) reactions of betylates
  作者：J. F. King、S. M. Loosmore、M. Aslam、J. D. Lock、M. J. McGarrity

  DOI：10.1021/ja00389a038

  日期：1982.12
• CsF in organic synthesis. Inversion of secondary mesylates and tosylates
  作者：Junzo Otera、Koichi Nakazawa、Koichi Sekoguchi、Akihiro Orita

  DOI：10.1016/s0040-4020(97)00900-9

  日期：1997.10

  Clean inversion of secondary mesylates and tosylates is effected by CsF in DMF. A variety of oxygen-, sulfur-, nitrogen-, and carbon-nucleophiles are employable. The reaction conditions have been optimized. The use of CsF in DMF is crucial and the reaction proceeds on the surface of solid CsF. It is suggested that hydrogen bonding between CsF and an active hydrogen of nucleophiles is responsible for the smooth reaction. Cesium carbonate fails to give rise to high specificity of inversion indicative of superiority of CsF. (C) 1997 Elsevier Science Ltd.