dodecyl 2-benzoylbenzoate | 185062-43-5

• 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: dodecyl 2-benzoylbenzoate
• CAS: 185062-43-5
• 化学式: C₂₆H₃₄O₃
• 分子量: 394.554
• InChiKey: HDJFAATYJMNCOE-UHFFFAOYSA-N

物化性质

• 沸点：
  496.8±18.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dodecyl 2-benzoylbenzoate 在 1,8-dimethoxypyrene 、 溶剂黄146 、 2-(4-甲氧基苯基)-1,3-二甲基-2H-苯并咪唑 作用下， 以 三氟甲苯 为溶剂， 反应 6.0h， 以93%的产率得到十二烷醇
  参考文献：
  名称：

  苯并咪唑啉-二甲氧基芘。一种有效的光诱导电子转移促进有机化合物还原转化的促进剂体系

  摘要：

  2-(对甲氧基苯基)-1,3-二甲基苯并咪唑啉 (ADMBI) 和 2-(邻羟基苯基)-1,3-二甲基苯并咪唑啉 (HPDMBI) 用作 1,8-二甲氧基芘 (1,8-DMP) 中的还原剂) 敏化的光致电子转移 (PET) 反应。该系统可有效用于 PET 诱导的各种有机底物的还原转化，包括 α,β-环氧酮、烯烃束缚的 2-溴甲基-1-四氢萘酮和邻烯丙氧基碘苯，以及脱保护反应十二烷基-2-苯甲酰苯甲酸酯和N-磺酰基吲哚。研究结果表明，1,8-DMP 是一种比以前使用的 9-甲基咔唑更有效的敏化剂，可用于 N-甲基-4-吡啶酯的脱保护。

  DOI：

  10.3987/com-08-s(f)94
• 作为产物：
  描述：

  邻苯甲酰苯甲酸 、 十二烷醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 为溶剂， 反应 48.0h， 以76%的产率得到dodecyl 2-benzoylbenzoate
  参考文献：
  名称：

  2-Benzoylbenzoic Acid:  A Photolabile Mask for Alcohols and Thiols

  摘要：

  Photolysis of 2-benzoylbenzoate esters of primary and secondary alcohols 1 in the presence of a hydrogen donor (2-isopropanol) or an electron donor (primary amines) produces the corresponding alcohol in high yield. The fate of the benzoate is dependent on the conditions used for the photoreaction. In 2-propanol, the ketyl radical that derives from photoreduction dimerizes, to afford the benzpinacol product 3,3'-diphenylbiphthalidyl, 5. In the presence of amines the product is 3-phenylphthalide, 6, a benzhydrol derivative which is the result of simple reduction of the ketone followed by lactonization. While the photoproduct of the benzoate-2-propanol reaction results from anticipated free radical chemistry, the amine-promoted reaction appears to result from a second, ''dark'', electron transfer process. We conclude that 2-benzoylbenzoic acid is an effective photolabile protecting group for primary and secondary alcohols, and preliminary studies indicate that thiols can be protected in an analogous way. Studies on the effect of benzophenone substituents and reaction solvent on the benzhydrol:benzpinacol product ratio provide mechanistic insight into the process.

  DOI：

  10.1021/jo961638p

文献信息

• AROMATIC ACYLATION WITH CYCLIC ANHYDRIDE FOR PLASTICIZER PRODUCTION
  申请人：ExxonMobil Research and Engineering Company

  公开号：US20140100383A1

  公开（公告）日：2014-04-10

  Provided is a process for making non-phthalate plasticizers, by acylating an aromatic compound with a succinic anhydride to form a keto-acid, and then esterifying the keto-acid with C 4 -C 13 OXO-alcohols to form a plasticizer compound. The aromatic rings of the aromatic compound may also be optionally hydrogenated.

  提供了一种制造非邻苯二甲酸酯塑化剂的过程，通过使用琥珀酸酐与芳香族化合物进行酰化反应，形成酮酸，然后通过与C4-C13氧化醇酯化反应形成塑化剂化合物。芳香族化合物的芳环也可以选择性地进行氢化。
• US8604114B2
  申请人：——

  公开号：US8604114B2

  公开（公告）日：2013-12-10
• US9512296B2
  申请人：——

  公开号：US9512296B2

  公开（公告）日：2016-12-06
• US9580571B2
  申请人：——

  公开号：US9580571B2

  公开（公告）日：2017-02-28
• 2-Benzoylbenzoic Acid:  A Photolabile Mask for Alcohols and Thiols
  作者：Paul B. Jones、Michael P. Pollastri、Ned A. Porter

  DOI：10.1021/jo961638p

  日期：1996.1.1

  Photolysis of 2-benzoylbenzoate esters of primary and secondary alcohols 1 in the presence of a hydrogen donor (2-isopropanol) or an electron donor (primary amines) produces the corresponding alcohol in high yield. The fate of the benzoate is dependent on the conditions used for the photoreaction. In 2-propanol, the ketyl radical that derives from photoreduction dimerizes, to afford the benzpinacol product 3,3'-diphenylbiphthalidyl, 5. In the presence of amines the product is 3-phenylphthalide, 6, a benzhydrol derivative which is the result of simple reduction of the ketone followed by lactonization. While the photoproduct of the benzoate-2-propanol reaction results from anticipated free radical chemistry, the amine-promoted reaction appears to result from a second, ''dark'', electron transfer process. We conclude that 2-benzoylbenzoic acid is an effective photolabile protecting group for primary and secondary alcohols, and preliminary studies indicate that thiols can be protected in an analogous way. Studies on the effect of benzophenone substituents and reaction solvent on the benzhydrol:benzpinacol product ratio provide mechanistic insight into the process.