benzyl naphthalen-2-yl carbonate | 7107-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: benzyl naphthalen-2-yl carbonate
• 英文别名: Benzyl-<2>naphthyl-carbonat
• CAS: 7107-60-0
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: XEADQPXELJVMIT-UHFFFAOYSA-N

物化性质

• 熔点：
  71.0-71.5 °C
• 沸点：
  447.4±28.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl naphthalen-2-yl carbonate 在 甲醇 、 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 反应 0.25h， 以85%的产率得到2-萘酚
  参考文献：
  名称：

  Development of a novel protocol for chemoselective deprotection of N/O-benzyloxycarbonyl (Cbz) at ambient temperature

  摘要：

  A novel protocol for the deprotection of N-benzyloxycarbonyl and O-benzyloxycarbonyl groups by nickel boride generated in situ from NaBH4 and NiCl(2)6H(2)O in methanol at room temperature has been developed to give the corresponding amines and phenols. This protocol is chemoselective as groups like chloro, bromo, amide, ester, pyridine, and tert-butyloxycarbonyl moiety are unaffected under these conditions. The deprotection has also been validated in gram scale reactions, to establish the wider appropriateness of this protocol.

  DOI：

  10.1007/s00706-018-2276-x
• 作为产物：
  描述：

  sodium benzyloxycarbonyl thiosulfate 、 2-萘酚 以 水 为溶剂， 生成 benzyl naphthalen-2-yl carbonate
  参考文献：
  名称：

  Caldwell,J.B. et al., Australian Journal of Chemistry, 1966, vol. 19, p. 1297 - 1298

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Decarboxylative Carbonylative Transformation of Benzyl Aryl Carbonates: Direct Synthesis of Aryl 2-Arylacetates
  作者：Jian-Xing Xu、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.8b02631

  日期：2018.9.21

  A procedure on palladium-catalyzed decarboxylative alkoxycarbonylation of carbonates for the synthesis of aryl 2-arylacetates has been developed. A broad range of aryl 2-arylacetates were obtained in good yields under mild conditions under a carbon monoxide atmosphere. Interestingly, other alcohols can be added as nucleophiles as well, and the corresponding esters were also obtained in good yields

  已经开发了钯催化碳酸酯的脱羧烷氧基羰基化反应以合成芳基2-芳基乙酸酯的方法。在温和的条件下，在一氧化碳气氛下，以良好的收率获得了广泛的2-芳基乙酸芳基酯。有趣的是，也可以添加其他醇作为亲核试剂，并且也以高收率获得了相应的酯。
• Caldwell,J.B. et al., Australian Journal of Chemistry, 1966, vol. 19, p. 1297 - 1298
  作者：Caldwell,J.B. et al.

  DOI：——

  日期：——
• Development of a novel protocol for chemoselective deprotection of N/O-benzyloxycarbonyl (Cbz) at ambient temperature
  作者：Mohit Saroha、Komal Aggarwal、Gaurav Bartwal、Jitender M. Khurana

  DOI：10.1007/s00706-018-2276-x

  日期：2018.12

  A novel protocol for the deprotection of N-benzyloxycarbonyl and O-benzyloxycarbonyl groups by nickel boride generated in situ from NaBH4 and NiCl(2)6H(2)O in methanol at room temperature has been developed to give the corresponding amines and phenols. This protocol is chemoselective as groups like chloro, bromo, amide, ester, pyridine, and tert-butyloxycarbonyl moiety are unaffected under these conditions. The deprotection has also been validated in gram scale reactions, to establish the wider appropriateness of this protocol.