3-(benzyloxycarbonyl)aminobenzyl alcohol | 135429-73-1

• 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: 3-(benzyloxycarbonyl)aminobenzyl alcohol
• 英文别名: 3-(NHCbz)benzyl alcohol；NH-Cbz-3-aminobenzyl alcohol；3-(Cbz-Amino)benzyl alcohol；benzyl N-[3-(hydroxymethyl)phenyl]carbamate
• CAS: 135429-73-1
• 化学式: C₁₅H₁₅NO₃
• mdl: MFCD13206990
• 分子量: 257.289
• InChiKey: SYYGVDBUHXSATP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  3-(benzyloxycarbonyl)aminobenzyl alcohol 在 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 NH-Cbz-3-aminobenzaldehyde dimethyl acetal
  参考文献：
  名称：

  在碱性条件下由醛和醇制备缩醛†

  摘要：

  已经报道了在碱性条件下由不可烯化的醛和醇合成乙缩醛的一种新的，简单的方案。醇钠与相应的三氟乙酸酯一起促进了这种反应，利用三氟乙酸钠的形成作为缩醛形成的驱动力。通过与各种酸敏感保护基团的正交性以及与官能团的良好相容性，证明该方案的实用性，在酸性条件下由醛类和醇类合成时，可提供合成有用的乙缩醛以补充合成。

  DOI：

  10.1039/c8ob00017d
• 作为产物：
  描述：

  3-(苄氧基羰基氨基)苯甲酸 在 sodium tetrahydroborate 、 三乙胺 、 氯甲酸甲酯 作用下， 生成 3-(benzyloxycarbonyl)aminobenzyl alcohol
  参考文献：
  名称：

  Amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole as acid-stable prodrugs of potential inhibitors of H+K+ ATPase

  摘要：

  A series of amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole were prepared and found to possess gastric antisecretory activity on oral administration. (Glycylaminobenzyl)sulfinyl compound 23a, stable in artificial gastric juice (pH 1.2), was given orally to dogs. It was absorbed efficiently and converted into aniline derivative 7a which showed a very high plasma concentration. Compound 23a was hydrolyzed by the action of aminopeptidase present in plasma or the brush border fraction of the small intestine to release the terminal glycine. omicron-Aniline derivatives showed good activity in in vitro H+/K+-ATPase inhibition as well as in the inhibition of histamine stimulated acid secretion in isolated bullfrog gastric mucosa. Although these omicron-aniline derivatives showed no or weak gastric antisecretory activity in rat by id administration, they were active when administered ip. Therefore, these amino acid amides were considered to be acid stable prodrugs of proton pump inhibiting omicron-aniline derivatives. The mechanism of H+/K+-ATPase inhibition of 7a was also examined.

  DOI：

  10.1016/0223-5234(91)90024-h

文献信息

• A Practical in situ Generation of the Schwartz Reagent. Reduction of Tertiary Amides to Aldehydes and Hydrozirconation
  作者：Yigang Zhao、Victor Snieckus

  DOI：10.1021/ol403183a

  日期：2014.1.17

  A new, highly efficient in situ protocol (Cp2ZrCl2/LiAlH(OBu-t)3) is described for the generation of the Schwartz reagent which provides a convenient method for the amide to aldehyde reduction and the regioselective hydrozirconation–iodination of alkynes and alkenes. Highlighted are chemoselective reductions of benzamides derived by directed ortho metalation (DoM) chemistry, allowing the synthesis

  描述了一种新的高效原位实验方案（Cp 2 ZrCl 2 / LiAlH（OBu- t）3），用于产生Schwartz试剂，该试剂为酰胺到醛的还原以及炔烃的区域选择性加氢锆化加碘提供了便利的方法。和烯烃。突出显示的是通过定向邻位金属化（D o M）化学反应生成的苯甲酰胺的化学选择性还原，可合成有价值的1,2,3-取代的苯甲醛。单步三组分过程在非常短的反应时间内进行，显示出极好的官能团相容性，并使用廉价且长期保存的稳定还原剂。
• Green, Palladium-Catalyzed Synthesis of Benzylic<i>H</i>-Phosphinates from Hypophosphorous Acid and Benzylic Alcohols
  作者：Laëtitia Coudray、Jean-Luc Montchamp

  DOI：10.1002/ejoc.200800581

  日期：2008.8

  Benzylic alcohols cross-couple directly with concentrated H(3)PO(2) using Pd/xantphos (1 or 2 mol-%). Depending on the substrate, DMF at 110 degrees C, or t-AmOH at reflux with a Dean-Stark trap, can be used. A broad range of benzylic alcohols reacted successfully in moderate to good yields. The preparation of other organophosphorus compounds (phosphinic and phosphonic acids) is also demonstrated.Asymmetric

  苯甲醇直接与使用Pd / xantphos（1或2 mol％）的浓缩H（3）PO（2）交叉偶联。根据基材的不同，可以使用110摄氏度的DMF或带有迪安-斯达克榻分水器的t-AmOH回流。各种各样的苄醇以中等到良好的收率成功反应。还证明了其他有机磷化合物（次膦酸和膦酸）的制备。与（R）-1-（2-萘基）乙醇的不对称反应提供了77％ee的相应H-次膦酸。该方法提供了绿色，不含PC1（3）的苄基-H-次膦酸入口。
• Amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole as acid-stable prodrugs of potential inhibitors of H+K+ ATPase
  作者：K Hirai、H Koike、T Ishiba、S Ueda、I Makino、H Yamada、T Ichihashi、Y Mizushima、M Ishikawa、Y Ishihara、Y Hara、H Hirose、N Shima、M Doteuchi

  DOI：10.1016/0223-5234(91)90024-h

  日期：1991.3

  A series of amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole were prepared and found to possess gastric antisecretory activity on oral administration. (Glycylaminobenzyl)sulfinyl compound 23a, stable in artificial gastric juice (pH 1.2), was given orally to dogs. It was absorbed efficiently and converted into aniline derivative 7a which showed a very high plasma concentration. Compound 23a was hydrolyzed by the action of aminopeptidase present in plasma or the brush border fraction of the small intestine to release the terminal glycine. omicron-Aniline derivatives showed good activity in in vitro H+/K+-ATPase inhibition as well as in the inhibition of histamine stimulated acid secretion in isolated bullfrog gastric mucosa. Although these omicron-aniline derivatives showed no or weak gastric antisecretory activity in rat by id administration, they were active when administered ip. Therefore, these amino acid amides were considered to be acid stable prodrugs of proton pump inhibiting omicron-aniline derivatives. The mechanism of H+/K+-ATPase inhibition of 7a was also examined.
• Preparation of acetals from aldehydes and alcohols under basic conditions
  作者：Jakub Grabowski、Jarosław M. Granda、Janusz Jurczak

  DOI：10.1039/c8ob00017d

  日期：——

  A new, simple protocol for the synthesis of acetals under basic conditions from non-enolizable aldehydes and alcohols has been reported. Such reactivity is facilitated by a sodium alkoxide along with a corresponding trifluoroacetate ester, utilizing formation of sodium trifluoroacetate as a driving force for acetal formation. The usefulness of this protocol is demonstrated by its orthogonality with

  已经报道了在碱性条件下由不可烯化的醛和醇合成乙缩醛的一种新的，简单的方案。醇钠与相应的三氟乙酸酯一起促进了这种反应，利用三氟乙酸钠的形成作为缩醛形成的驱动力。通过与各种酸敏感保护基团的正交性以及与官能团的良好相容性，证明该方案的实用性，在酸性条件下由醛类和醇类合成时，可提供合成有用的乙缩醛以补充合成。